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Glycocholic Acid

AlkaPlorer ID: AK000977

Synonym: None

IUPAC Name: 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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]3C[C@H](O)[C@]12C

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InChI: InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1

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InChIKey: RFDAIACWWDREDC-FRVQLJSFSA-N

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Reference

PubChem CID: 10140

SuperNatural Ⅲ: SN0323649-06

NPASS: NPC319029

Source

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

Properties Information

Molecule Weight: 465.6310000000003

TPSA？: 130.58

MolLogP？: 3.4052000000000024

Number of H-Donors: 5

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli K-12 Beta-lactamase AmpC Potency 1412.5 nM None
Escherichia coli K-12 Beta-lactamase AmpC Potency 2818.4 nM None
Homo sapiens ATP-binding cassette sub-family C member 11 Activity 62.0 % 10.1124/mol.104.007138
Homo sapiens ATP-binding cassette sub-family C member 11 Activity nan None 10.1124/mol.104.007138
Homo sapiens Bile acid transporter Activity 44.0 % 10.1172/jci117091
Homo sapiens Bile acid transporter Activity nan None 10.1002/hep.510260641
Homo sapiens Bile salt export pump Activity 108.0 % 10.1016/j.bmc.2012.03.016
Homo sapiens Bile salt export pump Ki 11000.0 nM 10.1053/gast.2002.36591
Homo sapiens Bile salt export pump Km 11100.0 nM 10.1053/gast.2002.36587
Homo sapiens Chromobox protein homolog 1 Potency 79432.8 nM None
Homo sapiens Chromobox protein homolog 1 Potency 112201.8 nM None
Homo sapiens Geminin Potency 1258.9 nM None
Homo sapiens Geminin Potency 31622.8 nM None
Homo sapiens G-protein coupled bile acid receptor 1 EC50 13600.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 103.0 % 10.1021/jm7015864
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 5623.4 nM None
Homo sapiens Multidrug resistance associated protein Activity 10.4 % None
Homo sapiens Multidrug resistance associated protein Activity 30.0 % 10.1042/bj20021081
Homo sapiens Multidrug resistance associated protein Km 248000.0 nM None
Homo sapiens Multidrug resistance-associated protein 4 Activity 45.0 % 10.1053/jhep.2003.50331
Homo sapiens Multidrug resistance-associated protein 4 IC50 400000.0 nM 10.1042/bj20021886
Homo sapiens Multidrug resistance-associated protein 7 Activity 58.4 % 10.1124/mol.63.2.351
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity 24.0 % 10.1016/0016-5085(95)90588-x
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity 81.0 % 10.1016/0016-5085(95)90588-x
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity nan None 10.1053/gast.2001.21176
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1053/gast.2001.21176
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 66.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Activity nan None 10.1053/gast.2001.21176
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 29.0 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1C1 Activity nan None 10.1210/me.2001-0309
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition -9.8 % 10.1021/jm300212s
Mus musculus Bile salt export pump Km 19500.0 nM 10.1053/jhep.2001.24171
Mus musculus Ileal sodium/bile acid cotransporter Activity nan None 10.1093/oxfordjournals.jbchem.a022358
Mus musculus Sodium/bile acid cotransporter Activity nan None 10.1271/bbb.66.1116
Rattus norvegicus Bile acid transporter Activity nan None 10.1152/ajpgi.00352.2002
Rattus norvegicus Bile acid transporter Activity nan None None
Rattus norvegicus Bile acid transporter Km 27000.0 nM 10.1152/ajpgi.1998.274.2.g370
Rattus norvegicus Bile salt export pump Activity nan None 10.1016/s0016-5085(00)70224-1
Rattus norvegicus Canalicular multispecific organic anion transporter 2 Activity 0.0 % 10.1074/jbc.275.4.2905
Rattus norvegicus Canalicular multispecific organic anion transporter 2 Activity 13.9 % 10.1074/jbc.275.4.2905
Rattus norvegicus Canalicular multispecific organic anion transporter 2 Activity 16.0 % 10.1074/jbc.275.4.2905
Rattus norvegicus Canalicular multispecific organic anion transporter 2 Activity nan None 10.1074/jbc.275.4.2905
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 10.1016/0270-9139(94)90194-5
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Activity nan None 10.1016/s0005-2736(03)00080-4
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 1A1 Activity nan None None
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Km 54000.0 nM 10.1152/ajpgi.1999.276.4.g1037
Rattus norvegicus Solute carrier organic anion transporter family member 1A3 Activity nan None None
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 15400.0 nM 10.1152/ajpgi.2000.279.6.g1188
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Streptococcus Streptococcus EC50 150000.0 nM None
Streptococcus pyogenes serotype M1 Streptokinase A EC50 150000.0 nM None
Streptococcus sp. 'group A' Streptococcus sp. 'group A' EC50 150000.0 nM None
None ADMET Activity 0.877 % 10.1016/j.bmc.2010.07.030
None ADMET Activity 1.052 % 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
None Unchecked Potency 35481.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013245 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]3C[C@H](O)[C@]12C>>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]3C[C@H](O)[C@]12C.NCC(=O)O None
AKRT013253 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>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]3C[C@H](O)[C@]12C 53852
AKRT013254 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCC(=O)O)[C@@H]1CC[C@H]2[C@@H]3[C@H](OS(=O)(=O)O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@@H]3C[C@H](O)[C@]12C 67556
AKRT013255 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>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]3C[C@H](O)[C@@]21C enzymemap_1479
AKRT013256 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC(=O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O enzymemap_1631
AKRT013257 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O enzymemap_4806
AKRT013258 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O enzymemap_50056
AKRT013259 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O CHOLOYLGLYCINE-HYDROLASE-RXN
AKRT013260 C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>NCC(=O)O CHOLOYLGLYCINE-HYDROLASE-RXN
AKRT013335 C[C@H](CCC(=O)[32S])[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]3C[C@H](O)[C@]12C.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]3C[C@H](O)[C@]12C None
AKRT013349 C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O.NCC(=O)O>>C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O GLYCINE-N-CHOLOYLTRANSFERASE-RXN