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Taurolithocholic Acid

AlkaPlorer ID: AK009630

Synonym: None

IUPAC Name: 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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]ethanesulfonic acid

Structure

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

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InChI: InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

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InChIKey: QBYUNVOYXHFVKC-GBURMNQMSA-N

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Reference

PubChem CID: 439763

CAS: 516-90-5

NPASS: NPC320479

Source

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

Properties Information

Molecule Weight: 483.7150000000004

TPSA？: 103.7

MolLogP？: 4.426500000000003

Number of H-Donors: 3

Number of H-Acceptors: 4

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cricetulus griseus CHO Activity nan None 10.1021/acs.jmedchem.9b00770
Homo sapiens ATP-binding cassette sub-family G member 2 Activity 20.0 % 10.1124/mol.64.3.610
Homo sapiens Bile acid receptor FXR Activity 5.29 % 10.1021/np8004453
Homo sapiens Bile acid receptor FXR Activity 98.4 % 10.1021/np8004453
Homo sapiens Bile acid transporter Activity 33.0 % 10.1172/jci117091
Homo sapiens Bile acid transporter Inhibition nan % 10.1021/acs.jmedchem.0c01484
Homo sapiens Bile salt export pump Activity nan None 10.1023/a:1023278211849
Homo sapiens Bile salt export pump IC50 189200.0 nM 10.1023/a:1023278211849
Homo sapiens Canalicular multispecific organic anion transporter 1 Activity 27.0 % 10.1021/jm7015683
Homo sapiens Canalicular multispecific organic anion transporter 1 Activity nan None 10.1152/ajpgi.00383.2001
Homo sapiens G-protein coupled bile acid receptor 1 Activity nan None 10.1021/jm500889f
Homo sapiens G-protein coupled bile acid receptor 1 Activity nan None 10.1021/jm501273r
Homo sapiens G-protein coupled bile acid receptor 1 EC50 290.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 EC50 330.0 nM 10.1021/acs.jmedchem.9b00770
Homo sapiens G-protein coupled bile acid receptor 1 EC50 847.0 nM 10.1021/acs.jmedchem.9b00770
Homo sapiens G-protein coupled bile acid receptor 1 EC50 1005.4 nM 10.1039/d0md00425a
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 80.0 % 10.1021/acs.jmedchem.9b00770
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 106.0 % 10.1021/jm7015864
Homo sapiens Multidrug resistance-associated protein 1 Activity 56.0 % 10.1016/s0005-2736(97)00003-5
Homo sapiens Multidrug resistance-associated protein 4 IC50 20000.0 nM 10.1042/bj20021886
Homo sapiens P-glycoprotein 1 Activity 40.0 % 10.1016/0270-9139(94)90150-3
Homo sapiens Phospholipase A2 group 1B Activity 40.0 % 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Activity 70.0 % 10.1021/np8004453
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 97.8 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 89.8 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 94.6 % 10.1021/jm300212s
Homo sapiens Vitamin D receptor EC50 150000.0 nM 10.1016/j.ejmech.2016.01.002
Homo sapiens Vitamin D receptor IC50 14500.0 nM 10.1016/j.ejmech.2016.01.002
Homo sapiens Vitamin D receptor IC50 50000.0 nM 10.1016/j.ejmech.2016.01.002
Mus musculus Ephrin type-A receptor 2 IC50 72000.0 nM 10.1021/acs.jmedchem.6b01642
Rattus norvegicus Bile salt export pump Activity nan None 10.1053/jhep.2000.8263
Rattus norvegicus Multidrug resistance protein 1a Activity 16.0 % 10.1016/0270-9139(94)90150-3
None ADMET LD50 150.0 uM 10.1016/j.ejmech.2016.01.002
None Hepatotoxicity DILI positive/negative 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity Hepatotoxicity nan None 10.1124/dmd.110.035113

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013267 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_50042
AKRT013268 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C MNXR162470
AKRT013269 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C>>NCCS(=O)(=O)O MNXR162470
AKRT013270 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C BILE-SALT-SULFOTRANSFERASE-RXN
AKRT013275 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@@]21C>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_50130
AKRT013338 C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C.NCCS(=O)(=O)O>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_31614