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

CNS Non-penetrant
1050
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

Originator

Approval Year

1992
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inward rectifier potassium channel 2
5
Target ID: P63252
Gene ID: 3759.0
Gene Symbol: KCNJ2
Target Organism: Homo sapiens (Human)
Inhibitor
8228
Transient receptor potential cation channel subfamily V member 1
6
Target ID: Q8NER1
Gene ID: 7442.0
Gene Symbol: TRPV1
Target Organism: Homo sapiens (Human)
Inhibitor
8228
Activator
1410
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Not Provided
503
Unknown

Approved Use

Unknown
Preventing
Not Provided
503
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1709

inhibitor
1579
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP7A1
1

CYP27A1
3

CYP11A1
1

CYP46A1
1

ABCG1 
1

ABCA1
1

ABCG5/8
1
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1909
 yes [Ki 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP7A1
1
 yes [Km 13.3 uM]
CYP11A1
1
 yes [Km 3.4 uM]
CYP46A1
1
 yes [Km 5.3 uM]
CYP27A1
3
 yes [Km 7 uM]
ABCA1
1
 yes
ABCG1 
1
 yes
ABCG5/8
1
 yes
CYP3A4
1709
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1632
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:16113
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16113
ChemicalBook
CB7383339
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7383339
MolPort
MolPort-002-506-911
https://www.molport.com/shop/molecule-link/MolPort-002-506-911
Selleck Chemicals
cholesterol
http://www.selleckchem.com/products/cholesterol.html
ZINC
ZINC000003875383
http://zinc15.docking.org/substances/ZINC000003875383
eMolecules
29535203
https://www.emolecules.com/cgi-bin/more?vid=29535203
eMolecules
29536225
https://www.emolecules.com/cgi-bin/more?vid=29536225
eMolecules
482145
https://www.emolecules.com/cgi-bin/more?vid=482145
PubMed

PubMed

TitleDatePubMed
Oligonucleotides as inhibitors of protein synthesis.
2001
Eight novel LDL receptor gene mutations among patients under LDL apheresis in Dresden and Leipzig.
2001
Remodeling of the vessel wall after copper-induced injury is highly attenuated in mice with a total deficiency of plasminogen activator inhibitor-1.
2001 Jan
Identification of a gene, ABCG5, important in the regulation of dietary cholesterol absorption.
2001 Jan
Screening family members at high risk for coronary disease. Why isn't it done?
2001 Jan
Frequency of the R3500Q mutation of the apolipoprotein B-100 gene in a sample screened clinically for familial hypercholesterolemia in Hungary.
2001 Jan
Remnant-like particle (RLP) cholesterol is an independent cardiovascular disease risk factor in women: results from the Framingham Heart Study.
2001 Jan
Plasma lipids and cardiovascular risk: a POSCH report. Program on the Surgical Control of the Hyperlipidemias.
2001 Jan
The effect of a garlic preparation on plasma lipid levels in moderately hypercholesterolemic adults.
2001 Jan
Elevated plasma levels of free-form of TFPI antigen in hypercholesterolemic patients.
2001 Jan
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.
2001 Jan
Essential role for the (hepatic) LDL receptor in macrophage apolipoprotein E-induced reduction in serum cholesterol levels and atherosclerosis.
2001 Jan
Raloxifene and estrogen reduces progression of advanced atherosclerosis--a study in ovariectomized, cholesterol-fed rabbits.
2001 Jan
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.
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
17beta-estradiol, gender independently, reduces atheroma development but not neointimal proliferation after balloon injury in the rabbit aorta.
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
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 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
The role of PPAR-gamma in macrophage differentiation and cholesterol uptake.
2001 Jan
Resolution of alcohols by cholesterol oxidase fromRrhodococcus erythropolis: lack of enantiospecificity for the steroids.
2001 Jan
Effect of lipid reduction on the progression of renal disease: a meta-analysis.
2001 Jan
Accumulation of cholesterol with age in human Bruch's membrane.
2001 Jan
Magnetic resonance imaging and spectroscopic changes in brains of patients with cerebrotendinous xanthomatosis.
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
Dexamethasone inhibits luteinizing hormone-induced synthesis of steroidogenic acute regulatory protein in cultured rat preovulatory follicles.
2001 Jan
Meiosis-activating sterol and the maturation of isolated mouse oocytes.
2001 Jan
Body mass index and metabolic risk factors for coronary heart disease in women.
2001 Jan
Maternal hypercholesterolemia during pregnancy influences the later development of atherosclerosis: clinical and pathogenic implications.
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
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
Pharmacological profile of F 12511, (S)-2',3', 5'-trimethyl-4'-hydroxy-alpha-dodecylthioacetanilide a powerful and systemic acylcoenzyme A: cholesterol acyltransferase inhibitor.
2001 Jan 1
Amyloid-beta is an antioxidant for lipoproteins in cerebrospinal fluid and plasma.
2001 Jan 1
Hydroxy-methylglutaryl-coenzyme A reductase inhibition promotes endothelial nitric oxide synthase activation through a decrease in caveolin abundance.
2001 Jan 2
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
Women's Healthy Lifestyle Project: A randomized clinical trial: results at 54 months.
2001 Jan 2
Cracking down on caveolin: role of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors in modulating edothelial cell nitric oxide production.
2001 Jan 2
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 Jan 3
Estrogen, selective estrogen receptor modulation, and coronary heart disease: something or nothing.
2001 Jan 3
Glycated haemoglobin, diabetes, and mortality in men in Norfolk cohort of european prospective investigation of cancer and nutrition (EPIC-Norfolk).
2001 Jan 6
Cholesterol reduction and non-illness mortality: meta-analysis of randomised clinical trials.
2001 Jan 6
Patents

