Identification
- Generic Name
- Coumarin
- DrugBank Accession Number
- DB04665
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Coumarin (DB04665)
- Weight
- Average: 146.1427
Monoisotopic: 146.036779436 - Chemical Formula
- C9H6O2
- Synonyms
- 1,2-benzopyrone
- 2H-1-benzopyran-2-one
- 2H-benzo(b)pyran-2-one
- Coumarinic lactone
- Cumarin
- External IDs
- NSC-8774
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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 UCytochrome P450 2A6 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- 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
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAbatacept The metabolism of Coumarin can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Coumarin. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Coumarin. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Coumarin. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Coumarin is combined with Acemetacin. - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
- Ensure consistent Vitamin K intake.
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Coumarins and derivatives
- Sub Class
- Not Available
- Direct Parent
- Coumarins and derivatives
- Alternative Parents
- 1-benzopyrans / Pyranones and derivatives / Benzenoids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- coumarins (CHEBI:28794) / coumarins, Phenylpropanoids (C05851) / a coumarin (COUMARIN)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- A4VZ22K1WT
- CAS number
- 91-64-5
- InChI Key
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
- IUPAC Name
- 2H-chromen-2-one
- SMILES
- O=C1OC2=CC=CC=C2C=C1
References
- Synthesis Reference
Ernst-Christian Witte, Peter Neubert, Androniki Roesch, "2H-1-benzopyran-2-one derivatives, processes for the preparation thereof and pharmaceutical compositions containing them." U.S. Patent US4670439, issued May, 1974.
US4670439- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001218
- KEGG Compound
- C05851
- PubChem Compound
- 323
- PubChem Substance
- 46509134
- ChemSpider
- 13848793
- BindingDB
- 12342
- 2898
- ChEBI
- 28794
- ChEMBL
- CHEMBL6466
- ZINC
- ZINC000000074709
- PharmGKB
- PA134521193
- PDBe Ligand
- COU
- Wikipedia
- Coumarin
- PDB Entries
- 1z10 / 2h90 / 2pmj / 2pwb / 3crb / 3l5m / 3l66 / 3l68 / 4uti / 4utl
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Chronic Venous Insufficiency (CVI) 1 4 Completed Treatment Deep Vein Thrombosis / Pulmonary Embolism 1 1 Completed Treatment Hypertriglyceridemias 1 Not Available Completed Not Available Ischemic Stroke 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.0 mg/mL ALOGPS logP 1.72 ALOGPS logP 1.78 Chemaxon logS -2.2 ALOGPS pKa (Strongest Basic) -6.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 26.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 41.55 m3·mol-1 Chemaxon Polarizability 14.36 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9912 Blood Brain Barrier + 0.9565 Caco-2 permeable + 0.9155 P-glycoprotein substrate Non-substrate 0.6697 P-glycoprotein inhibitor I Non-inhibitor 0.854 P-glycoprotein inhibitor II Non-inhibitor 0.8663 Renal organic cation transporter Non-inhibitor 0.8301 CYP450 2C9 substrate Non-substrate 0.7966 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7139 CYP450 1A2 substrate Inhibitor 0.9117 CYP450 2C9 inhibitor Non-inhibitor 0.6943 CYP450 2D6 inhibitor Non-inhibitor 0.9105 CYP450 2C19 inhibitor Non-inhibitor 0.5 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8115 Ames test Non AMES toxic 0.887 Carcinogenicity Non-carcinogens 0.9412 Biodegradation Ready biodegradable 0.5884 Rat acute toxicity 2.4622 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8702 hERG inhibition (predictor II) Non-inhibitor 0.9474
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.1017794 predictedDarkChem Lite v0.1.0 [M-H]- 127.2178794 predictedDarkChem Lite v0.1.0 [M-H]- 126.9930794 predictedDarkChem Lite v0.1.0 [M-H]- 127.930466 predictedDeepCCS 1.0 (2019) [M+H]+ 128.2137794 predictedDarkChem Lite v0.1.0 [M+H]+ 128.2887794 predictedDarkChem Lite v0.1.0 [M+H]+ 128.1407794 predictedDarkChem Lite v0.1.0 [M+H]+ 130.7934 predictedDeepCCS 1.0 (2019) [M+Na]+ 127.5417794 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8572794 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.7646794 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.87288 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
Drug created at September 11, 2007 17:49 / Updated at July 14, 2020 10:58