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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:34 UTC
Update Date2018-03-12 22:08:20 UTC
HMDB IDHMDB0031805
Secondary Accession Numbers
  • HMDB31805
Metabolite Identification
Common Name(E)-Monocrotophos
Description(e)-Monocrotophos, also known as azodrin or nuvacron, belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain (e)-Monocrotophos exists as a solid, slightly soluble (in water), and an extremely weak acidic (essentially neutral) compound (based on its pKa). Within the cell, (e)-monocrotophos is primarily located in the cytoplasm (e)-Monocrotophos is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(e)-MonocrotophosChEBI
AzodrinChEBI
Dimethyl (e)-1-methyl-2-(methylcarbamoyl)vinyl phosphateChEBI
Dimethyl (e)-3-hydroxy-N-methylcrotonamideChEBI
Phosphoric acid, dimethyl (e)-1-methyl-3-(methylamino)-3-oxo-1-propenyl esterChEBI
Dimethyl (e)-1-methyl-2-(methylcarbamoyl)vinyl phosphoric acidGenerator
Phosphate, dimethyl (e)-1-methyl-3-(methylamino)-3-oxo-1-propenyl esterGenerator
3-(Dimethoxyphosphinyloxy)N-methyl-cis-crotonamideHMDB
3-Dimethoxyphosphinoyloxy-N-methylisocrotonamideHMDB
3-Hydroxy-N-methyl-cis-crotonamide dimethyl phosphateHMDB
3-Hydroxy-N-methyl-cis-crotonamide dimethyl phosphate esterHMDB
3-Hydroxy-N-methyl-dimethylphosphate(e)-crotonamideHMDB
3-Hydroxy-N-methyl-dimethylphosphatecis-crotonamideHMDB
AimocronHMDB
ApadrinHMDB
AzadrinHMDB
Azodrin 202RHMDB
Azodrin insecticideHMDB
Azodrin-71HMDB
BilobornHMDB
BilobranHMDB
cis-1-Methyl-2-methyl carbamoyl vinyl phosphateHMDB
CorophosHMDB
CrisodinHMDB
CrisodrinHMDB
Croton 36HMDB
CrotosHMDB
Des-N-methyl dicrotophosHMDB
Dimethyl 1-methyl-2-(methylcarbamoyl)vinyl phosphate, cisHMDB
Dimethyl phosphate OF 3-hydroxy-N-methyl-cis-crotonamideHMDB
e-MonocrotophosHMDB
Glore phos 36HMDB
HazodrinHMDB
MonocilHMDB
Monocil 40HMDB
MonocronHMDB
Monocrotophos 40 ecHMDB
MonodrinHMDB
MonokrotofoszHMDB
MonostarHMDB
N-Desmethyl bidrinHMDB
NuvacronHMDB
Nuvacron 20HMDB
Nuvacron-20HMDB
O,O-Dimethyl cis-1-methyl-2-methylcarbamoylvinylphosphateHMDB
O,O-Dimethyl-O-(2-N-methylcarbamoyl-1-methyl-vinyl)-fosfaatHMDB
O,O-Dimetil-O-(2-N-metilcarbamoil-1-metil-vinil)-fosfatoHMDB
PandarHMDB
ParryfosHMDB
PillardrinHMDB
PlantdrinHMDB
Rapid XHMDB
Shell SD 9129HMDB
SusvinHMDB
UlvairHMDB
Chemical FormulaC7H14NO5P
Average Molecular Weight223.1635
Monoisotopic Molecular Weight223.060959075
IUPAC Name(2E)-3-[(dimethoxyphosphoryl)oxy]-N-methylbut-2-enamide
Traditional Namemonocrotophos
CAS Registry Number6923-22-4
SMILES
CNC(=O)\C=C(/C)OP(=O)(OC)OC
InChI Identifier
InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+
InChI KeyKRTSDMXIXPKRQR-AATRIKPKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentDialkyl phosphates
Alternative Parents
Substituents
  • Dialkyl phosphate
  • Organic phosphate
  • N-acyl-amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point54 - 55 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.7 g/LALOGPS
logP-0.26ALOGPS
logP-0.47ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)15.73ChemAxon
pKa (Strongest Basic)0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.64 m³·mol⁻¹ChemAxon
Polarizability20.27 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e97ee38f28a0c37d737aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-e97ee38f28a0c37d737aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adi-1910000000-d0a2fd9e1d3db52548cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002f-0900000000-bc93c9f49b96b126240cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-5bef9f97534886d7bbc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-62b02093267f5b04a4c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-c0b68f0a70caf30dde61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-45b4da314919775f4d8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fft-7930000000-7407d8205c3ca4de8df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-9510000000-55fdc29c7e5ebc6c1393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9500000000-fab7d8fe424250861d0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1960000000-1dc3d4bd92c27f7b5848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2910000000-9db8c31b2df0f599540dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9200000000-1386bb26d28d0f9dfa6eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-8900000000-0426bb5e86a7ce455ca3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008479
KNApSAcK IDNot Available
Chemspider ID4522053
KEGG Compound IDC18663
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMonocrotophos
METLIN IDNot Available
PubChem Compound5371562
PDB IDNot Available
ChEBI ID38728
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .