cholesterol sulphate   

GtoPdb Ligand ID: 2738

Synonyms: cholesteryl sulfate
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 71.98
Molecular weight 466.31
XLogP 9.22
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(CCCC(C1CCC2C1(C)CCC1C2CC=C2C1(C)CCC(C2)OS(=O)(=O)O)C)C
Isomeric SMILES CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OS(=O)(=O)O)C)C
InChI InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key BHYOQNUELFTYRT-DPAQBDIFSA-N
References
1. Bitsch F, Aichholz R, Kallen J, Geisse S, Fournier B, Schlaeppi JM. (2003)
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.
Anal. Biochem., 323 (1): 139-49. [PMID:14622968]
2. Kallen JA, Schlaeppi JM, Bitsch F, Geisse S, Geiser M, Delhon I, Fournier B. (2002)
X-ray structure of the hRORalpha LBD at 1.63 A: structural and functional data that cholesterol or a cholesterol derivative is the natural ligand of RORalpha.
Structure, 10 (12): 1697-707. [PMID:12467577]