5β-cholestane-3α,7α,12α-triol   Click here for help

GtoPdb Ligand ID: 2803

Compound class: Metabolite
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 60.69
Molecular weight 420.36
XLogP 7.61
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(CCCC(C1CCC2C1(C)C(O)CC1C2C(O)CC2C1(C)CCC(C2)O)C)C
Isomeric SMILES CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C)C
InChI InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key RIVQQZVHIVNQFH-XJZYBRFWSA-N
References
1. Dussault I, Yoo HD, Lin M, Wang E, Fan M, Batta AK, Salen G, Erickson SK, Forman BM. (2003)
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.
Proc Natl Acad Sci USA, 100 (3): 833-8. [PMID:12569201]
2. Goodwin B, Gauthier KC, Umetani M, Watson MA, Lochansky MI, Collins JL, Leitersdorf E, Mangelsdorf DJ, Kliewer SA, Repa JJ. (2003)
Identification of bile acid precursors as endogenous ligands for the nuclear xenobiotic pregnane X receptor.
Proc Natl Acad Sci USA, 100 (1): 223-8. [PMID:12509506]