Identification
NameCoumarin
Accession NumberDB04665
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
1,2-benzopyrone
2H-1-benzopyran-2-one
2H-benzo(b)pyran-2-one
Coumarinic lactone
Cumarin
External IDs NSC-8774
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIA4VZ22K1WT
CAS number91-64-5
WeightAverage: 146.1427
Monoisotopic: 146.036779436
Chemical FormulaC9H6O2
InChI KeyZYGHJZDHTFUPRJ-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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cytochrome P450 2A6ProteinunknownNot AvailableHumanP11509 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9912
Blood Brain Barrier+0.9565
Caco-2 permeable+0.9155
P-glycoprotein substrateNon-substrate0.6697
P-glycoprotein inhibitor INon-inhibitor0.854
P-glycoprotein inhibitor IINon-inhibitor0.8663
Renal organic cation transporterNon-inhibitor0.8301
CYP450 2C9 substrateNon-substrate0.7966
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.7139
CYP450 1A2 substrateInhibitor0.9117
CYP450 2C9 inhibitorNon-inhibitor0.6943
CYP450 2D6 inhibitorNon-inhibitor0.9105
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8115
Ames testNon AMES toxic0.887
CarcinogenicityNon-carcinogens0.9412
BiodegradationReady biodegradable0.5884
Rat acute toxicity2.4622 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8702
hERG inhibition (predictor II)Non-inhibitor0.9474
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-014v-6900000000-3e901733dc003512f338View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00kb-8900000000-89e86d11a0dc2841af42View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-7900000000-25bab36f91f71ac65817View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-02tj-9600000000-4a54f8d648a87a9c5811View 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
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-9200000000-38161abf759afe5aa970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-c06b97954c5a847401e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-1900000000-6f05165347e6221503b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6x-8900000000-6e9532ad6b20b76b3d4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9300000000-3f95abb339f5c1aea790View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9200000000-c404268b480236aaf197View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6x-9500000000-da852779b618f093b767View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9300000000-c29bd55b8ca9510aec2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9100000000-161d49edf4310e8a785cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-3777f28f5438e1f09160View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-bfe432f57faff8d62318View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-0000800900-d301ec3931fa0374d57aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0690-7900000000-975e23de8283da2b67baView 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
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).
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct ParentCoumarins and derivatives
Alternative Parents1-benzopyrans / Pyranones and derivatives / Benzenoids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsCoumarin / 1-benzopyran / Benzopyran / Pyranone / Benzenoid / Pyran / Heteroaromatic compound / Lactone / Oxacycle / Organoheterocyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorscoumarins (CHEBI:28794 ) / coumarins, Phenylpropanoids (C05851 ) / a coumarin (COUMARIN )

Targets

Kind
Protein
Organism
Human
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Uniprot Name:
Cytochrome P450 2A6
Molecular Weight:
56501.005 Da
Drug created on September 11, 2007 11:49 / Updated on June 23, 2017 10:18