Showing Compound Card for Coumaphos (CDB006256)

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Record Information
Version1.0
Created at2020-07-28 20:23:11 UTC
Updated at2020-11-18 16:40:16 UTC
CannabisDB IDCDB006256
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCoumaphos
DescriptionCoumaphos, also known as meldane or asuntol, 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). Based on a literature review a significant number of articles have been published on Coumaphos.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioateChEBI
3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid esterChEBI
3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarinChEBI
3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioateChEBI
O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphateChEBI
O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioateChEBI
O-(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphateChEBI
Phosphorothioic acid, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl esterChEBI
MeldaneKegg
3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioic acidGenerator
3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphate esterGenerator
3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioic acidGenerator
O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphoric acidGenerator
O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioic acidGenerator
O-(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphoric acidGenerator
Phosphorothioate, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl esterGenerator
AsuntolMeSH
CoumafosMeSH
Chemical FormulaC14H16ClO5PS
Average Molecular Weight362.766
Monoisotopic Molecular Weight362.014458531
IUPAC NameO-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate
Traditional Namemeldane
CAS Registry Number56-72-4
SMILES
CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2
InChI Identifier
InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3
InChI KeyBXNANOICGRISHX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Aryl thiophosphate
  • Benzopyran
  • 1-benzopyran
  • Thiophosphate triester
  • Pyranone
  • Aryl chloride
  • Aryl halide
  • Thiophosphoric acid ester
  • Benzenoid
  • Organic thiophosphoric acid or derivatives
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.5ALOGPS
logP4.15ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.93 m³·mol⁻¹ChemAxon
Polarizability34.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-06vj-7954000000-80e126f971975f223e602014-09-20View Spectrum
Predicted GC-MSCoumaphos, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCoumaphos, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0009000000-1eb96120bb8c3511912e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bw9-0039000000-13c6f9257fbc11ac58782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0091000000-5f535054f0f4f1d401672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-c875939d86ddad0a8e082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0590000000-878fbf88eb9b1468b0022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-0590000000-878fbf88eb9b1468b0022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-002b-6690000000-0b075949b4fc64417b452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002b-3930000000-afb7f841e4d8f9374a102021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-004j-6690000000-e4dbfc7cf2aa396974cb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-05ecad535abaa608b26f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0002-5900000000-87869720e427b6ae2f4d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0091000000-fa3c3a4750e37d9433012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-0590000000-89c84cbf0e4cff0420d32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-03di-0209000000-b115f399660285d47a7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0002-7491000000-17d6540e989451a469d42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-056r-1396000000-1b6df76eac4b3635ae592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0bw9-0039000000-13c6f9257fbc11ac58782021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0091000000-6939f400c7b0e01353142021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-5fe0783ca5e8f6cf5a522021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0009000000-803a80ca33dda23dc6aa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu0-1129000000-00264c0e462527baf3112016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hkm-4940000000-213ceacd491055ba0ef52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-0129000000-a5bf355fe65815e55f3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0229000000-ba2d0f5d2138ff62e8012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-0968000000-a999b49b42dee23cdc872016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0250488
DrugBank IDDB11390
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2768
KEGG Compound IDC11025
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoumaphos
METLIN IDNot Available
PubChem Compound2871
PDB IDNot Available
ChEBI ID3903
References
General References
  1. Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. [PubMed:29843862 ]