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Tauroursodeoxycholate

AlkaPlorer ID: AK002013

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]ethanesulfonic acid

Structure

SMILES: 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

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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-LBSADWJPSA-N

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Reference

PubChem CID: 9848818

CAS: 14605-22-2

SuperNatural Ⅲ: SN0025869-10

NPASS: NPC247891

Source

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

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
Hepatitis B virus Hepatitis B virus Activity nan None 10.1021/acs.jmedchem.1c00078
Hepatitis B virus Hepatitis B virus IC50 3000.0 nM 10.1021/acs.jmedchem.1c00078
Hepatitis delta virus Hepatitis delta virus Activity 7.1 % 10.1021/acs.jmedchem.1c00078
Homo sapiens Autotaxin IC50 10300.0 nM 10.1021/acs.jmedchem.6b01743
Homo sapiens Autotaxin Inhibition nan % 10.1021/acs.jmedchem.6b01743
Homo sapiens Bile acid receptor FXR Activity 1.53 % 10.1021/np8004453
Homo sapiens Bile acid receptor FXR Activity 87.2 % 10.1021/np8004453
Homo sapiens Bile acid transporter Activity 8.0 % 10.1172/jci117091
Homo sapiens Bile acid transporter Activity nan None 10.1002/hep.510260641
Homo sapiens Bile acid transporter Inhibition nan % 10.1021/acs.jmedchem.1c00078
Homo sapiens Bile salt export pump Km 11900.0 nM 10.1053/gast.2002.36587
Homo sapiens G-protein coupled bile acid receptor 1 Activity 39.0 % 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 EC50 30000.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 EC50 50500.0 nM 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 EC50 105150.0 nM 10.1016/j.ejmech.2015.09.024
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 97.0 % 10.1021/jm7015864
Homo sapiens Histone deacetylase 6 Inhibition -24.01 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 2.03 % 10.6019/CHEMBL4808148
Homo sapiens Huh-7 Activity nan None 10.1016/j.bmcl.2016.06.059
Homo sapiens Huh-7 Inhibition nan % 10.1016/j.bmcl.2016.06.059
Homo sapiens Ileal bile acid transporter Ki 28000.0 nM 10.1152/ajpgi.1998.274.1.g157
Homo sapiens Multidrug resistance-associated protein 4 Activity 26.0 % 10.1053/jhep.2003.50331
Homo sapiens Phospholipase A2 group 1B Activity 5.0 % 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Activity 15.0 % 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Activity nan None 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B FC 1.4 None 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B FC 8.0 None 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Kd 10000.0 nM 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Ki(app) 0.000306 mole fraction 10.1021/np8004453
Homo sapiens Phospholipase A2 group 1B Ki(app) 0.005 mole fraction 10.1021/np8004453
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity 9.0 % 10.1016/0016-5085(95)90588-x
Homo sapiens Solute carrier organic anion transporter family member 1A2 Inhibition 85.7 % 10.1016/s0014-5793(98)00168-9
Homo sapiens Solute carrier organic anion transporter family member 1A2 Km 19000.0 nM 10.1016/0016-5085(95)90588-x
Rattus norvegicus Bile acid transporter Activity nan None 10.1152/ajpgi.1994.266.3.g382
Rattus norvegicus Bile acid transporter Km 14000.0 nM 10.1152/ajpgi.1998.274.2.g370
Rattus norvegicus Bile salt export pump Km 4100.0 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 nan None 10.1016/0270-9139(94)90150-3
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 13000.0 nM 10.1152/ajpgi.1999.276.4.g1037
Rattus norvegicus Solute carrier organic anion transporter family member 1A4 Km 17000.0 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 6600.0 nM 10.1152/ajpgi.2000.279.6.g1188
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 15.88 % 10.6019/CHEMBL4495564
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
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -21.08 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.14 % 10.6019/CHEMBL4495565
None ADMET Activity 1.049 % 10.1016/j.bmc.2010.07.030
None ADMET Activity 1.073 % 10.1016/j.bmc.2010.07.030
None ADMET Activity nan None 10.1016/j.bmc.2010.07.030
None ADMET CC50 1002000.0 nM 10.1016/j.bmc.2010.07.030
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx1000865
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmcl.2016.06.059
None Unchecked Activity nan None 10.1152/ajpgi.00360.2003

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013278 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@@]21C>>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_2602
AKRT013279 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@@]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 RXN-21345
AKRT013280 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@@]21C>>NCCS(=O)(=O)O RXN-21345
AKRT013343 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.NCCS(=O)(=O)O>>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@@]21C enzymemap_31611
AKRT013348 C[C@H](CCC(=O)[CoA])[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[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@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@@H]3O RXN-21376