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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H46O
Molecular Weight 386.6535
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICHOLESTEROL

SMILES

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

InChI

InChIKey=HVYWMOMLDIMFJA-VEIPTCAHSA-N
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21-,22+,23-,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula C27H46O
Molecular Weight 386.6535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Preoperative lipid control with simvastatin reduces the risk for graft failure already 1 year after myocardial revascularization.
2001-02
Glycated haemoglobin, diabetes, and mortality in men in Norfolk cohort of european prospective investigation of cancer and nutrition (EPIC-Norfolk).
2001-01-06
Cholesterol reduction and non-illness mortality: meta-analysis of randomised clinical trials.
2001-01-06
Cardiovascular effects of tamoxifen in women with and without heart disease: breast cancer prevention trial. National Surgical Adjuvant Breast and Bowel Project Breast Cancer Prevention Trial Investigators.
2001-01-03
Estrogen, selective estrogen receptor modulation, and coronary heart disease: something or nothing.
2001-01-03
Hydroxy-methylglutaryl-coenzyme A reductase inhibition promotes endothelial nitric oxide synthase activation through a decrease in caveolin abundance.
2001-01-02
Effect of type 2 diabetes mellitus on left ventricular geometry and systolic function in hypertensive subjects: Hypertension Genetic Epidemiology Network (HyperGEN) study.
2001-01-02
Women's Healthy Lifestyle Project: A randomized clinical trial: results at 54 months.
2001-01-02
Cracking down on caveolin: role of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors in modulating edothelial cell nitric oxide production.
2001-01-02
Quantification of plasma membrane ergosterol of Saccharomyces cerevisiae by direct-injection atmospheric pressure chemical ionization/tandem mass spectrometry.
2001-01-01
High-density lipoprotein cholesterol and vascular stiffness at baseline in the activity counseling trial.
2001-01-01
Acute increases in plasma oxidized low-density lipoprotein immediately after percutaneous transluminal coronary angioplasty.
2001-01-01
Effects of atorvastatin versus fenofibrate on lipoprotein profiles, low-density lipoprotein subfraction distribution, and hemorheologic parameters in type 2 diabetes mellitus with mixed hyperlipoproteinemia.
2001-01-01
Pharmacological profile of F 12511, (S)-2',3', 5'-trimethyl-4'-hydroxy-alpha-dodecylthioacetanilide a powerful and systemic acylcoenzyme A: cholesterol acyltransferase inhibitor.
2001-01-01
Amyloid-beta is an antioxidant for lipoproteins in cerebrospinal fluid and plasma.
2001-01-01
Remodeling of the vessel wall after copper-induced injury is highly attenuated in mice with a total deficiency of plasminogen activator inhibitor-1.
2001-01
Life-style factors and risk for abdominal aortic aneurysm in a cohort of Finnish male smokers.
2001-01
Identification of a gene, ABCG5, important in the regulation of dietary cholesterol absorption.
2001-01
Screening family members at high risk for coronary disease. Why isn't it done?
2001-01
Frequency of the R3500Q mutation of the apolipoprotein B-100 gene in a sample screened clinically for familial hypercholesterolemia in Hungary.
2001-01
Remnant-like particle (RLP) cholesterol is an independent cardiovascular disease risk factor in women: results from the Framingham Heart Study.
2001-01
Plasma lipids and cardiovascular risk: a POSCH report. Program on the Surgical Control of the Hyperlipidemias.
2001-01
The effect of a garlic preparation on plasma lipid levels in moderately hypercholesterolemic adults.
2001-01
Elevated plasma levels of free-form of TFPI antigen in hypercholesterolemic patients.
2001-01
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.
2001-01
Essential role for the (hepatic) LDL receptor in macrophage apolipoprotein E-induced reduction in serum cholesterol levels and atherosclerosis.
