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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

[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

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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 250.0 nM [EC50]
Antagonist
2778
Antagonist
2778
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
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 Jan-Feb
Esterification of oxysterols by human plasma lecithin-cholesterol acyltransferase.
1995 May 19
Localization of sterol 27-hydroxylase immuno-reactivity in human atherosclerotic plaques.
1997 Feb 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 Feb 18
Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway.
1997 Feb 7
Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols.
1997 May 13
Oxysterols in the circulation of patients with the Smith-Lemli-Opitz syndrome: abnormal levels of 24S- and 27-hydroxycholesterol.
2001 Mar
Immune complexes and IFN-gamma decrease cholesterol 27-hydroxylase in human arterial endothelium and macrophages.
2001 Nov
Transport of cholesterol into mitochondria is rate-limiting for bile acid synthesis via the alternative pathway in primary rat hepatocytes.
2002 Dec 13
Human sterol 27-hydroxylase (CYP27) overexpressor transgenic mouse model. Evidence against 27-hydroxycholesterol as a critical regulator of cholesterol homeostasis.
2002 Sep 13
Expression of sterol 27-hydroxylase (CYP27A1) enhances cholesterol efflux.
2003 Mar 28
Effects of dietary 27-hydroxycholesterol on cholesterol metabolism and bile acid biosynthesis in the hamster.
2003 Sep
Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry.
2004 Apr
Differential expression of cholesterol hydroxylases in Alzheimer's disease.
2004 Aug 13
Regulation of sterol 27-hydroxylase in human monocyte-derived macrophages: up-regulation by transforming growth factor beta1.
2005 Feb 21
PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine.
2007 Feb
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on tyrosine hydroxylase and alpha-synuclein in human neuroblastoma SH-SY5Y cells.
2008 Dec
Hypercholesterolemia-induced Abeta accumulation in rabbit brain is associated with alteration in IGF-1 signaling.
2008 Dec
Niemann-Pick C1 protects against atherosclerosis in mice via regulation of macrophage intracellular cholesterol trafficking.
2008 Jun
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008 May
Regulation of alpha-synuclein expression by liver X receptor ligands in vitro.
2008 Nov 19
Glucocorticoid receptor-mediated upregulation of human CYP27A1, a potential anti-atherogenic enzyme.
2008 Nov-Dec
Impact of 27-hydroxycholesterol on amyloid-beta peptide production and ATP-binding cassette transporter expression in primary human neurons.
2009
Oxidative damage in dengue fever.
2009 Aug 15
Activity-regulated cytoskeleton-associated protein in rodent brain is down-regulated by high fat diet in vivo and by 27-hydroxycholesterol in vitro.
2009 Jan
Differential effects of 24-hydroxycholesterol and 27-hydroxycholesterol on beta-amyloid precursor protein levels and processing in human neuroblastoma SH-SY5Y cells.
2009 Jan 6
Role of CYP27A1 in progesterone metabolism in vitro and in vivo.
2009 Oct
Leptin reduces the accumulation of Abeta and phosphorylated tau induced by 27-hydroxycholesterol in rabbit organotypic slices.
2010
Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids.
2010 Jan
Overexpression of steroidogenic acute regulatory protein increases macrophage cholesterol efflux to apolipoprotein AI.
2010 Jun 1
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 Fri Dec 15 15:53:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:53:43 GMT 2023
Record UNII
6T2NA6P5SQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
NSC-226105
Code 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 Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
Code System Code Type Description
FDA UNII
6T2NA6P5SQ
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID40864941
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
WIKIPEDIA
27-HYDROXYCHOLESTEROL
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
CAS
13095-61-9
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NSC
226105
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
CHEBI
17703
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
CAS
20380-11-4
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
NCI_THESAURUS
C123794
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY NCIT
PUBCHEM
123976
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
CHEBI
76591
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
Related Record Type Details
Structure of CHOLESTEROL
PARENT -> METABOLITE
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