JP2011219435A - ヒト幹細胞を肝細胞へと分化誘導する化合物 - Google Patents
ヒト幹細胞を肝細胞へと分化誘導する化合物 Download PDFInfo
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- CMPNIWQMRYYTMK-UHFFFAOYSA-O tricetinidin Natural products [O+]=1C2=CC(O)=CC(O)=C2C=CC=1C1=CC(O)=C(O)C(O)=C1 CMPNIWQMRYYTMK-UHFFFAOYSA-O 0.000 description 1
- HUPQFYTYUDCKFF-UHFFFAOYSA-K tripotassium 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one phosphate Chemical compound P(=O)([O-])([O-])[O-].OC=1C=C(C=CC1O)C=1OC2=CC(=CC(=C2C(C1O)=O)O)O.[K+].[K+].[K+] HUPQFYTYUDCKFF-UHFFFAOYSA-K 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
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Abstract
【解決手段】間葉系幹細胞の肝細胞への分化誘導剤であって、Wnt/β−カテニン経路を抑制する有機低分子量化合物を含む、分化誘導剤。
【選択図】図7
Description
第一に、特許文献1〜2では、非肝幹細胞から幹細胞を誘導するための蛋白質について説明されているが、分化誘導剤として蛋白製剤を用いているため、安定性・安全性などの面でさらなる改善の余地があった。
<間葉系幹細胞の肝細胞への分化誘導剤>
本実施形態に係る間葉系幹細胞の肝細胞への分化誘導剤は、Wnt/β−カテニン経路を抑制する有機低分子量化合物を含む、分化誘導剤である。この構成によれば、Wnt/β−カテニン経路を抑制する有機低分子量化合物を用いるので、蛋白製剤や核酸製剤に比べ安定性・安全性などの面で優れており、間葉系幹細胞から肝細胞への分化効率に優れる安全な分化誘導法を実現できる。
1.肝特異的転写因子発現
2.肝特異的蛋白発現
3.グリコーゲン合成
4.尿素合成
5.TCF活性によるWnt/βeta−catenin経路のシグナル強度をルシフェラーゼ活性で評価
本明細書において、「ヘキサクロロフェン」(hexachlorophene)とは、PubChemから引用すると、以下の特性を有する化合物であり、化学式(1)で表される。
Compound ID 3598
IUPAC: 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
Molecular Weight 406.90354[g/mol]
Molecular Formula C13H6Cl6O2
XLogP3 7.5
H-Bond Donor 2
H-Bond Acceptor 2
Where:
Tanimoto is the Tanimoto score, a fraction between 0 and 1.
AB is the count of bits set after bit-wise & of fingerprints A and B
A is the count of bits set in fingerprint A
B is the count of bits set in fingerprint B
1: CID: 3598
hexachlorophene; pHisoHex; Gamophen
IUPAC: 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
MW: 406.903540 g/mol | MF: C13H6Cl6O2
Tested in BioAssays: All: 505, Active: 114
Anti-Infective Agents, Local more
2: CID: 20372044
IUPAC: 3,4,6-trichloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]phenol
MW: 372.458480 g/mol | MF: C13H7Cl5O2
3: CID: 23669625
Isobac; Isobac 20; Caswell No. 566A
IUPAC: sodium 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenolate
MW: 428.885370 g/mol | MF: C13H5Cl6NaO2
4: CID: 22088194
MW: 406.903540 g/mol | MF: C13H6Cl6O2-2
5: CID: 74742
CID74742; 3,4,4’,5’,6,6’-Hexachloro-2,2’-methylenediphenol; Phenol, 3,4,4’,5’,6,6’-hexachloro-2,2’-methylenedi-
IUPAC: 2,3,4-trichloro-6-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
MW: 406.903540 g/mol | MF: C13H6Cl6O2
6: CID: 22954419
MW: 406.903540 g/mol | MF: C13H6Cl6O2
7: CID: 209168
Phenol, 2,2’-methylenebis(3,5,6-trichloro-; 2,2’-Methylenebis(3,5,6-trichlorophenol); CID209168
IUPAC: 2,3,5-trichloro-6-[(3,4,6-trichloro-2-hydroxyphenyl)methyl]phenol
MW: 406.903540 g/mol | MF: C13H6Cl6O2
8: CID: 23349392
IUPAC: 3,4,6-trichloro-2-[(2-hydroxyphenyl)methyl]phenol
MW: 303.568360 g/mol | MF: C13H9Cl3O2
9: CID: 5282359
CID5282359; C14203; 2,2’,3,3’,5,5’-Hexachloro-6-biphenylol
IUPAC: 3,4,6-trichloro-2-(2,3,5-trichlorophenyl)phenol
MW: 376.877560 g/mol | MF: C12H4Cl6O
本明細書において、「ケルセチン」(Quercetin)とは、PubChemから引用すると、以下の特性を有する化合物であり、化学式(2)で表される。
Compound ID 5280343
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
Molecular Weight 302.2357 [g/mol]
Molecular Formula C15H10O7
XLogP3 1.5
H-Bond Donor 5
H-Bond Acceptor 7
1: CID: 5280343
quercetin; Sophoretin; Meletin
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
Tested in BioAssays: All: 281, Active: 55
Antioxidants more
2: CID: 20670067
IUPAC: actinium; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
MW: 1437.374435 g/mol | MF: C15H10Ac5O7
3: CID: 5281614
Fisetin; Cotinin; Superfustel
IUPAC: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
Tested in BioAssays: All: 174, Active: 28
4: CID: 5281692
Robinetin; Norkanugin; 5-Deoxymyricetin
IUPAC: 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
Tested in BioAssays: All: 24, Active: 2
5: CID: 5284452
Quercetin dihydrate; quercetin; Quercetine dihydrate
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one dihydrate
MW: 338.266260 g/mol | MF: C15H14O9
Tested in BioAssays: All: 98, Active: 12
Antioxidants more
6: CID: 10818722
CID10818722; [2,3-dihydroxy-6-(3,5,7-trihydroxy-4-oxo-chromen-2-yl)phenyl]thallium
IUPAC: [2,3-dihydroxy-6-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl]thallium
MW: 505.611060 g/mol | MF: C15H9O7Tl
7: CID: 16212154
Quercetin hydrate; MLS001074343; MLS002153851
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one hydrate
MW: 320.250980 g/mol | MF: C15H12O8
Tested in BioAssays: All: 132, Active: 14
8: CID: 16213065
Fisetin; 5-Deoxyquercetin; Natural Brown- 1
IUPAC: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one hydrate
MW: 304.251580 g/mol | MF: C15H12O7
9: CID: 24187083
NSC58588; 7255-55-2
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; zirconium
MW: 393.459700 g/mol | MF: C15H10O7Zr
Tested in BioAssays: All: 1, Active: 0
10: CID: 25031947
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; selenium
MW: 381.195700 g/mol | MF: C15H10O7Se
11: CID: 12305312
IUPAC: 6,8-dideuterio-3,5,7-trihydroxy-2-(2,3,6-trideuterio-4,5-dihydroxyphenyl)chromen-4-one
MW: 307.266509 g/mol | MF: C15H10O7
12: CID: 21600688
IUPAC: 3,5,7-trihydroxy-2-(2,3,6-trideuterio-4,5-dihydroxyphenyl)chromen-4-one
MW: 305.254185 g/mol | MF: C15H10O7
13: CID: 23105025
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5-dihydroperoxy-7-hydroxychromen-4-one
MW: 334.234500 g/mol | MF: C15H10O9
14: CID: 5281672
myricetin; Cannabiscetin; Myricetol
IUPAC: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 318.235100 g/mol | MF: C15H10O8
Tested in BioAssays: All: 277, Active: 48
15: CID: 12309893
IUPAC: 8-deuterio-3,7-dihydroxy-2-(2,3,6-trideuterio-4,5-dihydroxyphenyl)chromen-4-one
MW: 290.260947 g/mol | MF: C15H10O6
16: CID: 25201643
myricetin
IUPAC: 2,6-dihydroxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenolate
MW: 317.227160 g/mol | MF: C15H9O8-
17: CID: 5280445
luteolin; Luteoline; Luteolol
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
Tested in BioAssays: All: 258, Active: 41
18: CID: 5321864
5,7,2’,3’-Tetrahydroxyflavone; LMPK12110137; CID5321864
IUPAC: 2-(2,3-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
19: CID: 18471844
ZINC14644152
IUPAC: 5,7-dihydroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
20: CID: 22339062
IUPAC: 3,5-dihydroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
21: CID: 25201972
luteolin; 5734-TETRAHYDROXYFLAVONE; 3’,4’,5,7-Tetrahydroxyflavone
IUPAC: 4-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenolate
MW: 285.228360 g/mol | MF: C15H9O6-
22: CID: 26034
5,7-Di-O-methylquercetin; BRN 0344074; CID26034
IUPAC: 2-(3,4-dihydroxyphenyl)-3-hydroxy-5,7-dimethoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
23: CID: 5281604
Azaleatin; 5-O-Methylquercetin; Quercetin 5-methyl ether
