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Details

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
Structure of CHOLEST-5-ENE-3.BETA.,26-DIOL, (25R)-

SMILES

C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

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

HIDE SMILES / InChI
Molecular Formula C27H46O2
Molecular Weight 402.6529
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02314208 | https://www.ncbi.nlm.nih.gov/pubmed/28739487 | https://clinicaltrials.gov/ct2/show/NCT01180361 | https://www.ncbi.nlm.nih.gov/pubmed/17873880 | https://www.ncbi.nlm.nih.gov/pubmed/15741649

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 250.0 nM [EC50]
Antagonist
2849
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Primary
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes.
2014-02-01
Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein.
2013-03-22
Liver x receptor modulation of gene expression leading to proluteolytic effects in primate luteal cells.
2012-03
Oxysterols direct B-cell migration through EBI2.
2011-07-27
Overexpression of steroidogenic acute regulatory protein increases macrophage cholesterol efflux to apolipoprotein AI.
2010-06-01
Marked accumulation of 27-hydroxycholesterol in SPG5 patients with hereditary spastic paresis.
2010-04
FTY720 stimulates 27-hydroxycholesterol production and confers atheroprotective effects in human primary macrophages.
2010-03-05
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
2010-01
Leptin reduces the accumulation of Abeta and phosphorylated tau induced by 27-hydroxycholesterol in rabbit organotypic slices.
2010
LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms.
2009-11
Role of CYP27A1 in progesterone metabolism in vitro and in vivo.
2009-10
Oxidative damage in dengue fever.
2009-08-15
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells.
2009-01-06
Activity-regulated cytoskeleton-associated protein in rodent brain is down-regulated by high fat diet in vivo and by 27-hydroxycholesterol in vitro.
2009-01
Impact of 27-hydroxycholesterol on amyloid-beta peptide production and ATP-binding cassette transporter expression in primary human neurons.
2009
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells.
2008-12
Hypercholesterolemia-induced Abeta accumulation in rabbit brain is associated with alteration in IGF-1 signaling.
2008-12
Regulation of alpha-synuclein expression by liver X receptor ligands in vitro.
2008-11-19
Niemann-Pick C1 protects against atherosclerosis in mice via regulation of macrophage intracellular cholesterol trafficking.
2008-06
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008-05
Glucocorticoid receptor-mediated upregulation of human CYP27A1, a potential anti-atherogenic enzyme.
2008-03-31
Effectors of rapid homeostatic responses of endoplasmic reticulum cholesterol and 3-hydroxy-3-methylglutaryl-CoA reductase.
2008-01-18
27-hydroxycholesterol is an endogenous selective estrogen receptor modulator.
2008-01
27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen.
2007-10
24S-hydroxycholesterol in relation to disease manifestations of acute experimental autoimmune encephalomyelitis.
2007-05-15
PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine.
2007-02
Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization.
2006-05-25
Detection of the steroidogenic acute regulatory protein, StAR, in human liver cells.
2005-04-15
Regulation of sterol 27-hydroxylase in human monocyte-derived macrophages: up-regulation by transforming growth factor beta1.
2005-02-21
Serum cholestenoic acid as a potential marker of pulmonary cholesterol homeostasis: increased levels in patients with pulmonary alveolar proteinosis.
2004-12
27-Hydroxycholesterol inhibits neutral sphingomyelinase in cultured human endothelial cells.
2004-08-13
Oxysterol regulation of steroidogenic acute regulatory protein gene expression. Structural specificity and transcriptional and posttranscriptional actions.
1998-11-13
Activities of recombinant human cytochrome P450c27 (CYP27) which produce intermediates of alternative bile acid biosynthetic pathways.
1998-07-17
Sterol 27-hydroxylase: expression in human arterial endothelium.
1997-06
Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols.
1997-05-13
Localization of sterol 27-hydroxylase immuno-reactivity in human atherosclerotic plaques.
1997-02-18
Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase.
1997-02-18
Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway.
1997-02-07
Effects of cyclosporin on cholesterol 27-hydroxylation and LDL receptor activity in HepG2 cells.
1996-01
Esterification of oxysterols by human plasma lecithin-cholesterol acyltransferase.
1995-05-19
7 Alpha-hydroxylation of 27-hydroxycholesterol in rat brain microsomes.
1995-03
Effects of 26-aminocholesterol, 27-hydroxycholesterol, and 25-hydroxycholesterol on proliferation and cholesterol homeostasis in arterial myocytes.
1995-03
Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis.
1995-02
27-Hydroxycholesterol modulation of low density lipoprotein metabolism in cultured human hepatic and extrahepatic cells.
1993-10-11
Synthesis of 27-hydroxycholesterol in rat liver mitochondria: HPLC assay and marked activation by exogenous cholesterol.
1993-04
Formation of 7 alpha- and 7 beta-hydroxylated bile acid precursors from 27-hydroxycholesterol in human liver microsomes and mitochondria.
1993-03
24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver.
1993-02-24
26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate.
1986-12
Bile acid metabolism in cirrhosis. VIII. Quantitative evaluation of bile acid synthesis from [7 beta-3H]7 alpha-hydroxycholesterol and [G-3H]26-hydroxycholesterol.
1982-01-01
Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man.
1976-02-15
Patents

Patents

06645953
1
20040266663
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:12:22 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:22 GMT 2025
Record UNII
6T2NA6P5SQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-226105
Preferred Name English
CHOLEST-5-ENE-3.BETA.,26-DIOL, (25R)-
Systematic Name English
(3.BETA.,25R)-CHOLEST-5-ENE-3,26-DIOL
Systematic Name English
(-)-(25R)-26-HYDROXYCHOLESTEROL
Systematic Name English
(25R)-26-HYDROXYCHOLESTEROL
Systematic Name English
26-HYDROXYCHOLESTEROL, (25R)-
Systematic Name English
CHOLEST-5-ENE-3,26-DIOL, (3.BETA.,25R)-
Systematic Name English
(25R)-CHOLEST-5-ENE-3.BETA.,26-DIOL
Systematic Name English
27-HYDROXYCHOLESTEROL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C843
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
Code System Code Type Description
FDA UNII
6T2NA6P5SQ
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID40864941
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
WIKIPEDIA
27-HYDROXYCHOLESTEROL
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
CAS
13095-61-9
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
NSC
226105
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
CHEBI
17703
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
CAS
20380-11-4
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
NCI_THESAURUS
C123794
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY NCIT
PUBCHEM
123976
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
CHEBI
76591
Created by admin on Mon Mar 31 18:12:22 GMT 2025 , Edited by admin on Mon Mar 31 18:12:22 GMT 2025
PRIMARY
Related Record Type Details
Structure of CHOLESTEROL
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