Structure Database (LMSD)
Common Name
cholestan-6-oxo-3,5-diol
Systematic Name
cholestan-6-oxo-3β,5α-diol
Synonyms
LM ID
LMST01010126
Formula
Exact Mass
Calculate m/z
418.344696
Sum Composition
Status
Curated
3D model of cholestan-6-oxo-3,5-diol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
5α-hydroxy-6-keto Cholesterol (OCDO) is an oxysterol and active metabolite of cholesterol-5,6-epoxides.1 Cholesterol-5,6-epoxides are hydrolyzed by cholesterol epoxide hydrolase (ChEH) into cholestane-3β,5α,6β-triol, which is then dehydrogenated by 11β-hydroxysteroid dehydrogenase 2 (11β-HSD2) into OCDO. OCDO inhibits cholesterol synthesis in 16HBE cells (IC50 = 350 nM).2 It increases the proliferation of MDA-MB-231 and MDA-MB-468 cells when used at concentrations of 2 and 5 µM.3 In vivo, OCDO (50 µg/kg) increases tumor volume in MCF-7, MDA-MB-231, EO771, and MDA-MB-468 breast cancer mouse xenograft models.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
SJZZRXMQSAXCFD-ZCBMJONGSA-N
InChi (Click to copy)
InChI=1S/C27H46O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-23,28,30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,25-,26-,27+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC(=O)[C@@]3(O)C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
449.95
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
6.34
Molar Refractivity
121.95
Admin
Created at
-
Updated at
22nd Feb 2021