IUPAC: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
24: CID: 5281638
6-Hydroxykaempferol; CHEBI:563476; LMPK12112860
IUPAC: 3,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
25: CID: 5281691
Rhamnetin; 7-Methoxyquercetin; 7-Methylquercetin
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
Tested in BioAssays: All: 117, Active: 6
26: CID: 10598612
CID10598612; 2-(3,4-dihydroxy-2-iodo-phenyl)-3,5,7-trihydroxy-chromen-4-one
IUPAC: 2-(3,4-dihydroxy-2-iodophenyl)-3,5,7-trihydroxychromen-4-one
MW: 428.132230 g/mol | MF: C15H9IO7
27: CID: 15233950
LMPK12112802
IUPAC: 3,5,6,7-tetrahydroxy-2-phenylchromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
28: CID: 17840574
IUPAC: (3,5,6,7-tetrahydroxy-2-phenylchromen-4-ylidene)oxidanium
MW: 287.244240 g/mol | MF: C15H11O6+
29: CID: 24721675
IUPAC: 3,7-dihydroxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
30: CID: 25205335
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; platinum(4+); dichloride
MW: 568.219700 g/mol | MF: C15H10Cl2O7Pt+2
31: CID: 25206803
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; platinum(4+); chloride; hydrochloride
MW: 569.227640 g/mol | MF: C15H11Cl2O7Pt+3
32: CID: 5322065
7,3’,4’-Trihydroxyflavone; 3’,4’,7-Trihydroxyflavone; BRN 0253031
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
33: CID: 5393164
7,3,4,5-tetrahydroxyflavone; CHEBI:519698; LMPK12110051
IUPAC: 7-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
34: CID: 10517292
CID10517292; 3-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
IUPAC: 3-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
35: CID: 16662883
IUPAC: 2-(2,3-dihydroxyphenyl)-7-hydroxychromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
36: CID: 21158518
IUPAC: 7-hydroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
37: CID: 5281701
Tricetin; Spectrum_001591; SpecPlus_000826
IUPAC: 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
Tested in BioAssays: All: 63, Active: 9
38: CID: 12359024
IUPAC: 3,6,8-trideuterio-5,7-dihydroxy-2-(2,3,6-trideuterio-4,5-dihydroxyphenyl)chromen-4-one
MW: 292.273271 g/mol | MF: C15H10O6
39: CID: 12359025
IUPAC: 3-deuterio-5,7-dihydroxy-2-(2,3,6-trideuterio-4,5-dihydroxyphenyl)chromen-4-one
MW: 290.260947 g/mol | MF: C15H10O6
40: CID: 627207
CHEBI:347700; CID627207; 3-Hydroxy-2-(3,4-dihydroxyphenyl)-7-methoxy-4H-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-3-hydroxy-7-methoxychromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
41: CID: 5280417
3,7-Di-O-methylquercetin; CHEBI:18010; MolPort-001-742-139
IUPAC: 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
42: CID: 5280681
3-O-Methylquercetin; 3-Methoxy quercetin; Quercetin-3-methylether
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
Tested in BioAssays: All: 234, Active: 11
43: CID: 5281680
Quercetagetin; 6-Hydroxyquercetin; CHEBI:202888
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
MW: 318.235100 g/mol | MF: C15H10O8
44: CID: 5319492
Flavone der.; AIDS071769; CHEBI:219000
IUPAC: 2-(3,4-dihydroxyphenyl)-3,6,7-trihydroxychromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
45: CID: 5489501
3,5-Di-O-methylquercetin; LMPK12112730; CID5489501
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-dimethoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
46: CID: 10516160
CID10516160; 3,7,8-trihydroxy-2-phenyl-chromen-4-one
IUPAC: 3,7,8-trihydroxy-2-phenylchromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
47: CID: 15560442
LMPK12111605
IUPAC: 2-(3,4-dihydroxyphenyl)-3,7,8-trihydroxychromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
48: CID: 21676161
IUPAC: [2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] sulfate
MW: 381.290960 g/mol | MF: C15H9O10S-
49: CID: 21676163
IUPAC: [2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl] sulfate
MW: 381.290960 g/mol | MF: C15H9O10S-
50: CID: 21676164
IUPAC: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] sulfate
MW: 381.290960 g/mol | MF: C15H9O10S-
51: CID: 22239065
LMPK12111601; ZINC12359395
IUPAC: 3,7,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
52: CID: 24721178
IUPAC: 3,7,8-trihydroxy-2-(2-hydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
53: CID: 25202270
3-methoxyluteolin; 3-O-Methylquercetin; 3’,4’,5,7-Tetrahydroxy-3-methoxyflavone
IUPAC: 4-(5,7-dihydroxy-3-methoxy-4-oxochromen-2-yl)-2-hydroxyphenolate
MW: 315.254340 g/mol | MF: C16H11O7-
54: CID: 25203115
Quercetin 3-sulfate; CPD-1822
IUPAC: [5,7-dihydroxy-2-(3-hydroxy-4-oxidophenyl)-4-oxochromen-3-yl] sulfate
MW: 380.283020 g/mol | MF: C15H8O10S-2
55: CID: 25206804
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; platinum(4+); tetrachloride
MW: 639.125700 g/mol | MF: C15H10Cl4O7Pt
56: CID: 16113029
LMPK12112522
IUPAC: 3,5,7-trihydroxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one
MW: 318.235100 g/mol | MF: C15H10O8
57: CID: 15661823
ZINC04349582
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methylchromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
58: CID: 6477685
AIDS154808; CHEBI:480357; AIDS-154808
IUPAC: 2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5,7-dihydroxychromen-4-one
MW: 312.273580 g/mol | MF: C17H12O6
59: CID: 88281
5,3’,4’-Trihydroxyflavone; TNP00056; CHEBI:490257
IUPAC: 2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
Tested in BioAssays: All: 81, Active: 10
60: CID: 17851159
IUPAC: 5-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
61: CID: 147651
Quercetin trimethyl ether; ZINC00338058; CID147651
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trimethoxychromen-4-one
MW: 344.315440 g/mol | MF: C18H16O7
62: CID: 5280362
Quercetin 3-sulfate; quercetin 3-(hydrogen sulfate); CHEBI:17730
IUPAC: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] hydrogen sulfate
MW: 382.298900 g/mol | MF: C15H10O10S
63: CID: 5280544
Herbacetin; 8-Hydroxykaempferol; LMPK12113149
IUPAC: 3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
64: CID: 5281654
Isorhamnetin; 3-Methylquercetin; Isorhamnetol
IUPAC: 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
Tested in BioAssays: All: 18, Active: 2
65: CID: 5281679
Pinoquercetin; 6-C-Methylquercetin; LMPK12112292
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methylchromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
66: CID: 5281699
Tamarixetin; 4’-O-Methylquercetin; Quercetin 4’-methyl ether
IUPAC: 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
67: CID: 5320287
Ombuin; 4’,7-Dimethylquercetin; 7,4’-Di-O-methylquercetin
IUPAC: 3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
68: CID: 5320945
Rhamnazin; 3’,7-Dimethylquercetin; 7,3’-Di-O-methylquercetin
IUPAC: 3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
Tested in BioAssays: All: 61, Active: 1
69: CID: 5362017