2001-01
Raloxifene and estrogen reduces progression of advanced atherosclerosis--a study in ovariectomized, cholesterol-fed rabbits.
2001-01
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.
2001-01
Gelatin intake increases the atheroma formation in apoE knock out mice.
2001-01
The LDL receptor is the major pathway for beta-VLDL uptake by mouse peritoneal macrophages.
2001-01
17beta-estradiol, gender independently, reduces atheroma development but not neointimal proliferation after balloon injury in the rabbit aorta.
2001-01
Inability of plasma high-density lipoproteins to inhibit cell adhesion molecule expression in human coronary artery endothelial cells.
2001-01
The sialylation of plasma lipoproteins.
2001-01
Alcohol intake, type of beverage, and the risk of cerebral infarction in young women.
2001-01
Ask the doctor. I've been fighting obesity all my life. I'm a 62-year-old woman and every five years or so I lose about 20 pounds, then slowly gain it back. I've heard that this "yo-yo" pattern of weight loss, weight gain, weight loss, may be more dangerous than just staying heavy. Should I give up trying to lose weight?
2001-01
Ursodeoxycholic acid alone or with chenodeoxycholic acid for dissolution of cholesterol gallstones: a randomized multicentre trial. The British-Italian Gallstone Study group.
2001-01
PPAR-alpha and PPAR-gamma activators induce cholesterol removal from human macrophage foam cells through stimulation of the ABCA1 pathway.
2001-01
The role of PPAR-gamma in macrophage differentiation and cholesterol uptake.
2001-01
Resolution of alcohols by cholesterol oxidase fromRrhodococcus erythropolis: lack of enantiospecificity for the steroids.
2001-01
Effect of lipid reduction on the progression of renal disease: a meta-analysis.
2001-01
Accumulation of cholesterol with age in human Bruch's membrane.
2001-01
Magnetic resonance imaging and spectroscopic changes in brains of patients with cerebrotendinous xanthomatosis.
2001-01
Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period.
2001-01
Dexamethasone inhibits luteinizing hormone-induced synthesis of steroidogenic acute regulatory protein in cultured rat preovulatory follicles.
2001-01
Meiosis-activating sterol and the maturation of isolated mouse oocytes.
2001-01
Body mass index and metabolic risk factors for coronary heart disease in women.
2001-01
Maternal hypercholesterolemia during pregnancy influences the later development of atherosclerosis: clinical and pathogenic implications.
2001-01
The effect of isolated soy protein on plasma biomarkers in elderly men with elevated serum prostate specific antigen.
2001-01
Oligonucleotides as inhibitors of protein synthesis.
2001
Eight novel LDL receptor gene mutations among patients under LDL apheresis in Dresden and Leipzig.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:47:41 GMT 2025
Edited
by admin
on Mon Mar 31 21:47:41 GMT 2025
Record UNII
MP3S3KD84I
Record Status Validated (UNII)
Record Version
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Name Type Language
EPICHOLESTEROL
MI  
Common Name English
.ALPHA.-CHOLESTEROL
Preferred Name English
EPICHOLESTEROL [MI]
Common Name English
EPI-CHOLESTEROL
Common Name English
3.ALPHA.-CHOLESTEROL
Systematic Name English
CHOLEST-5-EN-3-OL, (3.ALPHA.)-
Systematic Name English
3-EPICHOLESTEROL
Common Name English
Code System Code Type Description
PUBCHEM
5283629
Created by admin on Mon Mar 31 21:47:41 GMT 2025 , Edited by admin on Mon Mar 31 21:47:41 GMT 2025
PRIMARY
MERCK INDEX
m4938
Created by admin on Mon Mar 31 21:47:41 GMT 2025 , Edited by admin on Mon Mar 31 21:47:41 GMT 2025
PRIMARY Merck Index
CAS
474-77-1
Created by admin on Mon Mar 31 21:47:41 GMT 2025 , Edited by admin on Mon Mar 31 21:47:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID50415281
Created by admin on Mon Mar 31 21:47:41 GMT 2025 , Edited by admin on Mon Mar 31 21:47:41 GMT 2025
PRIMARY
FDA UNII
MP3S3KD84I
Created by admin on Mon Mar 31 21:47:41 GMT 2025 , Edited by admin on Mon Mar 31 21:47:41 GMT 2025
PRIMARY