Identification
- Generic Name
- Cholesterol
- DrugBank Accession Number
- DB04540
- Background
The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cholesterol (DB04540)
- Weight
- Average: 386.6535
Monoisotopic: 386.354866094 - Chemical Formula
- C27H46O
- Synonyms
- (3β,14β,17α)-cholest-5-en-3-ol
- Cholest-5-en-3beta-ol
- Cholesterin
- Cholesterol
- External IDs
- NSC-8798
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNuclear receptor subfamily 1 group I member 3 Not Available Humans UVitamin D3 receptor Not Available Humans UC-type lectin domain family 4 member E ligandHumans UNuclear receptor ROR-alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib Cholesterol may increase the excretion rate of Abemaciclib which could result in a lower serum level and potentially a reduction in efficacy. Afatinib Cholesterol may increase the excretion rate of Afatinib which could result in a lower serum level and potentially a reduction in efficacy. Allopurinol Cholesterol may increase the excretion rate of Allopurinol which could result in a lower serum level and potentially a reduction in efficacy. Alpelisib Cholesterol may increase the excretion rate of Alpelisib which could result in a lower serum level and potentially a reduction in efficacy. Apixaban Cholesterol may increase the excretion rate of Apixaban which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Cholestane steroids
- Direct Parent
- Cholesterols and derivatives
- Alternative Parents
- 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cholesterol / Cholesterol-skeleton / Cyclic alcohol / Delta-5-steroid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- cholestanoid, 3beta-sterol (CHEBI:16113) / cholestane, Cholesterol and derivatives, Cholestane and derivatives (C00187) / Cholesterol and derivatives (LMST01010001)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 97C5T2UQ7J
- CAS number
- 57-88-5
- InChI Key
- HVYWMOMLDIMFJA-DPAQBDIFSA-N
- InChI
- 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
- IUPAC Name
- (1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
- 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
References
- Synthesis Reference
Tatu Miettenen, Ingmar Wester, Hannu Vanhanen, "Substance for lowering high cholesterol level in serum and methods for preparing and using the same." U.S. Patent US6174560, issued February, 1944.
US6174560- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000067
- KEGG Drug
- D00040
- KEGG Compound
- C00187
- PubChem Compound
- 5997
- PubChem Substance
- 46508234
- ChemSpider
- 5775
- BindingDB
- 20192
- 2438
- ChEBI
- 16113
- ChEMBL
- CHEMBL112570
- ZINC
- ZINC000003875383
- PDBe Ligand
- CLR
- Wikipedia
- Cholesterol
- PDB Entries
- 1lri / 1n83 / 1zhy / 2rh1 / 2zxe / 3a3y / 3am6 / 3d4s / 3gki / 3jd8 … show 649 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Cardiovascular Disease (CVD) / Carotid Atherosclerosis / Diabetes / Hyperlipidemias / Hypertension 1 3 Completed Treatment High Cholesterol 1 3 Recruiting Treatment Acute Coronary Syndrome (ACS) 1 2 Recruiting Treatment Cone Rod Dystrophy / Hearing loss or impairment / Smith Lemli Opitz Syndrome 1 1 Completed Treatment Actinic Porokeratosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 148.5 °C PhysProp boiling point (°C) 360 °C PhysProp water solubility 0.095 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 2.79e-05 mg/mL ALOGPS logP 7.02 ALOGPS logP 7.11 Chemaxon logS -7.1 ALOGPS pKa (Strongest Acidic) 18.2 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 120.62 m3·mol-1 Chemaxon Polarizability 50.64 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9749 Caco-2 permeable + 0.8184 P-glycoprotein substrate Substrate 0.6477 P-glycoprotein inhibitor I Inhibitor 0.6404 P-glycoprotein inhibitor II Non-inhibitor 0.529 Renal organic cation transporter