Methyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate (CHEM000926)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-06-18 21:54:33 UTC
Update Date2026-04-05 15:27:15 UTC
Accession NumberCHEM000926
Identification
Common NameMethyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate
ClassSmall Molecule
DescriptionAromatic heterocycle containing a nitromethylene substituent. Fast acting neurotoxicant, effective both by contact or oral ingestion; they are relatively safe to vertebrates and degrade rapidly in the environment. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Nitromethylene
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Methyl (3Z)-5-amino-3-(nitromethylene)-3H-1,2-dithiole-4-carboxylic acidGenerator
Methyl (3Z)-5-amino-3-(nitromethylidene)-3H-1,2-dithiole-4-carboxylic acidGenerator
Chemical FormulaC6H6N2O4S2
Average Molecular Mass234.240 g/mol
Monoisotopic Mass233.977 g/mol
CAS Registry Number78649-93-1
IUPAC Namemethyl (3Z)-5-amino-3-(nitromethylidene)-3H-1,2-dithiole-4-carboxylate
Traditional Namemethyl (5Z)-3-amino-5-(nitromethylidene)-1,2-dithiole-4-carboxylate
SMILES[H]\C(=C1\SSC(N)=C1C(=O)OC)N(=O)=O
InChI IdentifierInChI=1S/C6H6N2O4S2/c1-12-6(9)4-3(2-8(10)11)13-14-5(4)7/h2H,7H2,1H3/b3-2-
InChI KeyIAWCIGLAQKOOTG-IHWYPQMZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vinylogous amides. These are organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassVinylogous amides
Sub ClassNot Available
Direct ParentVinylogous amides
Alternative Parents
Substituents
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Dithiole
  • 1,2-dithiole
  • Methyl ester
  • Organic nitro compound
  • Organic disulfide
  • C-nitro compound
  • Ketene acetal or derivatives
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP0.28ALOGPS
logP0.42ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)18.02ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area98.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.63 m³·mol⁻¹ChemAxon
Polarizability20.11 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-2190000000-273394ea9b4f62284b39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1190000000-a89a94e7b43640f00218Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-4761d0fb2584dfbdfd7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0290000000-f33de2c32f50033c7610Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9710000000-10e9c8a060f90ebaee34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9300000000-38aab9986fd47dc749e7Spectrum
Toxicity Profile
Route of ExposureDermal (1); Oral (1).
Mechanism of Toxicity Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNitromethylenes are used as pesticides. (1)
Minimum Risk LevelNot Available
Health EffectsNitromethylenes are neurotoxic. (1)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5479865
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available