8-Hydroxygalangin; 3,5,7,8-Tetrahydroxyflavone; BRN 0295943
IUPAC: 3,5,7,8-tetrahydroxy-2-phenylchromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
70: CID: 5388949
nchembio718-comp16; ZINC04731234; CID5388949
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-methylchromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
71: CID: 9839293
CHEBI:304347; LMPK12111567; CID9839293
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxychromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
72: CID: 10022760
LMPK12112305; CID10022760; 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-7-sulfooxy-chromene
IUPAC: [2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl] hydrogen sulfate
MW: 382.298900 g/mol | MF: C15H10O10S
73: CID: 11012936
CID11012936; 3,5-dihydroxy-2-(3-hydroxy-2-methoxy-phenyl)-7-methoxy-chromen-4-one
IUPAC: 3,5-dihydroxy-2-(3-hydroxy-2-methoxyphenyl)-7-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
74: CID: 14162696
LMPK12112547
IUPAC: 3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
75: CID: 15227607
LMPK12112548
IUPAC: 3,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
76: CID: 20504452
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; methoxymethane
MW: 348.304140 g/mol | MF: C17H16O8
77: CID: 21676162
LMPK12112306
IUPAC: [2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] hydrogen sulfate
MW: 382.298900 g/mol | MF: C15H10O10S
78: CID: 21676167
IUPAC: [5,7-dihydroxy-2-(4-hydroxy-3-sulfonatooxyphenyl)-4-oxochromen-3-yl] sulfate
MW: 460.346220 g/mol | MF: C15H8O13S2-2
79: CID: 21676170
IUPAC: [5,7-dihydroxy-2-(3-hydroxy-4-sulfonatooxyphenyl)-4-oxochromen-3-yl] sulfate
MW: 460.346220 g/mol | MF: C15H8O13S2-2
80: CID: 21676173
IUPAC: [3,5-dihydroxy-2-(3-hydroxy-4-sulfonatooxyphenyl)-4-oxochromen-7-yl] sulfate
MW: 460.346220 g/mol | MF: C15H8O13S2-2
81: CID: 23670118
CHEBI:604112; potassium 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl sulfate
IUPAC: potassium [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] sulfate
MW: 420.389260 g/mol | MF: C15H9KO10S
82: CID: 25164913
IUPAC: [2-hydroxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] hydrogen sulfate
MW: 382.298900 g/mol | MF: C15H10O10S
83: CID: 25202413
Isorhamnetin; 3-Methylquercetin; 3’-Methoxyquercetin
IUPAC: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-olate
MW: 315.254340 g/mol | MF: C16H11O7-
84: CID: 25206967
IUPAC: azane; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; platinum(2+); dichloride
MW: 585.250220 g/mol | MF: C15H13Cl2NO7Pt
85: CID: 44472542
IUPAC: azane; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; platinum
MW: 531.374740 g/mol | MF: C15H16N2O7Pt
86: CID: 5319731
5-Methylmyricetin; LMPK12112555; CID5319731
IUPAC: 3,7-dihydroxy-5-methoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
87: CID: 14376433
LMPK12113049
IUPAC: 3,5,6,7-tetrahydroxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
MW: 334.234500 g/mol | MF: C15H10O9
88: CID: 44259636
LMPK12112664
IUPAC: 3,5-dihydroxy-7-methoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
89: CID: 5280616
2’-hydroxypseudobaptigenin; CID5280616; C03662
IUPAC: 7-hydroxy-2-(2,3,4,5-tetrahydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
90: CID: 5281605
baicalein; 5,6,7-Trihydroxyflavone; Biacalein
IUPAC: 5,6,7-trihydroxy-2-phenylchromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
Tested in BioAssays: All: 120, Active: 30
Prostaglandin Antagonists more
91: CID: 5281642
6-Hydroxyluteolin; Demethylpedalitin; 6-OH-Luteolin
IUPAC: 2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxychromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
92: CID: 5281697
Scutellarein; Isocarthamidin; Flavonoid
IUPAC: 5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
93: CID: 5318214
Hydroxygenkwanin; 7-O-Methylluteolin; MEGxp0_000798
IUPAC: 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
94: CID: 5702782
baicalein; 5,6,7-Trihydroxyflavone; OR1525T
IUPAC: 5,6,7-trihydroxy-2-phenylchromen-4-one hydrate
MW: 288.252180 g/mol | MF: C15H12O6
Prostaglandin Antagonists more
95: CID: 13964548
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dimethoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
96: CID: 13964550
LMPK12110965
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
97: CID: 18372862
IUPAC: 2-(3,4-dihydroxyphenyl)-3-hydroxy-5-methoxychromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
98: CID: 5281649
Isoetin; LMPK12110940; 5,7,2’,4’,5’-Pentahydroxyflavone
IUPAC: 5,7-dihydroxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
99: CID: 6477684
AIDS154807; CHEBI:480359; AIDS-154807
IUPAC: 2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-7-hydroxychromen-4-one
MW: 296.274180 g/mol | MF: C17H12O5
100: CID: 10636768
CHEBI:185726; CID10636768; 2-(3,4-Dihydroxy-benzyl)-7-hydroxy-chromen-4-one
IUPAC: 2-[(3,4-dihydroxyphenyl)methyl]-7-hydroxychromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
101: CID: 12417670
IUPAC: 2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
102: CID: 22507438
IUPAC: 2-(2,3,4-trihydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
103: CID: 628780
CID628780; 3-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4H-chromen-4-one
IUPAC: 3-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
104: CID: 4125009
CID4125009; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one
MW: 438.469740 g/mol | MF: C25H26O7
105: CID: 5280402
Quercetin 3,3’-bissulfate; CHEBI:17875; LMPK12112308
IUPAC: [5,7-dihydroxy-2-(4-hydroxy-3-sulfooxyphenyl)-4-oxochromen-3-yl] hydrogen sulfate
MW: 462.362100 g/mol | MF: C15H10O13S2
106: CID: 5280403
Quercetin 3,4’-bissulfate; CHEBI:18030; LMPK12112309
IUPAC: [5,7-dihydroxy-2-(3-hydroxy-4-sulfooxyphenyl)-4-oxochromen-3-yl] hydrogen sulfate
MW: 462.362100 g/mol | MF: C15H10O13S2
107: CID: 5280647
Gossypetin; Articulatidin; Equisporol
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxychromen-4-one
MW: 318.235100 g/mol | MF: C15H10O8
Tested in BioAssays: All: 54, Active: 8
108: CID: 5316900
Quercetin der.; 3,3’-Dimethylquercetin; 3,3’-Dimethoxyquercetin
IUPAC: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
109: CID: 5378244
LMPK12111569; CID5378244; 3,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
IUPAC: 3,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
110: CID: 5380905
ACon1_001466; CHEBI:221146; MolPort-001-741-117
IUPAC: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
Tested in BioAssays: All: 1, Active: 0
111: CID: 5481966
Gancaonin P; AIDS095976; CHEBI:565528
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
MW: 370.352720 g/mol | MF: C20H18O7
112: CID: 5482101
Geraldol; SPECTRUM1505149; BIDF1020
IUPAC: 3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
Tested in BioAssays: All: 52, Active: 3
