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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H46O2
Molecular Weight 402.6529
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 25-HYDROXYCHOLESTEROL

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)CCCC(C)(C)O

InChI

InChIKey=INBGSXNNRGWLJU-ZHHJOTBYSA-N
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H46O2
Molecular Weight 402.6529
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Cholesterol addition to ER membranes alters conformation of SCAP, the SREBP escort protein that regulates cholesterol metabolism.
2002 Aug
Inhibition of testosterone production by propylthiouracil in rat Leydig cells.
2002 Aug
On the rate of translocation in vitro and kinetics in vivo of the major oxysterols in human circulation: critical importance of the position of the oxygen function.
2002 Dec
The effect of Puerariae radix on lipoprotein metabolism in liver and intestinal cells.
2002 Dec 16
Effect of oxysterols on hematopoietic progenitor cells.
2002 Jul
Characterization of the estrogenic response to genistein in Japanese medaka (Oryzias latipes).
2002 Jun
The cDNA cloning and tissue expression of the cytochrome P450scc from Syrian hamster (Mesocricetus auratus).
2002 May
Induction of hepatic inducible nitric oxide synthase by cholesterol in vivo and in vitro.
2002 May 31
Testosterone regulates 25-hydroxycholesterol production in testicular macrophages.
2002 Nov
Dietary cholesterol-oxidation products accumulate in serum and liver in apolipoprotein E-deficient mice, but do not accelerate atherosclerosis.
2002 Oct
Bile acids enhance low density lipoprotein receptor gene expression via a MAPK cascade-mediated stabilization of mRNA.
2002 Oct 4
Involvement of the SREBP pathway in the mode of action of androgens in sebaceous glands in vivo.
2003 Aug
Direct effect of propylthiouracil on progesterone release in rat granulosa cells.
2003 Aug
On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation.
2003 Aug
Clofibrate, a peroxisome-proliferator, enhances reverse cholesterol transport through cytochrome P450 activation and oxysterol generation.
2003 Dec
In vivo implants of beta-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus).
2003 Dec
Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.
2003 Dec
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.
2003 Dec 1
Cholesterol oxides mediated changes in cytoskeletal organisation involves Rho GTPases.
2003 Dec 10
Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.
2003 Dec 15
Steroid structural requirements for stabilizing or disrupting lipid domains.
2003 Dec 9
Liver X receptor activators display anti-inflammatory activity in irritant and allergic contact dermatitis models: liver-X-receptor-specific inhibition of inflammation and primary cytokine production.
2003 Feb
Regulation of isoprenoid/cholesterol biosynthesis in cells from mevalonate kinase-deficient patients.
2003 Feb 21
Oxysterols induce apoptosis and accumulation of cell cycle at G(2)/M phase in the human monocytic THP-1 cell line.
2003 Feb 7
Cholesterol cell content modulates GTPase activity of G proteins in GH4C1 cell membranes.
2003 Jan
Sterol-mediated regulation of hormone-sensitive lipase in 3T3-L1 adipocytes.
2003 Jul
Oxysterols suppress constitutive fibrinogen expression.
2003 Jul
NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols.
2003 Jul 11
Oxysterol-induced toxicity in R28 and ARPE-19 cells.
2003 Jun
Effects of dioxin (2,3,7,8-TCDD) and PCDDs/PCDFs congeners mixture on steroidogenesis in human placenta tissue culture.
2003 Mar
PPAR agonists protect mesangial cells from interleukin 1beta-induced intracellular lipid accumulation by activating the ABCA1 cholesterol efflux pathway.
2003 Mar
Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol.
2003 May-Jun
Cholesterol transport and steroidogenesis by the corpus luteum.
2003 Nov 10
Origin of oxysterols in hepatic bile of patients with biliary infection.
2003 Oct
Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man.
2003 Oct 15
7-ketocholesterol stimulates differentiation of lens epithelial cells.
2003 Oct 6
Oxysterols regulate expression of the steroidogenic acute regulatory protein.
2004 Apr
Signaling pathway of magnolol-stimulated lipolysis in sterol ester-loaded 3T3-L1 preadipocyes.
2004 Apr 1
Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia.
2004 Aug
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.
2004 Feb
Apomine, a novel hypocholesterolemic agent, accelerates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and stimulates low density lipoprotein receptor activity.
2004 Feb 20
CYP3A induction by liver x receptor ligands in primary cultured rat and mouse hepatocytes is mediated by the pregnane X receptor.
2004 Jan
AKT/protein kinase B regulation of BCL family members during oxysterol-induced apoptosis.
2004 Jan 9
The effect of LXR activators on AP-1 proteins in keratinocytes.
2004 Jul
Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS.
2004 Jun 1
Effect of LPS on basal and induced apo E secretion by 25-OH chol and 9cRA in differentiated CaCo-2.
2004 Mar 1
NFY interacts with the promoter region of two genes involved in the rat peroxisomal fatty acid beta-oxidation: the multifunctional protein type 1 and the 3-ketoacyl-CoA B thiolase.
2004 Mar 26
Analysis of cholesterol oxidation products in biological samples.
2004 Mar-Apr
Sterol regulation of scavenger receptor class B type I in macrophages.
2004 May
Rat cytochrome P450C24 (CYP24A1) and the role of F249 in substrate binding and catalytic activity.
2004 May 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 18:54:06 GMT 2023
Edited
by admin
on Fri Dec 15 18:54:06 GMT 2023
Record UNII
767JTD2N31
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
25-HYDROXYCHOLESTEROL
MI  
Systematic Name English
5-CHOLESTENE-3.BETA.,25-DIOL
Systematic Name English
CHOLEST-5-ENE-3.BETA.,25-DIOL
Systematic Name English
25-HYDROXYCHOLESTEROL [MI]
Common Name English
Code System Code Type Description
FDA UNII
767JTD2N31
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID5044023
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
CAS
2140-46-7
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
PUBCHEM
65094
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
DRUG BANK
DB04705
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
CHEBI
42977
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
MERCK INDEX
m6130
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY Merck Index
MESH
C007997
Created by admin on Fri Dec 15 18:54:07 GMT 2023 , Edited by admin on Fri Dec 15 18:54:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
25-HYDROXYCHOLESTEROL activates the ER-localized enzyme ACAT to induce internalization of accessible cholesterol on the plasma membrane and restricts SARS-CoV-2 S protein-mediated fusion which inhibits virus replication