27-hydroxycholesterol   

GtoPdb Ligand ID: 2752

Synonyms: 26-hydroxycholesterol | 27-OHC
Comment: CID 99470 shows another representation of the stereochemistry of 27-hydroxycholesterol which is commonly reported in the literature.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 40.46
Molecular weight 402.35
XLogP 8.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OCC(CCCC(C1CCC2C1(C)CCC1C2CC=C2C1(C)CCC(C2)O)C)C
Isomeric SMILES OC[C@@H](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)O)C)C
InChI InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key FYHRJWMENCALJY-YSQMORBQSA-N
Natural/Endogenous Targets
Target
GPR183
Liver X receptor-α
Liver X receptor-β
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GPR183 Hs Agonist Agonist 5.5 pEC50 - 3
pEC50 5.5 (EC50 3.029x10-6 M) [3]
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Liver X receptor-β Hs Agonist Agonist 7.2 pEC50 - 1
pEC50 7.2 [1]
Liver X receptor-α Hs Agonist Agonist 7.1 pEC50 - 1
pEC50 7.1 [1]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Targets where the ligand is described in the comment field
Target Comment