113: CID: 6452329
M7HEQ; 7-O-beta-Hydroxyethylquercetin; 7-O-(beta-Hydroxyethyl)quercetin
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-(2-hydroxyethoxy)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
114: CID: 9799499
CHEBI:420898; ZINC03918592; CID9799499
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
MW: 370.352720 g/mol | MF: C20H18O7
115: CID: 9949390
CHEBI:303634; CID9949390; 2-(3,4-Dihydroxy-phenyl)-3-hydroxy-7-(2-hydroxy-ethoxy)-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-3-hydroxy-7-(2-hydroxyethoxy)chromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
116: CID: 10004518
CID10004518; 3,5-dihydroxy-2-(3-hydroxy-4-sulfooxy-phenyl)-4-oxo-7-sulfooxy-chromene
IUPAC: [3,5-dihydroxy-2-(3-hydroxy-4-sulfooxyphenyl)-4-oxochromen-7-yl] hydrogen sulfate
MW: 462.362100 g/mol | MF: C15H10O13S2
117: CID: 10050405
CID10050405; 2-(3,4-dihydroxyphenyl)-7-dodecoxy-3,5-dihydroxy-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-7-dodecoxy-3,5-dihydroxychromen-4-one
MW: 470.554660 g/mol | MF: C27H34O7
118: CID: 10895435
CHEBI:565814; CID10895435; 5,7,3’,4’-tetrahydroxy-6-geranylflavono
IUPAC: 2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5,7-trihydroxychromen-4-one
MW: 438.469740 g/mol | MF: C25H26O7
119: CID: 12988287
LMPK12112307
IUPAC: [2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3-sulfooxychromen-7-yl] hydrogen sulfate
MW: 462.362100 g/mol | MF: C15H10O13S2
120: CID: 15895793
LMPK12111579
IUPAC: 3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
121: CID: 17918606
IUPAC: 3,5,6,7,8-pentahydroxy-2-(2-hydroxyphenyl)chromen-4-one
MW: 318.235100 g/mol | MF: C15H10O8
122: CID: 21633676
LMPK12112866
IUPAC: 3,5,6,7-tetrahydroxy-2-(4-methoxyphenyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
123: CID: 23320229
IUPAC: 2-(3,4-dihydroxyphenyl)-3-ethoxy-7-hydroxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
124: CID: 24206515
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxychromen-4-one trihydrate
MW: 370.308120 g/mol | MF: C16H18O10
125: CID: 25201917
334578-HEXAHYDROXYFLAVONE; 3,3’,4’,5,7,8-Hexahydroxyflavone; 2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxochromen-8-olate
MW: 317.227160 g/mol | MF: C15H9O8-
126: CID: 44259330
LMPK12112314
IUPAC: [4-(3,5-dihydroxy-7-hydroxysulfonothioyloxy-4-oxochromen-2-yl)-2-hydroxyphenyl] hydrogen sulfate
MW: 478.427700 g/mol | MF: C15H10O12S3
127: CID: 44259518
LMPK12112520
IUPAC: 3,5,7-trihydroxy-2-(3-hydroxy-2,4-dimethoxyphenyl)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
128: CID: 44260065
LMPK12113327
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5,6,7,8-pentahydroxychromen-4-one
MW: 334.234500 g/mol | MF: C15H10O9
129: CID: 24721651
IUPAC: 5-hydroxy-3,7-dimethoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
130: CID: 25087106
Peflavit; Pentahydroxyflavone; 54077-18-8
IUPAC: 3,5,6,7,8-pentahydroxy-2-phenylchromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
131: CID: 25202871
quercetin-3,4-bissulfate; quercetin-3,4’-bissulfate; QUERCETIN-34-BISSULFATE
IUPAC: [2-hydroxy-4-(7-hydroxy-5-oxido-4-oxo-3-sulfonatooxychromen-2-yl)phenyl] sulfate
MW: 459.338280 g/mol | MF: C15H7O13S2-3
132: CID: 44259709
LMPK12112779
IUPAC: 5,7-dihydroxy-3-methoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
133: CID: 676310
TNP00054; CHEBI:473681; CID676310
IUPAC: 7,8-dihydroxy-2-(3-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
Tested in BioAssays: All: 81, Active: 10
134: CID: 688798
7,8,3’,4’-tetrahydroxyflavone; 3’,4’,7,8-Tetrahydroxyflavone; CHEBI:473674
IUPAC: 2-(3,4-dihydroxyphenyl)-7,8-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
135: CID: 5353357
6,7-dihydroxyflavone; 6,7-dihydroxy flavone; DivK1c_000421
IUPAC: 6,7-dihydroxy-2-phenylchromen-4-one
MW: 254.237500 g/mol | MF: C15H10O4
Tested in BioAssays: All: 86, Active: 5
136: CID: 5393155
ZINC00057757; CID5393155
IUPAC: 6,7-dihydroxy-2-(3-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
137: CID: 10355753
CHEBI:576113; CID10355753; 6,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
IUPAC: 6,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
138: CID: 10493280
CHEBI:303856; CID10493280; 2-(3,4-dihydroxyphenyl)-7-methoxy-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-7-methoxychromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
139: CID: 10532672
CID10532672; 2-(3,4-dihydroxy-2-iodo-phenyl)-3,5,7-trihydroxy-6,8-diiodo-chromen-4-one
IUPAC: 2-(3,4-dihydroxy-2-iodanylphenyl)-3,5,7-trihydroxy-6,8-bis(iodanyl)chromen-4-one
MW: 691.930253 g/mol | MF: C15H7I3O7
140: CID: 10556475
CID10556475; 2-(3,4-dihydroxy-2-iodo-phenyl)-3,5,7-trihydroxy-6,8-diiodo-chromen-4-one
IUPAC: 2-(3,4-dihydroxy-2-iodophenyl)-3,5,7-trihydroxy-6,8-diiodochromen-4-one
MW: 679.925290 g/mol | MF: C15H7I3O7
141: CID: 11347622
CID11347622; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(hydroxymethyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
142: CID: 18542127
IUPAC: 2-(2,3-dihydroxyphenyl)-7-methoxychromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
143: CID: 21725618
IUPAC: [2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl] sulfate
MW: 365.291560 g/mol | MF: C15H9O9S-
144: CID: 22138200
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(2,2,2-trihydroxyethyl)chromen-4-one
MW: 362.287660 g/mol | MF: C17H14O9
145: CID: 24721082
IUPAC: 3,6-dihydroxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
146: CID: 24721539
IUPAC: 2-(3,4-dihydroxyphenyl)-6,7-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
147: CID: 25227000
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(methoxymethyl)chromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
148: CID: 44610309
IUPAC: 2-(3,4-dihydroxyphenyl)-5-ethoxy-7-hydroxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
149: CID: 44610477
IUPAC: 2-(3,4-dihydroxyphenyl)-7-ethoxy-5-hydroxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
150: CID: 25030204
IUPAC: 7-hydroxy-5-methoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
151: CID: 25189611
IUPAC: 2-(3-fluoro-4,5-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
MW: 304.226763 g/mol | MF: C15H9FO6
152: CID: 6477683
AIDS154806; CHEBI:480360; AIDS-154806
IUPAC: 2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxychromen-4-one
MW: 296.274180 g/mol | MF: C17H12O5
153: CID: 9860659
CID9860659; 3,5,7-trihydroxy-2-(3-hydroxyphenyl)chromen-4-one
IUPAC: 3,5,7-trihydroxy-2-(3-hydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
154: CID: 632128
CHEBI:222167; CID632128; LMPK12112763
IUPAC: 2-(3-hydroxy-4-methoxyphenyl)-3,5,7-trimethoxychromen-4-one
MW: 358.342020 g/mol | MF: C19H18O7
155: CID: 5280631
Quercetin 3,3’,7-trissulfate; CHEBI:16557; LMPK12112310
IUPAC: [2-hydroxy-5-(5-hydroxy-4-oxo-3,7-disulfooxychromen-2-yl)phenyl] hydrogen sulfate
