Coumarin
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Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Coumarin
- DrugBank Accession Number
- DB04665
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- 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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ACarbonic anhydrase 4 inhibitorHumans ACarbonic anhydrase 1 inhibitorHumans ACarbonic anhydrase 6 inhibitorHumans ACarbonic anhydrase 9 inhibitorHumans ACarbonic anhydrase 14 inhibitorHumans ACarbonic anhydrase 2 inhibitorHumans ACarbonic anhydrase 12 inhibitorHumans 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
- 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 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 … show 1 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 Ischemic Stroke 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Venous Insufficiency (CVI) 1 somestatus stop reason just information to hide 4 Completed Treatment Deep Vein Thrombosis / Pulmonary Embolism 1 somestatus stop reason just information to hide 1 Completed Treatment Hypertriglyceridemias 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
- 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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1. DetailsCarbonic anhydrase 4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide into bicarbonate and protons and thus is essential to maintaining intracellular and extracellular pH (PubMed:15563508, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17652713, PubMed:17705204, PubMed:18618712, PubMed:19186056, PubMed:19206230, PubMed:7625839). May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis (PubMed:15563508). It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid (PubMed:15563508)
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA4
- Uniprot ID
- P22748
- Uniprot Name
- Carbonic anhydrase 4
- Molecular Weight
- 35032.075 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]
2. DetailsCarbonic anhydrase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide (PubMed:10550681, PubMed:16506782, PubMed:16686544, PubMed:16807956, PubMed:17127057, PubMed:17314045, PubMed:17407288, PubMed:18618712, PubMed:19186056, PubMed:19206230). Can hydrate cyanamide to urea (PubMed:10550681)
- Specific Function
- arylesterase activity
- Gene Name
- CA1
- Uniprot ID
- P00915
- Uniprot Name
- Carbonic anhydrase 1
- Molecular Weight
- 28870.0 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]
3. DetailsCarbonic anhydrase 6
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide. Its role in saliva is unknown
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA6
- Uniprot ID
- P23280
- Uniprot Name
- Carbonic anhydrase 6
- Molecular Weight
- 35366.615 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]
4. DetailsCarbonic anhydrase 9
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the interconversion between carbon dioxide and water and the dissociated ions of carbonic acid (i.e. bicarbonate and hydrogen ions)
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA9
- Uniprot ID
- Q16790
- Uniprot Name
- Carbonic anhydrase 9
- Molecular Weight
- 49697.36 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]
5. DetailsCarbonic anhydrase 14
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA14
- Uniprot ID
- Q9ULX7
- Uniprot Name
- Carbonic anhydrase 14
- Molecular Weight
- 37667.37 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]
6. DetailsCarbonic anhydrase 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the reversible hydration of carbon dioxide (PubMed:11327835, PubMed:11802772, PubMed:11831900, PubMed:12056894, PubMed:12171926, PubMed:1336460, PubMed:14736236, PubMed:15300855, PubMed:15453828, PubMed:15667203, PubMed:15865431, PubMed:16106378, PubMed:16214338, PubMed:16290146, PubMed:16686544, PubMed:16759856, PubMed:16807956, PubMed:17127057, PubMed:17251017, PubMed:17314045, PubMed:17330962, PubMed:17346964, PubMed:17540563, PubMed:17588751, PubMed:17705204, PubMed:18024029, PubMed:18162396, PubMed:18266323, PubMed:18374572, PubMed:18481843, PubMed:18618712, PubMed:18640037, PubMed:18942852, PubMed:1909891, PubMed:1910042, PubMed:19170619, PubMed:19186056, PubMed:19206230, PubMed:19520834, PubMed:19778001, PubMed:7761440, PubMed:7901850, PubMed:8218160, PubMed:8262987, PubMed:8399159, PubMed:8451242, PubMed:8485129, PubMed:8639494, PubMed:9265618, PubMed:9398308). Can also hydrate cyanamide to urea (PubMed:10550681, PubMed:11015219). Stimulates the chloride-bicarbonate exchange activity of SLC26A6 (PubMed:15990874). Essential for bone resorption and osteoclast differentiation (PubMed:15300855). Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption
- Specific Function
- arylesterase activity
- Gene Name
- CA2
- Uniprot ID
- P00918
- Uniprot Name
- Carbonic anhydrase 2
- Molecular Weight
- 29245.895 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]
7. DetailsCarbonic anhydrase 12
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Reversible hydration of carbon dioxide
- Specific Function
- carbonate dehydratase activity
- Gene Name
- CA12
- Uniprot ID
- O43570
- Uniprot Name
- Carbonic anhydrase 12
- Molecular Weight
- 39450.615 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]
8. DetailsCytochrome P450 2A6
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
Enzymes
1. DetailsCytochrome P450 2C9
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- 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 August 26, 2024 19:22