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Glycochenodeoxycholic Acid

AlkaPlorer ID: AK033348

Synonym: None

IUPAC Name: 2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid

Structure

SMILES: C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

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InChI: InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1

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InChIKey: GHCZAUBVMUEKKP-XROMFQGDSA-N

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Reference

PubChem CID: 12310288

CAS: 64480-66-6

SuperNatural Ⅲ: SN0105607-06

NPASS: NPC270957

Source

Species Genus Family Order Class Phylum Kingdom Domain
Homo sapiens Homo Hominidae Primates Mammalia Chordata Metazoa Eukaryota

Properties Information

Molecule Weight: 449.6320000000004

TPSA？: 106.86

MolLogP？: 3.594100000000001

Number of H-Donors: 4

Number of H-Acceptors: 4

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Bile acid receptor FXR IC50 98400.0 nM 10.1021/acs.jmedchem.2c01394
Homo sapiens G-protein coupled bile acid receptor 1 EC50 33900.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 91.0 % 10.1021/jm7015864
Homo sapiens HEK-293T IC50 100000.0 nM 10.1021/acs.jmedchem.2c01394
Homo sapiens Ileal bile acid transporter Km 4100.0 nM 10.1152/ajpgi.1998.274.1.g157
Mus musculus Bile acid receptor Activity nan None 10.1021/acs.jmedchem.2c01394
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.2c01394
Rattus norvegicus Ileal sodium/bile acid cotransporter Activity nan None 10.1152/ajpgi.2000.279.6.g1188
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Activity nan None 10.1152/ajpgi.00352.2002
Rattus norvegicus Solute carrier organic anion transporter family member 1A5 Activity nan None 10.1152/ajpgi.2000.279.6.g1188
Rattus norvegicus Solute carrier organic anion transporter family member 1A5 Km 5300.0 nM 10.1152/ajpgi.2000.279.6.g1188
None ADMET Activity 1.038 % 10.1016/j.bmc.2010.07.030
None ADMET Activity 1.092 % 10.1016/j.bmc.2010.07.030
None ADMET CC50 nan None 10.1016/j.bmc.2010.07.030
None Unchecked Activity nan None 10.1152/ajpgi.00360.2003

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013239 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C(=O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_2603
AKRT013240 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_77017
AKRT013241 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C MNXR158091
AKRT013242 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>NCC(=O)O MNXR158091
AKRT013342 C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C.NCC(=O)O>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_31610