MW: 542.425300 g/mol | MF: C15H10O16S3
156: CID: 5280632
Quercetin 3,4’,7-trissulfate; CHEBI:28167; LMPK12112311
IUPAC: [2-hydroxy-4-(5-hydroxy-4-oxo-3,7-disulfooxychromen-2-yl)phenyl] hydrogen sulfate
MW: 542.425300 g/mol | MF: C15H10O16S3
157: CID: 5280682
Ayanin; 3,7,4’-Tri-O-methylquercetin; 3,7,4’-trimethylquercetin
IUPAC: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one
MW: 344.315440 g/mol | MF: C18H16O7
Tested in BioAssays: All: 59, Active: 0
158: CID: 5281677
Pachypodol; CHEBI:373037; NSC 168805
IUPAC: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one
MW: 344.315440 g/mol | MF: C18H16O7
159: CID: 5320848
CID5320848; 5-hydroxy-2-(4-hydroxy-3-sulfinatooxy-phenyl)-7-methoxy-4-oxo-3-sulfinatooxy-chromene
IUPAC: [2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxo-3-sulfinatooxychromen-2-yl)phenyl] sulfite
MW: 442.374000 g/mol | MF: C16H10O11S2-2
160: CID: 5400219
Oprea1_158180; Oprea1_711058; MolPort-001-836-336
IUPAC: 7,8-dihydroxy-2-methyl-3-phenoxychromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
161: CID: 5482937
Quercetin Analogs; AIDS114005; AIDS-114005
IUPAC: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] acetate
MW: 344.272380 g/mol | MF: C17H12O8
162: CID: 5492759
Potassium quercetin phosphate; CID5492759; LS-39610
IUPAC: potassium; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; hydrogen phosphate
MW: 437.313301 g/mol | MF: C15H11KO11P-
163: CID: 6105183
Oprea1_065446; Oprea1_827089; CID6105183
IUPAC: 7,8-dihydroxy-3-phenoxychromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
164: CID: 6481478
AIDS337573; MolPort-000-165-393; AIDS-337573
IUPAC: 5,6,7-trihydroxy-3-methoxy-2-(4-methoxyphenyl)chromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
165: CID: 9818879
CHEBI:303768; CID9818879; 2-(3,4-Dihydroxy-phenyl)-7-hydroxy-3-(2-hydroxy-ethoxy)-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(2-hydroxyethoxy)chromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
166: CID: 10473561
CID10473561; [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chromen-3-yl] Propanoate
IUPAC: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] propanoate
MW: 358.298960 g/mol | MF: C18H14O8
167: CID: 10807373
LMPK12111581; CID10807373; 3-hydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-7-methoxy-chromen-4-one
IUPAC: 3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxychromen-4-one
MW: 344.315440 g/mol | MF: C18H16O7
168: CID: 11834044
LMPK12112862; CID11834044; 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-methoxy-chromen-4-one
IUPAC: 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
169: CID: 13942543
CHEBI:405386; LMPK12112755; 2-(4-Hydroxy-3-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one
IUPAC: 2-(4-hydroxy-3-methoxyphenyl)-3,5,7-trimethoxychromen-4-one
MW: 358.342020 g/mol | MF: C19H18O7
170: CID: 14079475
LMPK12111600
IUPAC: 3,7-dihydroxy-8-methoxy-2-phenylchromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
171: CID: 14162697
CHEBI:405173; LMPK12112753; 7-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3,5-dimethoxy-chromen-4-one
IUPAC: 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,5-dimethoxychromen-4-one
MW: 344.315440 g/mol | MF: C18H16O7
172: CID: 18372853
IUPAC: 2-(3,4-dihydroxyphenyl)-3,8-dihydroxy-7-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
173: CID: 19890110
IUPAC: 3-hydroxy-2-(2-hydroxy-3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one
MW: 374.341420 g/mol | MF: C19H18O8
174: CID: 20159736
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(2-hydroxyethoxy)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
175: CID: 20833257
IUPAC: [2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] dihydrogen phosphate
MW: 382.215601 g/mol | MF: C15H11O10P
176: CID: 20981198
IUPAC: potassium 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one phosphate
MW: 436.305361 g/mol | MF: C15H10KO11P-2
177: CID: 22138197
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(2,2,2-trihydroxyethoxy)chromen-4-one
MW: 378.287060 g/mol | MF: C17H14O10
178: CID: 25183346
IUPAC: [2-hydroxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] dihydrogen phosphate
MW: 382.215601 g/mol | MF: C15H11O10P
179: CID: 44258703
LMPK12111607
IUPAC: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-8-methoxychromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
180: CID: 44258706
LMPK12111610
IUPAC: 3,7,8-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
MW: 316.262280 g/mol | MF: C16H12O7
181: CID: 44259678
LMPK12112722
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-6-methylchromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
182: CID: 44259679
LMPK12112723
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-8-methylchromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
183: CID: 44594804
IUPAC: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] dihydrogen phosphate
MW: 382.215601 g/mol | MF: C15H11O10P
184: CID: 5281953
Syringetin; 3’,5’-O-Dimethylmyricetin; CHEBI:18215
IUPAC: 3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
185: CID: 5282154
Laricitrin; 3’-O-Methylmyricetin; LMPK12112482
IUPAC: 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxychromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
186: CID: 5315126
Uralenol; CHEBI:288124; LMPK12112286
IUPAC: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxychromen-4-one
MW: 370.352720 g/mol | MF: C20H18O7
187: CID: 10343070
Broussonol E; CHEBI:565773; LMPK12112289
IUPAC: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
MW: 438.469740 g/mol | MF: C25H26O7
188: CID: 10359384
mearnsetin; CHEBI:583367; LMPK12112506
IUPAC: 2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxychromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
189: CID: 10365850
Broussonol D; CHEBI:565772; LMPK12112290
IUPAC: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
MW: 438.469740 g/mol | MF: C25H26O7
190: CID: 12314325
LMPK12112469
IUPAC: 3,5,7-trihydroxy-6-methyl-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 332.261680 g/mol | MF: C16H12O8
191: CID: 15559735
LMPK12113272
IUPAC: 3,5,7,8-tetrahydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 334.234500 g/mol | MF: C15H10O9
192: CID: 21676176
quercetin 3, 7, 4-trisulphate; quercetin 3, 7, 4’-trisulphate; CPD-10893
IUPAC: [2-hydroxy-4-(5-hydroxy-4-oxo-3,7-disulfonatooxychromen-2-yl)phenyl] sulfate
MW: 539.401480 g/mol | MF: C15H7O16S3-3
193: CID: 21676177
Quercetin 3,3’,7-trissulfate; QUERCETIN-337-TRISSULFATE
IUPAC: [2-hydroxy-5-(5-hydroxy-4-oxo-3,7-disulfonatooxychromen-2-yl)phenyl] sulfate
MW: 539.401480 g/mol | MF: C15H7O16S3-3
194: CID: 22507435
IUPAC: 3,5,7-trimethoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
