coumarin (PAMDB120466)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120466
Identification
Name: coumarin
Description:A chromenone having the keto group located at the 2-position.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1,2-Benzopyrone
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone
  • 2H-1-Benzopyran-2-one
  • 2H-benzo[b]pyran-2-one
  • 5,6-Benzo-2-pyrone
  • Benzo-a-pyrone
  • Benzo-alpha-pyrone
  • cis-o-Coumarinic acid lactone
  • Coumarine
  • Coumarine
  • Coumarinic anhydride
  • Cumarin
  • o-hydroxycinnamic acid δ-lactone
  • o-Hydroxycinnamic acid lactone
  • Rattex
  • Tonka bean camphor
Chemical Formula: C9H6O2
Average Molecular Weight: 146.145
Monoisotopic Molecular Weight: 146.03677
InChI Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
InChI:InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
CAS number: 91-64-5
IUPAC Name:2H-chromen-2-one
Traditional IUPAC Name: coumarin
SMILES:C1(OC2(=CC=CC=C(C=C1)2))=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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 Chemical entities
Super ClassOrganic compounds
Class Phenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct Parent Coumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 71 °C
Experimental Properties:
PropertyValueReference
Melting Point71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9 mg/mLNot Available
LogP2.23Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.0 mg/mLALOGPS
logP1.72ALOGPS
logP1.78ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.55 m3·mol-1ChemAxon
Polarizability14.36 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Hydrogen ion + coumarinate → coumarin + Water
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-MSsplash10-014v-6900000000-3e901733dc003512f338View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-6ef9288c71771dd56774View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-93154d9b40c4d0fdd1aeView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-72ec22913d1d574be75bView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7L) , Positivesplash10-00kb-8900000000-89e86d11a0dc2841af42View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014i-7900000000-25bab36f91f71ac65817View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-02tj-9600000000-6e4062e14fc72534c96aView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e5519a8faf9232fc0fccView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a6dc6c6c3032891bd134View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4900000000-139cc9674e0b2836e441View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e1154242f99d56bc5ed4View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d6df7c01bbecf91182c9View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-961e88f9b351b2d27becView in MoNA
    MSMass Spectrum (Electron Ionization)splash10-00kb-9700000000-7a649c1e257a7ad17b9dView in MoNA
    1D NMR1H NMR SpectrumNot Available
    1D NMR1H NMR SpectrumNot Available
    1D NMR13C NMR SpectrumNot Available
    2D NMR[1H,13C] 2D NMR SpectrumNot Available
    References
    References:
    • Vocanson M, Valeyrie M, Rozières A, Hennino A, Floc'h F, Gard A, Nicolas JF (2007)Lack of evidence for allergenic properties of coumarin in a fragrance allergy mouse model. Contact dermatitis 57, Pubmed: 17988284
    • Abraham K, Pfister M, Wöhrlin F, Lampen A (2011)Relative bioavailability of coumarin from cinnamon and cinnamon-containing foods compared to isolated coumarin: a four-way crossover study in human volunteers. Molecular nutrition & food research 55, Pubmed: 21462332
    • Marcolan M, Martins PA, Pedrosa VA, Rodrigues MR, de Oliveira HP, Codognoto L (2011)Spectrofluorimetric determination of coumarin in commercial tablets. Journal of fluorescence 21, Pubmed: 21046436
    • Coltro WK, Lunte SM, Carrilho E (2008)Comparison of the analytical performance of electrophoresis microchannels fabricated in PDMS, glass, and polyester-toner. Electrophoresis 29, Pubmed: 19025869
    • Weigt S, Huebler N, Strecker R, Braunbeck T, Broschard TH (2012)Developmental effects of coumarin and the anticoagulant coumarin derivative warfarin on zebrafish (Danio rerio) embryos. Reproductive toxicology (Elmsford, N.Y.) 33, Pubmed: 21798343
    • Krasteva M, Peguet-Navarro J, Moulon C, Courtellemont P, Redziniak G, Schmitt D (1996)In vitro primary sensitization of hapten-specific T cells by cultured human epidermal Langerhans cells--a screening predictive assay for contact sensitizers. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 26, Pubmed: 8735869
    Synthesis Reference: Huang, Zhong-jing. Synthesis of coumarin under microwave irradiation. Guangxi Huagong (2001), 30(3), 1-2.
    Material Safety Data Sheet (MSDS) Download (PDF)
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC28794
    HMDBHMDB01218
    DRUGBANKDB04665
    CHEMSPIDER13848793
    PUBCHEM323
    CHEBI28794
    LIGAND-CPDC05851