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name Structure Reference Source Properties Activities Metabolism

Glycochenodeoxycholate

AlkaPlorer ID: AK033350

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]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-GYPHWSFCSA-N

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Reference

PubChem CID: 12544

CAS: 640-79-9

SuperNatural Ⅲ: SN0105607-04

NPASS: NPC323562

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 EC50 3000.0 nM 10.1016/s0960-894x(03)00281-6
Homo sapiens Bile acid transporter Activity 14.0 % 10.1172/jci117091
Homo sapiens Bile salt export pump Ki 7000.0 nM 10.1053/gast.2002.36591
Homo sapiens G-protein coupled bile acid receptor 1 EC50 3880.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 105.0 % 10.1021/jm7015864
Homo sapiens Ileal bile acid transporter Km 5700.0 nM 10.1152/ajpgi.1998.274.1.g157
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 80.2 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 72.0 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 65.3 % 10.1021/jm300212s
Rattus norvegicus Bile salt export pump Activity nan None 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 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 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 5600.0 nM 10.1152/ajpgi.2000.279.6.g1188
None ADMET Activity 1.053 % 10.1016/j.bmc.2010.07.030
None ADMET Activity 1.3 % 10.1016/j.bmc.2010.07.030
None ADMET Activity nan None 10.1016/j.bmc.2010.07.030
None ADMET CC50 729000.0 nM 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
AKRT013243 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]3[C@H](OS(=O)(=O)O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C 2.8.2.34-RXN
AKRT013244 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>>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.NCC(=O)O None
AKRT013246 C[C@H](CCC(=O)NCC(=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)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 53844
AKRT013247 C[C@H](CCC(=O)NCC(=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)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_1476
AKRT013248 C[C@H](CCC(=O)NCC(=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)NCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O enzymemap_852
AKRT013249 C[C@H](CCC(=O)NCC(=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)NCC(=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_50066
AKRT013250 C[C@H](CCC(=O)NCC(=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 RXN-17388
AKRT013251 C[C@H](CCC(=O)NCC(=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>>NCC(=O)O RXN-17388
AKRT013326 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.NCC(=O)O>>C[C@H](CCC(=O)NCC(=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 47112
AKRT013345 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.NCC(=O)O>>C[C@H](CCC(=O)NCC(=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-9851