MW: 360.314840 g/mol | MF: C18H16O8
195: CID: 25202456
Syringetin
IUPAC: 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-oxochromen-3-olate
MW: 345.280320 g/mol | MF: C17H13O8-
196: CID: 25203006
Laricitrin; CPD-8605
IUPAC: 2-hydroxy-6-methoxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenolate
MW: 331.253740 g/mol | MF: C16H11O8-
197: CID: 44259511
LMPK12112509
IUPAC: 3,5,7-trihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)chromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
198: CID: 44259638
LMPK12112666
IUPAC: 2-(3,5-dihydroxy-4-methoxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one
MW: 346.288260 g/mol | MF: C17H14O8
199: CID: 96506
Nortangeretin; MLS000736839; CHEBI:493043
IUPAC: 5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
Tested in BioAssays: All: 182, Active: 17
200: CID: 797370
Oprea1_264669; Oprea1_552685; MolPort-001-831-555
IUPAC: 2-phenoxy-1-(2,3,4-trihydroxyphenyl)ethanone
MW: 260.242080 g/mol | MF: C14H12O5
201: CID: 5280666
Chrysoeriol; Chryseriol; 3’-Methoxyapigenin
IUPAC: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
Tested in BioAssays: All: 261, Active: 6
202: CID: 5281612
Diosmetin; 4’-Methylluteolin; Luteolin 4’-methyl ether
IUPAC: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
Tested in BioAssays: All: 24, Active: 2
203: CID: 5281648
Hypolaetin; 8-Hydroxyluteolin; CHEBI:5837
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7,8-trihydroxychromen-4-one
MW: 302.235700 g/mol | MF: C15H10O7
204: CID: 5281665
Isoscutellarein; 8-Hydroxyapigenin; LMPK12111361
IUPAC: 5,7,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
205: CID: 5281674
Norwogonin; nor-wogonin; 5,7,8-Trihydroxyflavone
IUPAC: 5,7,8-trihydroxy-2-phenylchromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
Tested in BioAssays: All: 5, Active: 1
206: CID: 5320496
Pilloin; Luteolin 7,4’-dimethyl ether; CHEBI:583719
IUPAC: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
207: CID: 5464381
Velutin; Flavonoid; Luteolin 7,3’-dimethyl ether
IUPAC: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
208: CID: 5487855
sec-Butyl benzoate; 3’,4’-Dimethoxyquercetin; LMPK12112411
IUPAC: 2-(3,4-dimethoxyphenyl)-3,5,7-trihydroxychromen-4-one
MW: 330.288860 g/mol | MF: C17H14O7
209: CID: 10357421
CID10357421; 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methyl-chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methylchromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
210: CID: 11474580
CID11474580; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3-methylbut-2-enoxymethyl)chromen-4-one
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3-methylbut-2-enoxymethyl)chromen-4-one
MW: 384.379300 g/mol | MF: C21H20O7
211: CID: 13964547
CHEBI:405387; LMPK12110968; 7-Hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-5-methoxy-chromen-4-one
IUPAC: 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-5-methoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
212: CID: 13964549
Chrysoeriol 5-methyl ether; LMPK12110967
IUPAC: 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-methoxychromen-4-one
MW: 314.289460 g/mol | MF: C17H14O6
213: CID: 14016780
LMPK12110734
IUPAC: [2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl] hydrogen sulfate
MW: 366.299500 g/mol | MF: C15H10O9S
214: CID: 15293760
LMPK12110728
IUPAC: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methylchromen-4-one
MW: 300.262880 g/mol | MF: C16H12O6
215: CID: 21725619
IUPAC: [2-hydroxy-4-(5-hydroxy-4-oxo-7-sulfonatooxychromen-2-yl)phenyl] sulfate
MW: 444.346820 g/mol | MF: C15H8O12S2-2
216: CID: 44258151
LMPK12110735
IUPAC: [5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl] hydrogen sulfate
MW: 366.299500 g/mol | MF: C15H10O9S
217: CID: 44258152
LMPK12110736
IUPAC: [4-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl] hydrogen sulfate
MW: 366.299500 g/mol | MF: C15H10O9S
218: CID: 44608109
IUPAC: 7-butoxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
MW: 342.342620 g/mol | MF: C19H18O6
219: CID: 44610310
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-octoxychromen-4-one
MW: 398.448940 g/mol | MF: C23H26O6
220: CID: 44610311
IUPAC: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-propoxychromen-4-one
MW: 328.316040 g/mol | MF: C18H16O6
221: CID: 44610312
IUPAC: 5-decoxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
MW: 426.502100 g/mol | MF: C25H30O6
222: CID: 44610313
IUPAC: 2-(3,4-dihydroxyphenyl)-5-hexoxy-7-hydroxychromen-4-one
MW: 370.395780 g/mol | MF: C21H22O6
223: CID: 44610474
IUPAC: 5-butoxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
MW: 342.342620 g/mol | MF: C19H18O6
224: CID: 1880
7,8-dihydroxyflavone; FLAVONE; 7,8-Dihydroxy-flavone
IUPAC: 7,8-dihydroxy-2-phenylchromen-4-one
MW: 254.237500 g/mol | MF: C15H10O4
Tested in BioAssays: All: 92, Active: 8
225: CID: 676309
TNP00055; CHEBI:490243; CID676309
IUPAC: 7,8-dihydroxy-2-(2-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
Tested in BioAssays: All: 80, Active: 18
226: CID: 688853
7,8,4-trihydroxyflavone; CHEBI:246131; ZINC00057915
IUPAC: 7,8-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
227: CID: 9814421
CID9814421; 2-(2,4-dihydroxyphenyl)-7,8-dihydroxy-chromen-4-one
IUPAC: 2-(2,4-dihydroxyphenyl)-7,8-dihydroxychromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
228: CID: 18778789
IUPAC: (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxychromen-4-one
MW: 284.263480 g/mol | MF: C16H12O5
229: CID: 17840570
IUPAC: (3,5,6-trihydroxy-2-phenylchromen-4-ylidene)oxidanium
MW: 271.244840 g/mol | MF: C15H11O5+
230: CID: 17840571
IUPAC: 3,5,6-trihydroxy-2-phenylchromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
231: CID: 23064865
IUPAC: 2-(2,3,4,6-tetrahydroxyphenyl)chromen-4-one
MW: 286.236300 g/mol | MF: C15H10O6
232: CID: 5393165
ZINC00057845; CID5393165
IUPAC: 3,7-dihydroxy-2-(3-hydroxyphenyl)chromen-4-one
MW: 270.236900 g/mol | MF: C15H10O5
233: CID: 20977459
IUPAC: [3,5,7-trihydroxy-2-(3-hydroxyphenyl)chromen-4-ylidene]oxidanium chloride
MW: 322.697240 g/mol | MF: C15H11ClO6
本明細書において、「イオノマイシン」(Ionomycin)とは、PubChemから引用すると、以下の特性を有する化合物であり、化学式(3)で表される。
Compound ID 44134784
IUPAC: calcium 19,21-dihydroxy-22-[5-[5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
Molecular Weight 747.0671 [g/mol]
Molecular Formula C41H70CaO9
H-Bond Donor 3
H-Bond Acceptor 9
1: CID: 6446270
Ionomycin, calcium salt; MolPort-003-983-599; CID6446270
IUPAC: calcium (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-19,21-dihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 747.067100 g/mol | MF: C41H70CaO9
2: CID: 24839624
LS-84163
IUPAC: calcium; (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 749.082980 g/mol | MF: C41H72CaO9
3: CID: 42602091
