25-HYDROXYCHOLESTEROL

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 Search

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

Title	Date	PubMed
Cholesterol addition to ER membranes alters conformation of SCAP, the SREBP escort protein that regulates cholesterol metabolism.	2002 Aug	12191470
Inhibition of testosterone production by propylthiouracil in rat Leydig cells.	2002 Aug	12135875
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	12454275
The effect of Puerariae radix on lipoprotein metabolism in liver and intestinal cells.	2002 Dec 16	12485466
Effect of oxysterols on hematopoietic progenitor cells.	2002 Jul	12135663
Characterization of the estrogenic response to genistein in Japanese medaka (Oryzias latipes).	2002 Jun	12106897
The cDNA cloning and tissue expression of the cytochrome P450scc from Syrian hamster (Mesocricetus auratus).	2002 May	12093115
Induction of hepatic inducible nitric oxide synthase by cholesterol in vivo and in vitro.	2002 May 31	12085989
Testosterone regulates 25-hydroxycholesterol production in testicular macrophages.	2002 Nov	12390873
Dietary cholesterol-oxidation products accumulate in serum and liver in apolipoprotein E-deficient mice, but do not accelerate atherosclerosis.	2002 Oct	12323083
Bile acids enhance low density lipoprotein receptor gene expression via a MAPK cascade-mediated stabilization of mRNA.	2002 Oct 4	12149270
Involvement of the SREBP pathway in the mode of action of androgens in sebaceous glands in vivo.	2003 Aug	12930306
Direct effect of propylthiouracil on progesterone release in rat granulosa cells.	2003 Aug	12922945
On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation.	2003 Aug	12777473
Clofibrate, a peroxisome-proliferator, enhances reverse cholesterol transport through cytochrome P450 activation and oxysterol generation.	2003 Dec	14690017
In vivo implants of beta-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus).	2003 Dec	14636632
Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.	2003 Dec	14615881
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	14622968
Cholesterol oxides mediated changes in cytoskeletal organisation involves Rho GTPases.	2003 Dec 10	14644170
Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.	2003 Dec 15	14635199
Steroid structural requirements for stabilizing or disrupting lipid domains.	2003 Dec 9	14640695
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	12542530
Regulation of isoprenoid/cholesterol biosynthesis in cells from mevalonate kinase-deficient patients.	2003 Feb 21	12477733
Oxysterols induce apoptosis and accumulation of cell cycle at G(2)/M phase in the human monocytic THP-1 cell line.	2003 Feb 7	12527036
Cholesterol cell content modulates GTPase activity of G proteins in GH4C1 cell membranes.	2003 Jan	12401528
Sterol-mediated regulation of hormone-sensitive lipase in 3T3-L1 adipocytes.	2003 Jul	14506837
Oxysterols suppress constitutive fibrinogen expression.	2003 Jul	12876624
NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols.	2003 Jul 11	12719428
Oxysterol-induced toxicity in R28 and ARPE-19 cells.	2003 Jun	12718442
Effects of dioxin (2,3,7,8-TCDD) and PCDDs/PCDFs congeners mixture on steroidogenesis in human placenta tissue culture.	2003 Mar	12916318
PPAR agonists protect mesangial cells from interleukin 1beta-induced intracellular lipid accumulation by activating the ABCA1 cholesterol efflux pathway.	2003 Mar	12595494
Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol.	2003 May-Jun	12794941
Cholesterol transport and steroidogenesis by the corpus luteum.	2003 Nov 10	14613534
Origin of oxysterols in hepatic bile of patients with biliary infection.	2003 Oct	14572579
Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man.	2003 Oct 15	14556856
7-ketocholesterol stimulates differentiation of lens epithelial cells.	2003 Oct 6	14551533
Oxysterols regulate expression of the steroidogenic acute regulatory protein.	2004 Apr	15072555
Signaling pathway of magnolol-stimulated lipolysis in sterol ester-loaded 3T3-L1 preadipocyes.	2004 Apr 1	15034936
Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia.	2004 Aug	15178557
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.	2004 Feb	15084352
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	14627708
CYP3A induction by liver x receptor ligands in primary cultured rat and mouse hepatocytes is mediated by the pregnane X receptor.	2004 Jan	14709622
AKT/protein kinase B regulation of BCL family members during oxysterol-induced apoptosis.	2004 Jan 9	14559920
The effect of LXR activators on AP-1 proteins in keratinocytes.	2004 Jul	15191540
Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS.	2004 Jun 1	15136164
Effect of LPS on basal and induced apo E secretion by 25-OH chol and 9cRA in differentiated CaCo-2.	2004 Mar 1	14991770
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	15046640
Analysis of cholesterol oxidation products in biological samples.	2004 Mar-Apr	15164842
Sterol regulation of scavenger receptor class B type I in macrophages.	2004 May	14967816
Rat cytochrome P450C24 (CYP24A1) and the role of F249 in substrate binding and catalytic activity.	2004 May 15	15111121

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

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Name

Type

Language

25-HYDROXYCHOLESTEROL

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