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

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

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
Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia.	2004-08	15178557
The effect of LXR activators on AP-1 proteins in keratinocytes.	2004-07	15191540
Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS.	2004-06-01	15136164
Analysis of cholesterol oxidation products in biological samples.	2004-05-29	15164842
Rat cytochrome P450C24 (CYP24A1) and the role of F249 in substrate binding and catalytic activity.	2004-05-15	15111121
Sterol regulation of scavenger receptor class B type I in macrophages.	2004-05	14967816
Signaling pathway of magnolol-stimulated lipolysis in sterol ester-loaded 3T3-L1 preadipocyes.	2004-04-01	15034936
Oxysterols regulate expression of the steroidogenic acute regulatory protein.	2004-04	15072555
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.	2004-03-26	15046640
Effect of LPS on basal and induced apo E secretion by 25-OH chol and 9cRA in differentiated CaCo-2.	2004-03-01	14991770
Apomine, a novel hypocholesterolemic agent, accelerates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and stimulates low density lipoprotein receptor activity.	2004-02-20	14627708
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.	2004-02	15084352
AKT/protein kinase B regulation of BCL family members during oxysterol-induced apoptosis.	2004-01-09	14559920
CYP3A induction by liver x receptor ligands in primary cultured rat and mouse hepatocytes is mediated by the pregnane X receptor.	2004-01	14709622
Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.	2003-12-15	14635199
Cholesterol oxides mediated changes in cytoskeletal organisation involves Rho GTPases.	2003-12-10	14644170
Steroid structural requirements for stabilizing or disrupting lipid domains.	2003-12-09	14640695
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.	2003-12-01	14622968
Clofibrate, a peroxisome-proliferator, enhances reverse cholesterol transport through cytochrome P450 activation and oxysterol generation.	2003-12	14690017
In vivo implants of beta-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus).	2003-12	14636632
Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.	2003-12	14615881
Cholesterol transport and steroidogenesis by the corpus luteum.	2003-11-10	14613534
Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man.	2003-10-15	14556856
7-ketocholesterol stimulates differentiation of lens epithelial cells.	2003-10-06	14551533
Origin of oxysterols in hepatic bile of patients with biliary infection.	2003-10	14572579
Involvement of the SREBP pathway in the mode of action of androgens in sebaceous glands in vivo.	2003-08	12930306
Direct effect of propylthiouracil on progesterone release in rat granulosa cells.	2003-08	12922945
On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation.	2003-08	12777473
NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols.	2003-07-11	12719428
Sterol-mediated regulation of hormone-sensitive lipase in 3T3-L1 adipocytes.	2003-07	14506837
Oxysterols suppress constitutive fibrinogen expression.	2003-07	12876624
Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol.	2003-06-10	12794941
Oxysterol-induced toxicity in R28 and ARPE-19 cells.	2003-06	12718442
Effects of dioxin (2,3,7,8-TCDD) and PCDDs/PCDFs congeners mixture on steroidogenesis in human placenta tissue culture.	2003-03	12916318
PPAR agonists protect mesangial cells from interleukin 1beta-induced intracellular lipid accumulation by activating the ABCA1 cholesterol efflux pathway.	2003-03	12595494
Regulation of isoprenoid/cholesterol biosynthesis in cells from mevalonate kinase-deficient patients.	2003-02-21	12477733
Oxysterols induce apoptosis and accumulation of cell cycle at G(2)/M phase in the human monocytic THP-1 cell line.	2003-02-07	12527036
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.	2003-02	12542530
Cholesterol cell content modulates GTPase activity of G proteins in GH4C1 cell membranes.	2003-01	12401528
The effect of Puerariae radix on lipoprotein metabolism in liver and intestinal cells.	2002-12-16	12485466
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.	2002-12	12454275
Testosterone regulates 25-hydroxycholesterol production in testicular macrophages.	2002-11	12390873
Bile acids enhance low density lipoprotein receptor gene expression via a MAPK cascade-mediated stabilization of mRNA.	2002-10-04	12149270
Dietary cholesterol-oxidation products accumulate in serum and liver in apolipoprotein E-deficient mice, but do not accelerate atherosclerosis.	2002-10	12323083
Cholesterol addition to ER membranes alters conformation of SCAP, the SREBP escort protein that regulates cholesterol metabolism.	2002-08	12191470
Inhibition of testosterone production by propylthiouracil in rat Leydig cells.	2002-08	12135875
Effect of oxysterols on hematopoietic progenitor cells.	2002-07	12135663
Characterization of the estrogenic response to genistein in Japanese medaka (Oryzias latipes).	2002-06	12106897
Induction of hepatic inducible nitric oxide synthase by cholesterol in vivo and in vitro.	2002-05-31	12085989
The cDNA cloning and tissue expression of the cytochrome P450scc from Syrian hamster (Mesocricetus auratus).	2002-05	12093115

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:25:10 GMT 2025` Edited by `admin` on `Mon Mar 31 19:25:10 GMT 2025`
Record UNII	767JTD2N31
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

25-HYDROXYCHOLESTEROL

Systematic Name

English

25-HYDROXYCHOLESTEROL [MI]

Preferred Name

English

5-CHOLESTENE-3.BETA.,25-DIOL

Systematic Name

English

CHOLEST-5-ENE-3.BETA.,25-DIOL

Systematic Name

English

Code System Code Type Description

FDA UNII

767JTD2N31