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

Details

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

SHOW SMILES / InChI
Structure of CHOLESTEROL

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

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

Description
Curator's Comment: description was created based on several sources, including 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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P63252
Gene ID: 3759.0
Gene Symbol: KCNJ2
Target Organism: Homo sapiens (Human)
Target ID: Q8NER1
Gene ID: 7442.0
Gene Symbol: TRPV1
Target Organism: Homo sapiens (Human)
Conditions
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
A common mutation of the insulin receptor substrate-1 gene is a risk factor for coronary artery disease.
1999 Dec
Progesterone synthesized by Schwann cells during myelin formation regulates neuronal gene expression.
2000 Jul
24-hydroxycholesterol is a substrate for hepatic cholesterol 7alpha-hydroxylase (CYP7A).
2000 Oct
Squalene synthase: structure and regulation.
2001
Preoperative lipid control with simvastatin reduces the risk for graft failure already 1 year after myocardial revascularization.
2001 Feb
The effect of a single gavage dose of fumonisin B(1) on the sphinganine and sphingosine levels in vervet monkeys.
2001 Feb-Mar
A comparison of the toxinological characteristics of two Cassiopea and Aurelia species.
2001 Feb-Mar
Life-style factors and risk for abdominal aortic aneurysm in a cohort of Finnish male smokers.
2001 Jan
Plasma lipids and cardiovascular risk: a POSCH report. Program on the Surgical Control of the Hyperlipidemias.
2001 Jan
Inability of plasma high-density lipoproteins to inhibit cell adhesion molecule expression in human coronary artery endothelial cells.
2001 Jan
The sialylation of plasma lipoproteins.
2001 Jan
Alcohol intake, type of beverage, and the risk of cerebral infarction in young women.
2001 Jan
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 Jan
Meiosis-activating sterol and the maturation of isolated mouse oocytes.
2001 Jan
The effect of isolated soy protein on plasma biomarkers in elderly men with elevated serum prostate specific antigen.
2001 Jan
Active urea transport and an unusual basolateral membrane composition in the gills of a marine elasmobranch.
2001 Jan
Herbs and atherosclerosis.
2001 Jan
The role of fibric acids in atherosclerosis.
2001 Jan
Fatty acid bile acid conjugates (FABACs)--new molecules for the prevention of cholesterol crystallisation in bile.
2001 Jan
Decline of the relative risk of death associated with low employment grade at older age: the impact of age related differences in smoking, blood pressure and plasma cholesterol.
2001 Jan
The loop region covering the iron-sulfur cluster in bovine adrenodoxin comprises a new interaction site for redox partners.
2001 Jan 12
Reduction of isoprostanes and regression of advanced atherosclerosis by apolipoprotein E.
2001 Jan 5
Isoform-specific localization of voltage-gated K+ channels to distinct lipid raft populations. Targeting of Kv1.5 to caveolae.
2001 Mar 16
Patents

Sample Use Guides

fatigue: 1-10 drops under the tongue, 2 times a day or as directed by a health professional. gallbladder health: Adults: Take five granules three times daily or as recommended by your healthcare practitioner. Children: Take three garnules and follow adult directions.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:21:21 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:21 GMT 2023
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
Cholesterol [WHO-DD]
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
ALF component cholesterol
Common Name English
Army Liposome Formulation component cholesterol
Common Name English
CHOLESTEROL [INCI]
Common Name English
Cholest-5-en-3β-ol
Systematic 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
ALFQ component cholesterol
Common Name English
Classification Tree Code System Code
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IARC Cholesterol
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Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
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Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
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Code System Code Type Description
ECHA (EC/EINECS)
200-353-2
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
HSDB
7106
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
CHEBI
16113
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
WIKIPEDIA
CHOLESTEROL
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
DAILYMED
97C5T2UQ7J
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
NSC
8798
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
DRUG BANK
DB04540
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
SMS_ID
100000078528
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
MERCK INDEX
m3478
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY Merck Index
CAS
57-88-5
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL112570
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
NCI_THESAURUS
C369
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
PUBCHEM
5997
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022401
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
FDA UNII
97C5T2UQ7J
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
MESH
D002784
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
EVMPD
SUB12480MIG
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
RS_ITEM_NUM
1131960
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY
RXCUI
2438
Created by admin on Fri Dec 15 15:21:21 GMT 2023 , Edited by admin on Fri Dec 15 15:21:21 GMT 2023
PRIMARY RxNorm
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