Coumarin

Identification

Name
Coumarin
Accession Number
DB04665
Type
Small Molecule
Groups
Experimental
Description
Not 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
Categories
UNII
A4VZ22K1WT
CAS number
91-64-5
Weight
Average: 146.1427
Monoisotopic: 146.036779436
Chemical Formula
C9H6O2
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytochrome P450 2A6Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB01218
KEGG Compound
C05851
PubChem Compound
323
PubChem Substance
46509134
ChemSpider
13848793
BindingDB
12342
ChEBI
28794
ChEMBL
CHEMBL6466
PharmGKB
PA134521193
HET
COU
PDB Entries
1z10 / 2h90 / 2pmj / 2pwb / 3crb / 3l5m / 3l66 / 3l68 / 4uti / 4utl

Clinical Trials

Clinical Trials
Not Available

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
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-014v-6900000000-3e901733dc003512f338
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00kb-8900000000-89e86d11a0dc2841af42
GC-MS Spectrum - EI-BGC-MSsplash10-014i-7900000000-25bab36f91f71ac65817
GC-MS Spectrum - EI-BGC-MSsplash10-02tj-9600000000-4a54f8d648a87a9c5811
GC-MS Spectrum - GC-MSGC-MSsplash10-014v-6900000000-3e901733dc003512f338
Mass Spectrum (Electron Ionization)MSsplash10-00kb-9700000000-7a649c1e257a7ad17b9d
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0002-0900000000-6ef9288c71771dd56774
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-93154d9b40c4d0fdd1ae
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014i-9000000000-72ec22913d1d574be75b
MS/MS Spectrum - EI-B (HITACHI RMU-7L) , PositiveLC-MS/MSsplash10-00kb-8900000000-89e86d11a0dc2841af42
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-014i-7900000000-25bab36f91f71ac65817
MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , PositiveLC-MS/MSsplash10-02tj-9600000000-6e4062e14fc72534c96a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-e5519a8faf9232fc0fcc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-a6dc6c6c3032891bd134
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-4900000000-139cc9674e0b2836e441
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-e1154242f99d56bc5ed4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-d6df7c01bbecf91182c9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1900000000-961e88f9b351b2d27bec
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-000i-9200000000-38161abf759afe5aa970
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-c06b97954c5a847401e8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-1900000000-6f05165347e6221503b0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f6x-8900000000-6e9532ad6b20b76b3d4b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-9300000000-3f95abb339f5c1aea790
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-9200000000-c404268b480236aaf197
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f6x-9500000000-da852779b618f093b767
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9300000000-c29bd55b8ca9510aec2f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9100000000-161d49edf4310e8a785c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-3777f28f5438e1f09160
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-bfe432f57faff8d62318
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0089-0000800900-d301ec3931fa0374d57a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0690-7900000000-975e23de8283da2b67ba
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-001i-0900000000-eb06aa4e28f43c98e973
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-0ac49ca1676aa2241ed9
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Coumarin / 1-benzopyran / Benzopyran / Pyranone / Benzenoid / Pyran / Heteroaromatic compound / Lactone / Oxacycle / Organoheterocyclic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
coumarins (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. Const...
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 October 02, 2017 05:37