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Lithoglycocholate

AlkaPlorer ID: AK022619

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]acetic acid

Structure

SMILES: C[C@H](CCC(=O)NCC(=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/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

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InChIKey: XBSQTYHEGZTYJE-OETIFKLTSA-N

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Reference

PubChem CID: 156588961

CAS: 474-74-8

NPASS: NPC323180

Source

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

Properties Information

Molecule Weight: 433.63300000000027

TPSA？: 86.63000000000001

MolLogP？: 4.623300000000004

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens ATP-binding cassette sub-family C member 11 Activity 16.0 % 10.1124/mol.104.007138
Homo sapiens Beta-galactoside alpha-2,6-sialyltransferase 1 Inhibition 9.0 % 10.1021/acs.jmedchem.0c01477
Homo sapiens Bile acid transporter Activity 24.0 % 10.1172/jci117091
Homo sapiens Ephrin type-A receptor 2 IC50 48977.88 nM 10.1021/jm301890k
Homo sapiens Ephrin type-A receptor 2 IC50 138000.0 nM 10.1021/jm301890k
Homo sapiens Ephrin type-A receptor 2 Inhibition nan % 10.1021/jm301890k
Homo sapiens G-protein coupled bile acid receptor 1 EC50 540.0 nM 10.1021/jm7015864
Homo sapiens G-protein coupled bile acid receptor 1 Efficacy 92.0 % 10.1021/jm7015864
Homo sapiens Multidrug resistance-associated protein 4 Activity 9.0 % 10.1053/jhep.2003.50331
Homo sapiens Vitamin D receptor EC50 150000.0 nM 10.1016/j.ejmech.2016.01.002
Homo sapiens Vitamin D receptor IC50 40100.0 nM 10.1016/j.ejmech.2016.01.002
Homo sapiens Vitamin D receptor IC50 50000.0 nM 10.1016/j.ejmech.2016.01.002
Rattus norvegicus CMP-N-acetylneuraminate-beta-1,4-galactoside alpha-2,3-sialyltransferase IC50 nan None 10.1021/acs.jmedchem.0c01477
Rattus norvegicus Sialyltransferase ST3Gal-I Inhibition 15.0 % 10.1021/acs.jmedchem.0c01477
Rattus norvegicus Sialyltransferase ST3Gal-I Inhibition 41.0 % 10.1021/acs.jmedchem.0c01477
None ADMET LD50 150.0 uM 10.1016/j.ejmech.2016.01.002

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013225 C[C@H](CCC(=O)NCC(=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.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C[C@H](CCC(=O)NCC(=O)OC1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)[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_34860
AKRT013226 C[C@H](CCC(=O)NCC(=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)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C enzymemap_848
AKRT013227 C[C@H](CCC(=O)NCC(=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)NCC(=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 MNXR158459
AKRT013228 C[C@H](CCC(=O)NCC(=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 MNXR162471
AKRT013229 C[C@H](CCC(=O)NCC(=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)[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 MNXR130786
AKRT013230 C[C@H](CCC(=O)NCC(=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>>NCC(=O)O MNXR130786
AKRT013231 C[C@H](CCC(=O)NCC(=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)NCC(=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 RXN-8729
AKRT013337 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.NCC(=O)O>>C[C@H](CCC(=O)NCC(=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_31617