U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H46O
Molecular Weight 386.6545
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLESTEROL

SMILES

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

InChI

InChIKey=HVYWMOMLDIMFJA-DPAQBDIFSA-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 386.6545
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/28506805 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06d72b32-f4cc-4c8f-a449-91146bbc41e1

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The high level of cholesterol in the blood is a marker of hypercholesterolemia, also called dyslipidemia. As a part of homeopathic product, it helps to support general liver and gallbladder health, and is used for temporary relief of symptoms related to adrenal glands such as fatigue and low energy. Cholesterol binds to and affects the gating of a number of ion channels such as the nicotinic acetylcholine receptor (nAChR) Inwardly-rectifying K+ channels (Kir); Transient receptor potential vanilloid 1 channels (TRPV1) and Large-conductance Ca2+-sensitive voltage-gated K+ channels (BK). It was shown the new mechanistic insights into the role of cholesterol in the regulation of nAChR, showing that cholesterol regulates the channels by two distinct mechanisms: stabilization of the channels in a resting state that depends on specific lipid-protein interactions and facilitation of the transitions between uncoupled and coupled states that depends on the hydrophobic thickness of the membrane

CNS Activity

Curator's Comment:: a low synthesis of cholesterol is present in the brain, a mechanism for compensatory elimination is required. It was discovered, that favoured mechanism for this involves conversion into 24S-hydroxycholesterol, followed by diffusion over the blood-brain barrier

Approval Year

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 10 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Preoperative lipid control with simvastatin reduces the risk for graft failure already 1 year after myocardial revascularization.
2001 Feb
Peroxisome proliferator-activated receptor alpha is not rate-limiting for the lipoprotein-lowering action of fish oil.
2001 Feb 16
Sterol-modulated glycolipid sorting occurs in niemann-pick C1 late endosomes.
2001 Feb 2
Accumulation and aggregation of amyloid beta-protein in late endosomes of Niemann-pick type C cells.
2001 Feb 9
Caveolin-1 binding to endoplasmic reticulum membranes and entry into the regulated secretory pathway are regulated by serine phosphorylation. Protein sorting at the level of the endoplasmic reticulum.
2001 Feb 9
Frequency of the R3500Q mutation of the apolipoprotein B-100 gene in a sample screened clinically for familial hypercholesterolemia in Hungary.
2001 Jan
Elevated plasma levels of free-form of TFPI antigen in hypercholesterolemic patients.
2001 Jan
Gelatin intake increases the atheroma formation in apoE knock out mice.
2001 Jan
The LDL receptor is the major pathway for beta-VLDL uptake by mouse peritoneal macrophages.
2001 Jan
The sialylation of plasma lipoproteins.
2001 Jan
Ursodeoxycholic acid alone or with chenodeoxycholic acid for dissolution of cholesterol gallstones: a randomized multicentre trial. The British-Italian Gallstone Study group.
2001 Jan
PPAR-alpha and PPAR-gamma activators induce cholesterol removal from human macrophage foam cells through stimulation of the ABCA1 pathway.
2001 Jan
Resolution of alcohols by cholesterol oxidase fromRrhodococcus erythropolis: lack of enantiospecificity for the steroids.
2001 Jan
Accumulation of cholesterol with age in human Bruch's membrane.
2001 Jan
Herbs and atherosclerosis.
2001 Jan
The benefits of niacin in atherosclerosis.
2001 Jan
Statins, hormones, and women: benefits and drawbacks for atherosclerosis and osteoporosis.
2001 Jan
Vatanidipine hydrochloride: a new long-lasting antihypertensive agent.
2001 Jan
Quantification of plasma membrane ergosterol of Saccharomyces cerevisiae by direct-injection atmospheric pressure chemical ionization/tandem mass spectrometry.
2001 Jan 1
High-density lipoprotein cholesterol and vascular stiffness at baseline in the activity counseling trial.
2001 Jan 1
Acute increases in plasma oxidized low-density lipoprotein immediately after percutaneous transluminal coronary angioplasty.
2001 Jan 1
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 Jan 1
Amyloid-beta is an antioxidant for lipoproteins in cerebrospinal fluid and plasma.
2001 Jan 1
Effect of type 2 diabetes mellitus on left ventricular geometry and systolic function in hypertensive subjects: Hypertension Genetic Epidemiology Network (HyperGEN) study.
2001 Jan 2
Reduction of isoprostanes and regression of advanced atherosclerosis by apolipoprotein E.
2001 Jan 5
Glycated haemoglobin, diabetes, and mortality in men in Norfolk cohort of european prospective investigation of cancer and nutrition (EPIC-Norfolk).
2001 Jan 6
Cellular stress induces the tyrosine phosphorylation of caveolin-1 (Tyr(14)) via activation of p38 mitogen-activated protein kinase and c-Src kinase. Evidence for caveolae, the actin cytoskeleton, and focal adhesions as mechanical sensors of osmotic stress.
2001 Mar 16
Cholesterol depletion disrupts caveolae and insulin receptor signaling for metabolic control via insulin receptor substrate-1, but not for mitogen-activated protein kinase control.
2001 Mar 30
Patents

Sample Use Guides

fatigue: 1-10 drops under the tongue, 2 times a day or as directed by a health professional.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:15:44 UTC 2021
Edited
by admin
on Fri Jun 25 21:15:44 UTC 2021
Record UNII
97C5T2UQ7J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHOLESTEROL
EP   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
CHOLESTEROL [MI]
Common Name English
CHOLESTEROL [IARC]
Common Name English
CHOLESTEROL [USP-RS]
Common Name English
NSC-8798
Code English
CHOLESTEROL [VANDF]
Common Name English
CHOLESTEROL [JAN]
Common Name English
CHOLESTEROL [MART.]
Common Name English
PROVITAMIN-D
Common Name English
LIDINITE
Common Name English
DYTHOL
Common Name English
CHOLESTEROL [II]
Common Name English
CHOLESTEROL [INCI]
Common Name English
CHOLEST-5-EN-3.BETA.-OL
Systematic Name English
CHOLESTEROL [WHO-DD]
Common Name English
CHOLESTERINUM
HPUS  
Common Name English
CHOLESTEROL [EP MONOGRAPH]
Common Name English
CHOLESTERINUM [HPUS]
Common Name English
LIDINIT
Common Name English
CHOLEST-5-EN-3-OL (3.BETA.)-
Common Name English
CHOLESTEROL [HSDB]
Common Name English
Classification Tree Code System Code
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IARC Cholesterol
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LOINC 54438-7
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
LOINC 55440-2
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
200-353-2
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
HSDB
7106
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
WIKIPEDIA
CHOLESTEROL
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY
DRUG BANK
DB04540
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
MERCK INDEX
M3478
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY Merck Index
CAS
57-88-5
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL112570
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
NCI_THESAURUS
C369
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY
PUBCHEM
5997
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY
EPA CompTox
57-88-5
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
FDA UNII
97C5T2UQ7J
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
MESH
D002784
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY
EVMPD
SUB12480MIG
Created by admin on Fri Jun 25 21:15:44 UTC 2021 , Edited by admin on Fri Jun 25 21:15:44 UTC 2021
PRIMARY
USP_CATALOG
1131960
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY USP-RS
RXCUI
2438
Created by admin on Fri Jun 25 21:15:45 UTC 2021 , Edited by admin on Fri Jun 25 21:15:45 UTC 2021
PRIMARY RxNorm
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