Explore a selection of our essential drug information below, or:
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 ACholine-phosphate cytidylyltransferase B activatorHumans 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 774 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Smith Lemli Opitz Syndrome 1 somestatus stop reason just information to hide Not Available Completed Screening Glaucoma 1 somestatus stop reason just information to hide Not Available Completed Screening Other Diseases or Conditions 1 somestatus stop reason just information to hide Not Available Not Yet Recruiting Treatment Acute Coronary Syndrome (ACS) / Non-STEMI Acute Coronary Syndrome 1 somestatus stop reason just information to hide Not Available Suspended Basic Science Cholesterol, HDL / Cholesteryl Ester Transfer Protein (CETP) Deficiency / Inborn errors of lipid metabolism / LCAT Deficiency / Tangier Disease 1 somestatus stop reason just information to hide
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
- Yes
- Actions
- Activator
- General Function
- Catalyzes the key rate-limiting step in the CDP-choline pathway for phosphatidylcholine biosynthesis
- Specific Function
- choline-phosphate cytidylyltransferase activity
- Gene Name
- PCYT1B
- Uniprot ID
- Q9Y5K3
- Uniprot Name
- Choline-phosphate cytidylyltransferase B
- Molecular Weight
- 41939.76 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- 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
- Nuclear receptor for calcitriol, the active form of vitamin D3 which mediates the action of this vitamin on cells (PubMed:10678179, PubMed:15728261, PubMed:16913708, PubMed:28698609, PubMed:37478846). Enters the nucleus upon vitamin D3 binding where it forms heterodimers with the retinoid X receptor/RXR (PubMed:28698609). The VDR-RXR heterodimers bind to specific response elements on DNA and activate the transcription of vitamin D3-responsive target genes (PubMed:28698609). Plays a central role in calcium homeostasis (By similarity). Also functions as a receptor for the secondary bile acid lithocholic acid (LCA) and its metabolites (PubMed:12016314, PubMed:32354638)
- Specific Function
- bile acid nuclear receptor activity
- 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
- Calcium-dependent lectin that acts as a pattern recognition receptor (PRR) of the innate immune system: recognizes damage-associated molecular patterns (DAMPs) of abnormal self and pathogen-associated molecular patterns (PAMPs) of bacteria and fungi (PubMed:18509109, PubMed:23602766). The PAMPs notably include mycobacterial trehalose 6,6'-dimycolate (TDM), a cell wall glycolipid with potent adjuvant immunomodulatory functions (PubMed:23602766, PubMed:24101491). Interacts with signaling adapter Fc receptor gamma chain/FCER1G to form a functional complex in myeloid cells (By similarity). Binding of mycobacterial trehalose 6,6'-dimycolate (TDM) to this receptor complex leads to phosphorylation of the immunoreceptor tyrosine-based activation motif (ITAM) of FCER1G, triggering activation of SYK, CARD9 and NF-kappa-B, consequently driving maturation of antigen-presenting cells and shaping antigen-specific priming of T-cells toward effector T-helper 1 and T-helper 17 cell subtypes (By similarity). Also recognizes alpha-mannose residues on pathogenic fungi of the genus Malassezia and mediates macrophage activation (By similarity). Through recognition of DAMPs released upon nonhomeostatic cell death, enables immune sensing of damaged self and promotes inflammatory cell infiltration into the damaged tissue (By similarity)
- Specific Function
- calcium ion 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
- 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 development, cellular differentiation, immunity, circadian rhythm as well as lipid, steroid, xenobiotics and glucose metabolism. Considered to have intrinsic transcriptional activity, have some natural ligands like oxysterols that act as agonists (25-hydroxycholesterol) or inverse agonists (7-oxygenated sterols), enhancing or repressing the transcriptional activity, respectively. Recruits distinct combinations of cofactors to target genes regulatory regions to modulate their transcriptional expression, depending on the tissue, time and promoter contexts. Regulates genes involved in photoreceptor development including OPN1SW, OPN1SM and ARR3 and skeletal muscle development with MYOD1. Required for proper cerebellum development (PubMed:29656859). Regulates SHH gene expression, among others, to induce granule cells proliferation as well as expression of genes involved in calcium-mediated signal transduction. Regulates the circadian expression of several clock genes, including CLOCK, BMAL1, NPAS2 and CRY1. Competes with NR1D1 for binding to their shared DNA response element on some clock genes such as BMAL1, CRY1 and NR1D1 itself, resulting in NR1D1-mediated repression or RORA-mediated activation of clock genes expression, leading to the circadian pattern of clock genes expression. Therefore influences the period length and stability of the clock. Regulates genes involved in lipid metabolism such as apolipoproteins APOA1, APOA5, APOC3 and PPARG. In liver, has specific and redundant functions with RORC as positive or negative modulator of expression of genes encoding phase I and phase II proteins involved in the metabolism of lipids, steroids and xenobiotics, such as CYP7B1 and SULT2A1. Induces a rhythmic expression of some of these genes. In addition, interplays functionally with NR1H2 and NR1H3 for the regulation of genes involved in cholesterol metabolism. Also involved in the regulation of hepatic glucose metabolism through the modulation of G6PC1 and PCK1. In adipose tissue, plays a role as negative regulator of adipocyte differentiation, probably acting through dual mechanisms. May suppress CEBPB-dependent adipogenesis through direct interaction and PPARG-dependent adipogenesis through competition for DNA-binding. Downstream of IL6 and TGFB and synergistically with RORC isoform 2, is implicated in the lineage specification of uncommitted CD4(+) T-helper (T(H)) cells into T(H)17 cells, antagonizing the T(H)1 program. Probably regulates IL17 and IL17F expression on T(H) by binding to the essential enhancer conserved non-coding sequence 2 (CNS2) in the IL17-IL17F locus. Involved in hypoxia signaling by interacting with and activating the transcriptional activity of HIF1A. May inhibit cell growth in response to cellular stress. May exert an anti-inflammatory role by inducing CHUK expression and inhibiting NF-kappa-B signaling
- Specific Function
- beta-catenin binding
- 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
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- 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
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- 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 August 26, 2024 19:22