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
Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol.	2000 Jun 2	10748047
Direct inhibitory effect of digitalis on progesterone release from rat granulosa cells.	2001 Apr	11309248
Coronary atherosclerosis and oxidative stress as reflected by autoantibodies against oxidized low-density lipoprotein and oxysterols.	2001 Apr	11254916
Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol delta8-isomerase, a cholesterogenic enzyme with multiple functions.	2001 Feb 1	11171067
Fatty acid modifications and cholesterol oxidation in pork loin during frying at different temperatures.	2001 Jul	11456193
Concerted transcriptional activation of the low density lipoprotein receptor gene by insulin and luteinizing hormone in cultured porcine granulosa-luteal cells: possible convergence of protein kinase a, phosphatidylinositol 3-kinase, and mitogen-activated protein kinase signaling pathways.	2001 Jul	11416012
Woc (without children) gene control of ecdysone biosynthesis in Drosophila melanogaster.	2001 Jul 5	11476936
Plant sterols regulate rat vascular smooth muscle cell growth and prostacyclin release in culture.	2001 Jun	11427042
Growth modulation of low density lipoprotein receptor sterol sensitivity in cultured human fibroblasts.	2001 Nov	11795856
Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells.	2001 Oct	11590226
Cholesterol, hydroxycholesterols, and bile acids.	2002 Apr 19	11969205
Oxysterol-binding-protein (OSBP)-related protein 4 binds 25-hydroxycholesterol and interacts with vimentin intermediate filaments.	2002 Feb 1	11802775
Dissociation of apoptosis induction and CD36 upregulation by enzymatically modified low-density lipoprotein in monocytic cells.	2002 Jan 25	11798172
Scavenger receptor class B type I is expressed in cultured keratinocytes and epidermis. Regulation in response to changes in cholesterol homeostasis and barrier requirements.	2002 Jan 25	11707442
Testosterone regulates 25-hydroxycholesterol production in testicular macrophages.	2002 Nov	12390873
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
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
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
Oxysterol-induced toxicity in R28 and ARPE-19 cells.	2003 Jun	12718442
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
Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia.	2004 Aug	15178557
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
Effect of LPS on basal and induced apo E secretion by 25-OH chol and 9cRA in differentiated CaCo-2.	2004 Mar 1	14991770
Analysis of cholesterol oxidation products in biological samples.	2004 Mar-Apr	15164842

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