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
Click here for structure editor
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
References
1. Fu X, Menke JG, Chen Y, Zhou G, MacNaul KL, Wright SD, Sparrow CP, Lund EG. (2001)
27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells.
J. Biol. Chem., 276 (42): 38378-87. [PMID:11504730]
2. Lehmann JM, Kliewer SA, Moore LB, Smith-Oliver TA, Oliver BB, Su JL, Sundseth SS, Winegar DA, Blanchard DE, Spencer TA, Willson TM. (1997)
Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway.
J. Biol. Chem., 272 (6): 3137-40. [PMID:9013544]
3. Liu C, Yang XV, Wu J, Kuei C, Mani NS, Zhang L, Yu J, Sutton SW, Qin N, Banie H et al.. (2011)
Oxysterols direct B-cell migration through EBI2.
Nature, 475 (7357): 519-23. [PMID:21796211]