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
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
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 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:54:06 GMT 2023
by
admin
on
Fri Dec 15 18:54:06 GMT 2023
|
Record UNII |
767JTD2N31
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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
|