Non-inhibitor 0.7691 CYP450 2C9 substrate Non-substrate 0.8257 CYP450 2D6 substrate Non-substrate 0.8794 CYP450 3A4 substrate Substrate 0.7439 CYP450 1A2 substrate Non-inhibitor 0.9355 CYP450 2C9 inhibitor Non-inhibitor 0.9194 CYP450 2D6 inhibitor Non-inhibitor 0.9519 CYP450 2C19 inhibitor Non-inhibitor 0.9177 CYP450 3A4 inhibitor Non-inhibitor 0.8638 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6721 Ames test Non AMES toxic 0.8888 Carcinogenicity Non-carcinogens 0.932 Biodegradation Not ready biodegradable 0.9825 Rat acute toxicity 2.8078 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.773 hERG inhibition (predictor II) Non-inhibitor 0.7552
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 222.2272632 predictedDarkChem Lite v0.1.0 [M-H]- 203.1975632 predictedDarkChem Lite v0.1.0 [M-H]- 213.1418632 predictedDarkChem Lite v0.1.0 [M-H]- 204.02931 predictedDeepCCS 1.0 (2019) [M+H]+ 222.5553632 predictedDarkChem Lite v0.1.0 [M+H]+ 204.0645632 predictedDarkChem Lite v0.1.0 [M+H]+ 212.0801632 predictedDarkChem Lite v0.1.0 [M+H]+ 205.92358 predictedDeepCCS 1.0 (2019) [M+Na]+ 221.6720632 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.4945632 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.6860632 predictedDarkChem Lite v0.1.0 [M+Na]+ 211.5294 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
- Gene Name
- NR1I3
- Uniprot ID
- Q14994
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 3
- Molecular Weight
- 39942.145 Da
References
- Mooijaart SP, Brandt BW, Baldal EA, Pijpe J, Kuningas M, Beekman M, Zwaan BJ, Slagboom PE, Westendorp RG, van Heemst D: C. elegans DAF-12, Nuclear Hormone Receptors and human longevity and disease at old age. Ageing Res Rev. 2005 Aug;4(3):351-71. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
- Gene Name
- VDR
- Uniprot ID
- P11473
- Uniprot Name
- Vitamin D3 receptor
- Molecular Weight
- 48288.64 Da
References
- Mooijaart SP, Brandt BW, Baldal EA, Pijpe J, Kuningas M, Beekman M, Zwaan BJ, Slagboom PE, Westendorp RG, van Heemst D: C. elegans DAF-12, Nuclear Hormone Receptors and human longevity and disease at old age. Ageing Res Rev. 2005 Aug;4(3):351-71. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Ligand
- General Function
- C-type lectin that functions as cell-surface receptor for a wide variety of ligands such as damaged cells, fungi and mycobacteria. Plays a role in the recognition of pathogenic fungi, such as Candida albicans. The detection of mycobacteria is via trehalose 6,6'-dimycolate (TDM), a cell wall glycolipid. Specifically recognizes alpha-mannose residues on pathogenic fungi of the genus Malassezia. Recognizes also SAP130, a nuclear protein, that is released by dead or dying cells. Transduces signals through an ITAM-containing adapter protein, Fc receptor gamma chain /FCER1G. Induces secretion of inflammatory cytokines through a pathway that depends on SYK, CARD9 and NF-kappa-B.
- Specific Function
- Carbohydrate binding
- Gene Name
- CLEC4E
- Uniprot ID
- Q9ULY5
- Uniprot Name
- C-type lectin domain family 4 member E
- Molecular Weight
- 25072.31 Da
References
- Kiyotake R, Oh-Hora M, Ishikawa E, Miyamoto T, Ishibashi T, Yamasaki S: Human Mincle Binds to Cholesterol Crystals and Triggers Innate Immune Responses. J Biol Chem. 2015 Oct 16;290(42):25322-32. doi: 10.1074/jbc.M115.645234. Epub 2015 Aug 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Key regulator of embryonic ...
- Gene Name
- RORA
- Uniprot ID
- P35398
- Uniprot Name
- Nuclear receptor ROR-alpha
- Molecular Weight
- 58974.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Wang E, Casciano CN, Clement RP, Johnson WW: Cholesterol interaction with the daunorubicin binding site of P-glycoprotein. Biochem Biophys Res Commun. 2000 Oct 5;276(3):909-16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51