| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H46O2 |
| Molecular Weight | 402.6529 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO
InChI
InChIKey=FYHRJWMENCALJY-YSQMORBQSA-N
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
27-Hydroxycholesterol (27-HC) is an endogenous oxysterol produced by the enzyme CYP27A1, with multiple biological functions, including acting as a selective estrogen receptor modulator (SERM) and as an agonist of the liver X receptor (LXR). Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
10 mg 27-hydroxy-cholesterol dissolved in 1.0 ml of 45% aqueous solution of 2-hydroxypropyl-β-cyclodextrin (HPBCD) was administered intravenously to one group of five test rabbits.
Route of Administration:
Intravenous
COS-7 cells transfected with expression plasmids for eNOS and either ER-a or ER-b were used for activity evaluation. COS-7 cells expressing ER-a or ER-b and eNOS were incubated for 15-min with 10 nM E2 or 10 nM E2+ 20mkM 27-Hydroxycholesterol (27-HC). eNOS enzymatic activity was assessed by measuring the conversion of [3H]L-arginine (Amersham) to [3H]L-citrulline.
PARENT (METABOLITE)
SUBSTANCE RECORD
