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name Structure Reference Source Properties Activities Metabolism

Taurochenodeoxycholate

AlkaPlorer ID: AK002010

Synonym: None

IUPAC Name: 2-[[(4R)-4-[(3R,5S,7R,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]ethanesulfonic acid

Structure

SMILES: C[C@H](CC/C(O)=N/CCS(=O)(=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/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1

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InChIKey: BHTRKEVKTKCXOH-BJLOMENOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 499.71400000000034

TPSA？: 127.42000000000002

MolLogP？: 4.237600000000003

Number of H-Donors: 4

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Bile acid receptor FXR EC50 3000.0 nM 10.1016/s0960-894x(03)00281-6
Homo sapiens Bile acid transporter Activity 19.0 % 10.1172/jci117091
Homo sapiens Bile acid transporter Activity nan None 10.1002/hep.510260641
Homo sapiens Bile salt export pump Ki 28000.0 nM 10.1053/gast.2002.36591
Homo sapiens Bile salt export pump Km 4800.0 nM 10.1053/gast.2002.36587
Homo sapiens Cytochrome P450 3A4 Log 1/Km -1.954 None 10.1016/j.bmcl.2005.06.015
Homo sapiens G-protein coupled bile acid receptor 1 Activity 92.0 % 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 EC50 1920.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 EC50 2300.0 nM 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 EC50 29570.0 nM 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 103.0 % 10.1021/jm7015864
Homo sapiens Ileal bile acid transporter Ki 6100.0 nM 10.1152/ajpgi.1998.274.1.g157
Homo sapiens Multidrug resistance associated protein Activity 6.0 % 10.1042/bj20021081
Homo sapiens Multidrug resistance-associated protein 4 Activity 11.0 % 10.1053/jhep.2003.50331
Homo sapiens Multidrug resistance-associated protein 4 IC50 55000.0 nM 10.1042/bj20021886
Homo sapiens P-glycoprotein 1 Activity 66.0 % 10.1016/0270-9139(94)90150-3
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity 17.0 % 10.1016/0016-5085(95)90588-x
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity 28.0 % 10.1016/0016-5085(95)90588-x
Homo sapiens Solute carrier organic anion transporter family member 1A2 Inhibition 75.2 % 10.1016/s0014-5793(98)00168-9
Homo sapiens Solute carrier organic anion transporter family member 1A2 Inhibition 91.0 % 10.1016/s0168-8278(96)80246-7
Homo sapiens Solute carrier organic anion transporter family member 1A2 Inhibition 100.0 % 10.1016/s0168-8278(96)80246-7
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 89.5 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 82.4 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 47.2 % 10.1021/jm300212s
Mus musculus Bile salt export pump Activity 25.0 % 10.1016/s0378-1119(99)00460-6
Mus musculus Bile salt export pump Km 5700.0 nM 10.1053/jhep.2001.24171
Oryctolagus cuniculus Oryctolagus cuniculus IC25 13.0 uM 10.1021/jm00033a001
Oryctolagus cuniculus Oryctolagus cuniculus IC25 13.0 uM 10.1021/jm00046a007
Oryctolagus cuniculus Oryctolagus cuniculus IC50 28000.0 nM 10.1021/jm00033a001
Oryctolagus cuniculus Oryctolagus cuniculus IC50 28000.0 nM 10.1021/jm00046a007
Oryctolagus cuniculus Oryctolagus cuniculus IC75 61.0 uM 10.1021/jm00033a001
Oryctolagus cuniculus Oryctolagus cuniculus IC75 61.0 uM 10.1021/jm00046a007
Rattus norvegicus Bile acid transporter Activity nan None 10.1073/pnas.88.23.10629
Rattus norvegicus Bile acid transporter Km 5000.0 nM 10.1152/ajpgi.1998.274.2.g370
Rattus norvegicus Bile salt export pump Km 2200.0 nM 10.1016/s0016-5085(00)70224-1
Rattus norvegicus Ileal sodium/bile acid cotransporter Activity nan None 10.1152/ajpgi.2000.279.6.g1188
Rattus norvegicus Multidrug resistance protein 1a Activity 33.0 % 10.1016/0270-9139(94)90150-3
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 10.1152/ajpgi.00352.2002
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Km 4900.0 nM None
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Km 7000.0 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 1A4 Km 12000.0 nM 10.1016/s0016-5085(99)70463-4
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 7000.0 nM 10.1152/ajpgi.2000.279.6.g1188
None ADMET Activity 1.116 % 10.1016/j.bmc.2010.07.030
None ADMET Activity 1.146 % 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
AKRT013263 C[C@H](CCC(=O)NCCS(=O)(=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>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O enzymemap_1500
AKRT013282 C[C@H](CCC(=O)NCCS(=O)(=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>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C RXN-7976
AKRT013283 C[C@H](CCC(=O)NCCS(=O)(=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>>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@]12C.NCCS(=O)(=O)O None
AKRT013286 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[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]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O MNXR149804
AKRT013288 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCCS(=O)(=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 53824
AKRT013289 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCCS(=O)(=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_1478
AKRT013290 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCCS(=O)(=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]3CC[C@@]21C 67568
AKRT013291 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](OS(=O)(=O)O)C[C@H]1C[C@H]3O enzymemap_50058
AKRT013292 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O CHENODEOXYCHOLOYLTAURINE-HYDROLASE-RXN
AKRT013293 C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O>>NCCS(=O)(=O)O CHENODEOXYCHOLOYLTAURINE-HYDROLASE-RXN
AKRT013347 C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O.NCCS(=O)(=O)O>>C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O RXN-9852