Patents

05219733
2
05420028
1
06846915
2
06861410
1
07641911
1
07718189
1
07754204
1
07956029
1
08465542
1
08524274
1
08552069
1
20010000151
1

Sample Use Guides

In Vivo Use Guide
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 Wed Jul 05 22:51:53 UTC 2023
Edited
by admin
on Wed Jul 05 22:51:53 UTC 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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DSLD 195 (Number of products:6032)
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Code System Code Type Description
ECHA (EC/EINECS)
200-353-2
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
HSDB
7106
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
CHEBI
16113
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
WIKIPEDIA
CHOLESTEROL
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
DAILYMED
97C5T2UQ7J
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
NSC
8798
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
DRUG BANK
DB04540
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
SMS_ID
100000078528
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
MERCK INDEX
M3478
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY Merck Index
CAS
57-88-5
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL112570
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PRIMARY
NCI_THESAURUS
C369
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PRIMARY
PUBCHEM
5997
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022401
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
FDA UNII
97C5T2UQ7J
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
MESH
D002784
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
EVMPD
SUB12480MIG
Created by admin on Wed Jul 05 22:51:53 UTC 2023 , Edited by admin on Wed Jul 05 22:51:53 UTC 2023
PRIMARY
RS_ITEM_NUM
1131960
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY
RXCUI
2438
Created by admin on Wed Jul 05 22:51:54 UTC 2023 , Edited by admin on Wed Jul 05 22:51:54 UTC 2023
PRIMARY RxNorm
Related Record Type Details
CHOLESTEROL 24-HYDROXYLASE
METABOLIC ENZYME -> SUBSTRATE
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 1
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 27A1
METABOLIC ENZYME -> SUBSTRATE
Structure of CHOLESTEROL, H-3
LABELED -> NON-LABELED
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
ATP-BINDING CASSETTE SUB-FAMILY A MEMBER 1
TRANSPORTER -> SUBSTRATE
CHOLESTEROL SIDE-CHAIN CLEAVAGE ENZYME, MITOCHONDRIAL
METABOLIC ENZYME -> SUBSTRATE
CHOLESTEROL 7-ALPHA-MONOOXYGENASE
METABOLIC ENZYME -> SUBSTRATE
CHOLESTEROL 7-ALPHA-MONOOXYGENASE
METABOLIC ENZYME -> SUBSTRATE
Structure of HYZETIMIBE
INHIBITOR OF ABSORPTION->TARGET
Structure of EZETIMIBE
INHIBITOR OF ABSORPTION->TARGET
Related Record Type Details
Structure of COPROSTANONE
METABOLITE -> PARENT
Structure of 24-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
In human brain
Structure of CHOLEST-5-ENE-3.BETA.,26-DIOL, (25R)-
METABOLITE -> PARENT
PREDOMINANTLY METABOLIZED IN MACROPHAGES
MAJOR
Structure of Pregnenolone
METABOLITE -> PARENT
In steroidogenic tissues
Structure of 4.BETA.-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
Structure of 7.ALPHA.-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
Related Record Type Details
Structure of CHOLESTEROL
ACTIVE MOIETY
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