U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
250.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate.
1986 Dec
Sterol 27-hydroxylase: expression in human arterial endothelium.
1997 Jun
Activities of recombinant human cytochrome P450c27 (CYP27) which produce intermediates of alternative bile acid biosynthetic pathways.
1998 Jul 17
Oxysterol regulation of steroidogenic acute regulatory protein gene expression. Structural specificity and transcriptional and posttranscriptional actions.
1998 Nov 13
Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol.
2000 Jun 2
Immune complexes and IFN-gamma decrease cholesterol 27-hydroxylase in human arterial endothelium and macrophages.
2001 Nov
Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4.
2001 Oct 19
NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols.
2003 Jul 11
27-Hydroxycholesterol inhibits neutral sphingomyelinase in cultured human endothelial cells.
2004 Aug 13
Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease.
2004 Jan
Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization.
2006 May 25
PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine.
2007 Feb
27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen.
2007 Oct
27-hydroxycholesterol is an endogenous selective estrogen receptor modulator.
2008 Jan
Glucocorticoid receptor-mediated upregulation of human CYP27A1, a potential anti-atherogenic enzyme.
2008 Nov-Dec
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
LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms.
2009 Nov
Oxysterols direct B-cell migration through EBI2.
2011 Jul 27
Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein.
2013 Mar 22
Patents

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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:53:43 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
Code System Code Type Description
FDA UNII
6T2NA6P5SQ
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID40864941
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
WIKIPEDIA
27-HYDROXYCHOLESTEROL
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
CAS
13095-61-9
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
NSC
226105
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
CHEBI
17703
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
CAS
20380-11-4
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
NCI_THESAURUS
C123794
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY NCIT
PUBCHEM
123976
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
CHEBI
76591
Created by admin on Fri Dec 15 15:53:44 UTC 2023 , Edited by admin on Fri Dec 15 15:53:44 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
PREDOMINANTLY METABOLIZED IN MACROPHAGES
MAJOR