IUPAC: calcium (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2R,5R)-5-[(2S,5R)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 749.082980 g/mol | MF: C41H72CaO9+2
4: CID: 44120021
BII0123
IUPAC: calcium (4S,6R,8R,10Z,12S,14S,16E,18S,19S,20R,21S)-19,21-dihydroxy-22-[(2R,5S)-5-[(2S,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 747.067100 g/mol | MF: C41H70CaO9
5: CID: 44134784
ionomycin; 56092-82-1
IUPAC: calcium 19,21-dihydroxy-22-[5-[5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 747.067100 g/mol | MF: C41H70CaO9
Ionophores more
6: CID: 3733
ionomycin; CID3733; 56092-81-0
IUPAC: 11,19,21-trihydroxy-22-[5-[5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
7: CID: 3611369
CID3611369; CID 3611369
IUPAC: 19,21-dihydroxy-22-[5-[5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 706.989100 g/mol | MF: C41H70O9-2
8: CID: 6434517
ionomycin; CID6434517; LS-84162
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(5S)-5-[(5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
9: CID: 6711156
ionomycin; MolMap_000033; CID6711156
IUPAC: (4R,6S,8S,12R,14R,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2R,5R)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
10: CID: 6912226
ionomycin; CHEBI:566812; HSCI1_000207
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
11: CID: 9831149
CID9831149; CID 9831149
IUPAC: (10Z,16E)-11,19-dihydroxy-20-[5-[5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,4,6,8,12,14,18-heptamethyl-9-oxoicosa-10,16-dienoic acid
MW: 664.952420 g/mol | MF: C39H68O8
12: CID: 10372625
ionomycin; CID10372625
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2R,5R)-5-[(2S,5R)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
13: CID: 12967103
NCGC00162460-01
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Tested in BioAssays: All: 34, Active: 1
14: CID: 16219538
I9657_SIGMA; Ionomycin from Streptomyces conglobatus
IUPAC: (4S,6R,8R,10Z,12S,14S,16E,18S,19S,20R,21S)-11,19,21-trihydroxy-22-[(5S)-5-[(5S)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
15: CID: 16759612
NCGC00162463-01
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-19,21-dihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 706.989100 g/mol | MF: C41H70O9-2
Tested in BioAssays: All: 34, Active: 0
16: CID: 24742080
nchembio.79-comp37; 4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-Trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-[(2S,2’R,5S,5’S)-octahydro-5’-[(1R)-1-hydroxyethyl]-2,5’-dimethyl[2,2’-bifuran]-5-yl]-9-oxo-10,16-docosadienoic acid calcium salt
IUPAC: (4S,6R,8R,10Z,12S,14S,16E,18S,19S,20R,21S)-19,21-dihydroxy-22-[(5S)-5-[(5S)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoate
MW: 706.989100 g/mol | MF: C41H70O9-2
17: CID: 25134244
ionomycin; nchembio.146-comp9
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(5S)-5-[(5S)-5-(1-hydroxyethyl)-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
Ionophores more
18: CID: 44120022
IUPAC: (4S,6R,8R,10Z,12S,14S,16E,18S,19S,20R,21S)-11,19,21-trihydroxy-22-[(2R,5S)-5-[(2S,5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
19: CID: 44120023
BII0421
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18S,19S,20R,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2S,5R)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
20: CID: 44560066
CHEBI:546782; (3R,5S,7S,9Z,11R,13R,15E,17R,18R,19S,20S)-1-carboxy-18,20-dihydroxy-21-((2S,5S)-5-((2R,5S)-5-((S)-1-hydroxyethyl)-5-methyl-tetrahydrofuran-2-yl)-5-methyl-tetrahydrofuran-2-yl)-3,5,7,11,13,17,19-heptamethyl-8-oxohenicosa-9,15-dien-10-olate
IUPAC: (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(2S,5S)-5-[(2R,5S)-5-[(1S)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
MW: 709.004980 g/mol | MF: C41H72O9
本明細書において、「PKF115−584」とは、非特許文献6(Maina Lepourcelet et al., “Small-molecule antagonists of the oncogenic Tcf/β-catenin protein complex”, CANCER CELL, JANUARY 2004, VOL. 5, 91-102)から引用すると、以下の特性を有する化合物であり、化学式(4)で表される。
本実施形態に係るから肝細胞を生産する方法は、間葉系幹細胞を上記の分化誘導剤で処理する工程を含む、生産方法である。この方法によれば、Wnt/β−カテニン経路を抑制する有機低分子量化合物を用いるので、蛋白製剤や核酸製剤に比べ安定性・安全性などの面で優れており、間葉系幹細胞から肝細胞への分化誘導を効率よく安全に行うことができる。
このようにして分化誘導された肝細胞は、肝細胞移植などの移植医療、薬の薬効や副作用を評価する創薬などの用途に好適に用いることができる。また、この肝細胞は、Wnt/β−カテニン経路を抑制する有機低分子量化合物を用いて間葉系幹細胞から分化誘導されるので、蛋白製剤や核酸製剤を用いて分化誘導される場合に比べ製造時の安定性・安全性などの面で優れている。
Luciferase発現ベクター安定導入株の構築(UE7T−13)
図1は、β−catenin/TCF4/ルシフェラーゼレポーター遺伝子を安定発現するヒト間葉系幹細胞の樹立方法について説明するための概念図である。図1に示すように、Luciferase発現ベクターを用いてpTCF4−CMVpro−GL4.20プラスミドを構築した。TCF4−CMVpro−GL4.20プラスミドは、3回繰り返しのTCF4配列CCTTTGATCをCMVプロモーターの上流に含み、luciferaseを発現する。また、pCMVpro−GL4.20プラスミドをコントロールとして構築した。得られたプラスミドをそれぞれ線状化し、UE7T−13にエレクトロポレーションによって導入し、培地中に加えたPuromycin(0.25μg/ml)によって選別した。Puromycin耐性の細胞はクローン化し、luciferaseアッセイに用いることにした。
ヘキサクロロフェンによる分化誘導
本発明者らは、骨髄由来細胞(UE7T−13細胞)をヘキサクロロフェンで処理した場合について(1)増殖能(毒性)の検討、(2)Wnt/β−catenin経路抑制能の検討、(3)肝細胞分化能の検討を検討項目とした。
ヒト間葉系幹細胞株UE7T−13を細胞密度が9.0x103cells/cm2になるように96well plate(底面積:0.3cm2)に播種し、10%ウシ胎児血清(FBS,JRH Biosciences,INC)、100U/ml penicillin、100ug/ml streptomycin(Nacalai Tesque)を含むDulbecco’s Modified Eagle’s Medium (DMEM,ニッスイ)にて培養した。この時点をday0とする。翌日(day1)、ヘキサクロロフェンなどの低分子化合物を含むDMEMにメディウムチェンジした。以降、day2、day4、day8にTetraColor one(生化学工業)を用いて測定を行い、UE7T−13の細胞増殖への影響を検討した。培養液に含まれるDMSOは、終濃度が0.1%となるようにした。
24well plateにLuciferase発現ベクター安定導入株を播種し、37℃で培養した。翌日、MTTアッセイの結果から細胞増殖に影響の無い濃度のヘキサクロロフェンなどの低分子化合物を含むメディウムに交換し、37℃で培養した。その後、1,4,8日後にluciferase活性をLuciferase Assay System(Promega)を使用し、556nmの波長を蛍光プレートリーダー(ARVIO)で測定した。
(3−1) 分化誘導(UE7T−13)
6well plateに細胞密度が9.0x103cells/cm2になるように播種し、37℃で24時間培養した。24時間後に、Luciferaseアッセイにより検討した濃度のヘキサクロロフェンなどの低分子化合物を含むメディウムに交換した。以降、週に2回培地交換し、週に1回継代して細胞数を9.0x103cells/cm2に調整した。誘導開始から8、16、24日目にTotal RNAを回収した。
Total RNAは、TRIzol試薬で抽出した。抽出後、DNAを完全に除くため、Deoxyribonucleaseを加えて37℃で1時間インキュベートした。逆転写反応には、SuperScript First−Stand Synthesis System for RT−PCR(Invitrogen)を使用し、1μgのRNAをOligo dT PrimerにてcDNAへ変換した。PCRには、cDNAを5倍希釈し、そのうち1μlを使用した。PCR反応には、Taq DNA polymerase,recombinat(Invitrogen)を使用した。ヒトアルブミンのプライマーは、5’−TTGGAAAAATCCCACTGCAT−3’(配列番号:1)と5’−CTCCAAGCTGCTCAAAAAGC−3’(配列番号:2)を用いた。PCR反応は、95℃2分で1サイクル、95℃30秒、58℃30秒、72℃30秒で35サイクル施行した。内部対照としてヒトglyceradehyde 3−phosphate dehydrogenase(GAPDH)を用いた。GAPDHプライマーは、5’−GTCTTCTCCACCATGGAGAAGGCT−3’(配列番号:3)と5’−CATGCCAGTGAGCTTCCCGTTCA−3’(配列番号:4)を用いた。PCR反応は、95℃2分で1サイクル、95℃30秒、60℃30秒、72℃30秒で20サイクル施行した。PCR産物は、エチジウムブロマイドの入った2%アガロースゲルで30分間電気泳動し、トランスイルミネ―ターを用いて写真を撮った。
6well plateに70% EtOHで滅菌したカバーガラス(22x22mm,MATSUNAMI)を入れ、その上に細胞を播種し、ヘキサクロロフェンなどの低分子化合物を含む培地で培養した。培養開始から8,16,24日後にPBSで2回洗浄した後、4%パラホルムアルデヒド/PBSで細胞を20分間処理してカバーガラスに固定した。その後、0.2% Triton X−100で10分間透過処理した。3% BSA/PBSで30分間処理してブロッキングした。一次抗体としてanti−albumin antibody, anti−C/EBP antibody, anti−AFP antibody, anti−CYP1A1 antibodyを用い、4℃で一晩インキュベートした。次に、二次抗体としてAlexa Fluoro 488 goat anti−mouse antibody、Alexa Fluoro 594 goat anti−rabbit antibodyを用い、室温で1時間インキュベートした。核染色にDAPIを用いた。カバーガラスをPBSで希釈した50% glycerolで封入し、共焦点レーザー顕微鏡下で観察した。0.1% DMSOで培養した細胞をコントロールとした。
