Record Information
Version1.0
Creation date2010-04-08 22:07:02 UTC
Update date2020-02-24 19:10:54 UTC
Primary IDFDB006215
Secondary Accession Numbers
  • FDB008479
Chemical Information
FooDB NameMomordin
Description(e)-monocrotophos, also known as azodrin or dimethyl (E)-3-hydroxy-N-methylcrotonamide, is a member of the class of compounds known as dialkyl phosphates. Dialkyl phosphates are organic compounds containing a phosphate group that is linked to exactly two alkyl chain (e)-monocrotophos is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Within the cell, (e)-monocrotophos is primarily located in the cytoplasm. It can also be found in the extracellular space (e)-monocrotophos is a non-carcinogenic (not listed by IARC) potentially toxic compound. If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally (T3DB).
CAS Number6923-22-4
Structure
Thumb
Synonyms
SynonymSource
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
(e)-MonocrotophosChEBI
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)-0.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.64 m³·mol⁻¹ChemAxon
Polarizability20.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H14NO5P
IUPAC name(2E)-3-[(dimethoxyphosphoryl)oxy]-N-methylbut-2-enamide
InChI IdentifierInChI=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
Isomeric SMILESCNC(=O)\C=C(/C)OP(=O)(OC)OC
Average Molecular Weight223.1635
Monoisotopic Molecular Weight223.060959075
Classification
Description 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 ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentDialkyl phosphates
Alternative Parents
Substituents
  • Dialkyl phosphate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-8900000000-0426bb5e86a7ce455ca3Spectrum
GC-MSMomordin, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-e97ee38f28a0c37d737aSpectrum
GC-MSMomordin, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-e97ee38f28a0c37d737aSpectrum
Predicted GC-MSMomordin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-1910000000-d0a2fd9e1d3db52548cfSpectrum
Predicted GC-MSMomordin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMomordin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002f-0900000000-bc93c9f49b96b126240cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-5bef9f97534886d7bbc1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-62b02093267f5b04a4c6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-c0b68f0a70caf30dde61Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-45b4da314919775f4d8bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-117fc8ca973d0f3a2269Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-31c044afec62150ed234Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-6f006f7dd8fb4313bb4dSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-0900000000-9ab358a8bea057c26f2aSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-0900000000-45b4da314919775f4d8bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b733d425aecee271615fSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-6d8b96a01aee3a46f311Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-c0b68f0a70caf30dde61Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-372d6bf8c22bd7aeb50aSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-fef4343d64994e5383dcSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-3da25e2416a223eb8529Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fft-7930000000-7407d8205c3ca4de8df8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054k-9510000000-55fdc29c7e5ebc6c1393Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9500000000-fab7d8fe424250861d0bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1960000000-1dc3d4bd92c27f7b5848Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2910000000-9db8c31b2df0f599540dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9200000000-1386bb26d28d0f9dfa6eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ba-7950000000-683d6727b83458b9961fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-21f6ab78dfd677e72a53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-61a6cd864c33f5fb06b8Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID13632905
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDMOMORDIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).