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
418.344695
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
1. Pulfer, M.K., and Murphy, R.C. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. The Journal of Biological Chemisty 279(25), 26331-26338 (2004).
3. Voisin, M., de Medina, P., Mallinger, A., et al. Identification of a tumor-promoter cholesterol metabolite in human breast cancers acting through the glucocorticoid receptor. Proc. Natl. Acad. Sci. USA 114(44), E9346-E9355 (2017).
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