Compound: 27-hydroxycholesterol
SMILES: O[C@@H]1CC2=CC[C@H]3[C@H]4[C@]([C@@H]([C@@H](CCC[C@H](CO)C)C)CC4)(C)CC[C@@H]3[C@@]2(C)CC1
InChIKey: FYHRJWMENCALJY-YSQMORBQSA-N
Synonyms: 27-hydroxycholesterol, 20380-11-4, (25R)-26-Hydroxycholesterol, (25R)-Cholest-5-ene-3beta,26-diol, Cholest-5-ene-3beta,27-diol, 5-cholestene-3 beta,27-diol, 6T2NA6P5SQ, 27HC, (3beta,25R)-cholest-5-ene-3,26-diol, Cholest-5-ene-3beta,26-diol, (25R)-, CHEBI:76591, DTXSID40864941, NSC-226105, (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, Cholest-5-ene-3,26,diol, (3beta,25R)-, 26-hydroxycholesterol, (25R), cholest-5-ene-3 beta,27-diol, (3S,8S,9S,10R,13R,14S,17R)-17-((2R,6R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol, (25R)-cholest-5-ene-3 beta,26-diol, (3 beta,25R)-cholest-5-ene-3,26-diol, cholest-5-ene-3 beta,26-diol, (25R)-, RefChem:905787, 27OHC, DTXCID201474789, (3S,8S,9S,10R,13R,14S,17R)-17-((2R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol, cholest-(25R)-5-en-3beta,26-diol, 27-hydroxy-cholesterol(25R), cholest-5-ene-3,26-diol, (3beta,25R)-, (25R)-26-?Hydroxycholesterol, 25(R)-27-hydroxy Cholesterol, 5,25R-Cholesten-3beta,26-diol, cholest-(25R)-5-ene-3|A,27-diol, (3S,8S,9S,10R,13R,14S,17R)-17-((2R,6R)-7-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol, (3S,8S,9S,10R,13R,14S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, UNII-6T2NA6P5SQ, 27-HC, MFCD00272990, 26-hydroxycholesterol(25R), 5-cholestene-3beta,27-diol, SCHEMBL288494, CHEMBL353882, Cholest-5-ene-3-b,27-diol, GTPL2752, orb1296084, orb3141102, (25R)-26-hydroxy cholesterol, SCHEMBL31281328, BDBM20183, Cholest-5-ene-3-beta,27-diol, FYHRJWMENCALJY-YSQMORBQSA-N, GLXC-05343, 13095-61-9, HY-N2371, 5-,25r-Cholesten-3beta,26-diol, LMST01010088, (25R)-Cholest-5-ene-3b,26-diol, (3-beta)-cholest-5-ene-3,26-diol, AKOS027381276, CS-6949, EBC-615674, (3b,25R)-Cholest-5-ene-3,26-diol, 26-HYDROXYCHOLESTEROL, (25R)-, (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol, FC146890, MS-26874, PD018880, (3beta,25R)-Cholest-5-ene-3,26,diol, (-)-(25R)-26-HYDROXYCHOLESTEROL, NS00121507, Cholest-5-ene-3,26-diol, (3|A,25R)-, (25R)-CHOLEST-5-ENE-3.BETA.,26-DIOL, (3.BETA.,25R)-CHOLEST-5-ENE-3,26-DIOL, CHOLEST-5-ENE-3.BETA.,26-DIOL, (25R)-, Q15634124, CHOLEST-5-ENE-3,26-DIOL, (3.BETA.,25R)-, (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-7-en-5-ol
Theoretical properties:
molecular_formula: C27H46O2
molecular_weight: 402.7 g/mol
exact_mass: 402.349780706 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 6
heavy_atom_count: 29
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (25R)-cholest-5-ene-3beta,26-diol is a 26-hydroxycholesterol in which the 25-position has R-configuration. It has a role as a neuroprotective agent, an apoptosis inducer, a mouse metabolite and a human metabolite. It is functionally related to a cholesterol.
chebi: A 26-hydroxycholesterol in which the 25-position has <i>R</i>-configuration.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1.
A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1. 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. As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.