6well plateに70% EtOHで滅菌したカバーガラス(22x22mm,MATSUNAMI)を入れ、その上に細胞を播種し、ヘキサクロロフェンなどの低分子化合物を含む培地で培養した。培養開始から8,16,24日後にPBSで2回洗浄した後、4%パラホルムアルデヒド/PBSで細胞を20分間処理してカバーガラスに固定した。陰性対照として、10mg/mlのα−アミラーゼ(10mg/ml,0.1M リン酸緩衝液,pH6.8)で1時間、37℃でインキュベートしてグリコーゲンを消化した。1%過ヨウ素酸水溶液で10分間酸化処理した後、Schiff試薬で15分間処理してグリコーゲンを染色し、亜硫酸水溶液で3回、蒸留水で3回洗浄した。Mayer’s hematoxylinで核染色した後、カバーガラスをPBSで希釈した50% glycerolで封入し、光学顕微鏡下で観察した。0.1% DMSOで培養した細胞をコントロールとした。
細胞を24well plateに播種し、ヘキサクロロフェンなどの低分子化合物を含む培地で培養した。メディウムに塩化アンモニウム(終濃度5mM)を加え、48,72,96時間培養後にメディウム中の尿素量をQuantiChrom Urea Assay Kit(BioAssay Systems)を使用し、520nmの波長を蛍光プレートリーダー(TECAN)を用いて測定した。
ケルセチンによる分化誘導
本発明者らは、2種類の細胞(骨髄由来細胞(UE7T−13細胞)、臍帯血由来細胞(UCBTERT−21細胞))をケルセチンで処理した場合について(1)増殖能(毒性)の検討、(2)Wnt/β−catenin経路抑制能の検討、(3)肝細胞分化能の検討を検討項目とした。なお、実施例2のヘキサクロロフェンでの実験と同様の点については説明の煩雑を避けるために省略している。
(1−1)骨髄由来細胞(UE7T−13細胞)の場合
図10は、ケルセチンによるWnt/β−catenin活性への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。ケルセチンで処理した場合にも骨髄由来細胞(UE7T−13細胞)の増殖が有意に抑制されたが、増殖能自体は抑制された状態ではあるが維持されていた。すなわち、ケルセチンによる骨髄由来細胞(UE7T−13細胞)への細胞毒性は十分に低く、分化誘導剤として使用可能な水準であることが判明した。特に、5μMでのケルセチンによる骨髄由来細胞(UE7T−13細胞)への細胞毒性は非常に低いことが判明した。
ヒト臍帯血由来間葉系幹細胞株UCBTERT−21を細胞密度が2.0x103cells/cm2になるように96well plate(底面積:0.3cm2)に播種し、10%ウシ胎児血清(FBS,JRH Biosciences,INC)を含むMSCGM(三光純薬)にて培養した。この時点をday0とする。翌日(day1)、ケルセチンなどの低分子化合物を含むDMEMにメディウムチェンジした。以降、day2、day4、day8にTetraColor one(生化学工業)を用いて測定を行い、UCBTERT−21の細胞増殖への影響を検討した。培養液に含まれるDMSOは、終濃度が0.1%となるようにした。
(2−1)骨髄由来細胞(UE7T−13細胞)の場合
図10は、ケルセチンによるWnt/β−catenin活性への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。TCF4−CMVルシフェラーゼプラスミドによるレポーターアッセイにより、1μMでのケルセチンによる骨髄由来細胞(UE7T−13細胞)を処理するとケルセチン処理8日後にはWnt/β−cateninシグナルは有意に抑制されていることを確認した。
24well plateにUCBTERT−21を細胞密度が2.0x103cells/cm2になるように播種し、37℃で24時間培養した。翌日、MTTアッセイの結果から細胞増殖に影響の無い濃度のケルセチンなどの低分子化合物を含むメディウムに交換し、37℃で培養した。その後、1,4,8日後にレポーター遺伝子をトランスフェクションした。トランスフェクションにはFugene6 Transfection Rreagent(Roche)を用いた。さらに24時間後に、luciferase活性をDual Luciferase Assay System(Promega)を使用してルシフェラーゼ活性を測定した。
(3−1)骨髄由来細胞(UE7T−13細胞)の場合
図11は、ケルセチンによる肝細胞分化誘導能(UE7T−13)について説明するための電気泳動写真である。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。ケルセチンによる処理の結果、肝細胞への分化誘導の代表的なマーカーであるアルブミンの発現量がいずれもコントロールにくらべて明らかに増大していた。
(3−2)分化誘導(UCBTERT−21)
6well plateに細胞密度が2.0x103cells/cm2になるように播種し、37℃で24時間培養した。24時間後に、Luciferaseアッセイにより検討した濃度のケルセチンなどの低分子化合物を含むメディウムに交換した。以降、週に2回培地交換し、週に1回継代して細胞数を2.0x103cells/cm2に調整した。誘導開始から8、16、24日目にTotal RNAを回収した。
Total RNAは、RNeasy Micro Kit(QIAGEN)を用いて抽出した。逆転写反応には、SuperScript First−Stand Synthesis System for RT−PCR(Invitrogen)を使用し、0.5μgのRNAをOligo dT PrimerにてcDNAへ変換した。PCRには、cDNAを5倍希釈し、そのうち1μlを使用した。PCR反応には、Taq DNA polymerase,recombinat(Invitrogen)を使用した。ヒトアルブミンのプライマーは、5’−TTGGAAAAATCCCACTGCAT−3’(配列番号:5)と5’−CTCCAAGCTGCTCAAAAAGC−3’(配列番号:6)を用いた。PCR反応は、95℃2分で1サイクル、95℃30秒、58℃30秒、72℃30秒で35サイクル施行した。内部対照としてヒトglyceradehyde 3−phosphate dehydrogenase(GAPDH)を用いた。GAPDHプライマーは、5’−GTCTTCTCCACCATGGAGAAGGCT−3’(配列番号:7)と5’−CATGCCAGTGAGCTTCCCGTTCA−3’(配列番号:8)を用いた。PCR反応は、95℃2分で1サイクル、95℃30秒、60℃30秒、72℃30秒で20サイクル施行した。PCR産物は、エチジウムブロマイドの入った2%アガロースゲルで30分間電気泳動し、トランスイルミネ―ターを用いて写真を撮った。
図15は、ケルセチンによる肝細胞分化誘導(day24)について説明するための蛍光顕微鏡写真である。なお、実験方法はUE7T−13およびUCBTERT−21で共通であり、実施例2で既に説明したので繰り返さず結果のみ説明する。ケルセチンによる肝細胞分化誘導を行った結果、ケルセチンによる処理24日後には、肝細胞への分化誘導の代表的なマーカーであるアルブミン、C/EBPαなどのマーカーの発現量がいずれもネガティブコントロール(0.1%DMSO)にくらべて明らかに増大して、ポジティブコントロール(肝癌細胞のHuH7)に近い量になっていた。図16は、ケルセチンによる肝細胞分化誘導について説明するためのグラフである。図15の結果を定量化して示すと、ケルセチンによる処理24日後には、肝細胞への分化誘導の代表的なマーカーであるアルブミン、C/EBPαなどのマーカーの発現量がいずれもネガティブコントロール(0.1%DMSO)にくらべて明らかに増大していた。
図17は、ケロセチンによる分化誘導サンプルの尿素合成能(day24)について説明するためのグラフである。なお、実験方法はUE7T−13およびUCBTERT−21で共通であり、実施例2で既に説明したので繰り返さず結果のみ説明する。ケロセチンによる肝細胞分化誘導能(尿素合成能測定)を24日間行った結果、尿素合成時間が48時間、ケロセチン投与量が5μMの条件では、細胞の尿素合成能がネガティブコントロール(0.1%DMSO)にくらべて有意に増大して、ポジティブコントロール(肝癌細胞のHepG2)と同等になっていることがわかる。これは、単に肝細胞マーカーを有するのみでなく、機能性肝機能としての能力をもつことを示している。
イオノマイシンによる分化誘導
本発明者らは、骨髄由来細胞(UE7T−13細胞)をイオノマイシンで処理した場合について(1)増殖能(毒性)の検討、(2)Wnt/β−catenin経路抑制能の検討、(3)肝細胞分化能の検討を検討項目とした。なお、実施例2のヘキサクロロフェンまたは実施例3のケルセチンでの実験と同様の点については説明の煩雑を避けるために省略している。
図18は、イオノマイシンによる細胞増殖能への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。イオノマイシンで処理した場合にも骨髄由来細胞(UE7T−13細胞)の増殖が有意に抑制されたが、増殖能自体は抑制された状態ではあるが維持されていた。すなわち、イオノマイシンによる骨髄由来細胞(UE7T−13細胞)への細胞毒性は十分に低く、分化誘導剤として使用可能な水準であることが判明した。特に、0.1μMでのイオノマイシンによる骨髄由来細胞(UE7T−13細胞)への細胞毒性は非常に低いことが判明した。
図18は、イオノマイシンによるWnt/β−catenin活性への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。TCF4−CMVルシフェラーゼプラスミドによるレポーターアッセイにより、0.01μMでのイオノマイシンによる骨髄由来細胞(UE7T−13細胞)を処理するとイオノマイシン処理8日後にはWnt/β−cateninシグナルは有意に抑制されていることを確認した。
図11は、イオノマイシンによる肝細胞分化誘導能(UE7T−13)について説明するための電気泳動写真である。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。イオノマイシンによる処理の結果、肝細胞への分化誘導の代表的なマーカーであるアルブミンの発現量がいずれもコントロールにくらべて明らかに増大していた。
PKF−115−584による分化誘導
本発明者らは、骨髄由来細胞(UE7T−13細胞)をPKF−115−584で処理した場合について(1)増殖能(毒性)の検討、(2)Wnt/β−catenin経路抑制能の検討、(3)肝細胞分化能の検討を検討項目とした。なお、実施例2のヘキサクロロフェン、実施例3のケルセチンまたは実施例4のイオノマイシンでの実験と同様の点については説明の煩雑を避けるために省略している。
図19は、PKF−115−584による増殖能への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。PKF−115−584で処理した場合にも骨髄由来細胞(UE7T−13細胞)の増殖が有意に抑制されたが、増殖能自体は抑制された状態ではあるが維持されていた。すなわち、PKF−115−584による骨髄由来細胞(UE7T−13細胞)への細胞毒性は十分に低く、分化誘導剤として使用可能な水準であることが判明した。特に、5nMでのPKF−115−584による骨髄由来細胞(UE7T−13細胞)への細胞毒性は非常に低いことが判明した。
図19は、PKF−115−584によるWnt/β−catenin活性への影響(UE7T−13)について説明するためのグラフである。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。TCF4−CMVルシフェラーゼプラスミドによるレポーターアッセイにより、3nMでのPKF−115−584による骨髄由来細胞(UE7T−13細胞)を処理するとPKF−115−584処理8日後にはWnt/β−cateninシグナルは有意に抑制されていることを確認した。
図20は、PKF−115−584による肝細胞分化誘導能(UE7T−13)について説明するための電気泳動写真である。なお、実験方法は実施例2で既に説明したので繰り返さず結果のみ説明する。PKF−115−584による処理の結果、肝細胞への分化誘導の代表的なマーカーであるアルブミン、AFPの発現量がいずれもコントロールにくらべて明らかに増大していた。
上記の実施例の実験結果から、本発明者らは、Wnt/β−カテニン経路を抑制する有機低分子量化合物を用いてヒト間葉系幹細胞を機能性肝細胞へ分化誘導可能であることを明らかにした。つまり、肝再生医療の実現化に向けて、間葉系幹細胞は肝再生医療の細胞ソースとして有用であり、さらに分化誘導時に有機低分子量化合物によるWnt/β−cateninシグナルの抑制が有効であることを明らかにした。これらは、真に臨床応用可能な肝再生医療の開発をしていく上で重要な知見であり、今後さらなる研究の進展が必要である。
Claims (13)
- 間葉系幹細胞の肝細胞への分化誘導剤であって、
Wnt/β−カテニン経路を抑制する有機低分子量化合物を含む、分化誘導剤。 - 請求項1記載の分化誘導剤において、
前記有機低分子量化合物の分子量が1000以下である、分化誘導剤。 - 請求項1または2記載の分化誘導剤において、
前記有機低分子量化合物が、ペプチドおよびヌクレオチドを除く、分化誘導剤。 - 請求項1乃至3いずれかに記載の分化誘導剤において、
前記有機低分子量化合物が、ヘキサクロロフェン、ケルセチン、イオノマイシン、PKF115−584からなる群から選ばれる1種以上の化合物またはその類縁体である、分化誘導剤。 - 請求項4記載の分化誘導剤において、
前記有機低分子量化合物が、式(1)〜式(4)に示す化合物群から選ばれる1種以上の有機低分子量化合物またはその類縁体である、分化誘導剤。
- 請求項1乃至5いずれかに記載の分化誘導剤において、
前記間葉系幹細胞が、骨髄由来細胞または臍帯血由来細胞である、分化誘導剤。 - 請求項1乃至6いずれかに記載の分化誘導剤において、
前記間葉系幹細胞におけるアルブミン、C/EBPα、CYPA1/A2およびAFPからなる群から選ばれる1種以上の蛋白質の発現を誘導する、分化誘導剤。 - 請求項1乃至7いずれかに記載の分化誘導剤において、
前記間葉系幹細胞におけるグリコーゲン生産能または尿素合成能を増強する、分化誘導剤。 - 間葉系幹細胞から肝細胞を生産する方法であって、
間葉系幹細胞を請求項1乃至8いずれかに記載の分化誘導剤で処理する工程を含む、生産方法。 - 請求項9記載の生産方法において、
前記分化誘導剤で処理する工程が、前記間葉系幹細胞を前記分化誘導剤で8日以上処理する工程を含む、生産方法。 - 間葉系幹細胞から分化誘導された肝細胞であって、
間葉系幹細胞を請求項1乃至8いずれかに記載の分化誘導剤で処理してなる、肝細胞。 - 再生医療用の肝組織であって、
請求項11記載の肝細胞を含む、肝組織。 - 再生医療用の肝臓であって、
請求項11記載の肝細胞を含む、肝臓。
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