Methyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate (T3D1076)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (5)XML
Targets (5)
Record Information
Version2.0
Creation Date2009-06-18 21:54:33 UTC
Update Date2014-12-24 20:23:06 UTC
Accession NumberT3D1076
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)
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Nitromethylene
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Methyl (3Z)-5-amino-3-(nitromethylene)-3H-1,2-dithiole-4-carboxylate
Chemical FormulaC6H6N2O4S2
Average Molecular Mass234.253 g/mol
Monoisotopic Mass233.977 g/mol
CAS Registry Number78649-93-1
IUPAC Namemethyl 5-amino-3-(nitromethylidene)-3H-1,2-dithiole-4-carboxylate
Traditional Namemethyl 3-amino-5-(nitromethylidene)-1,2-dithiole-4-carboxylate
SMILESCOC(=O)C1=C(N)SSC1=C[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 KeyInChIKey=IAWCIGLAQKOOTG-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
  • Methyl ester
  • 1,2-dithiole
  • Dithiole
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous amide
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • C-nitro compound
  • Organic disulfide
  • Organic nitro compound
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • 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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP0.28ALOGPS
logP0.42ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area98.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.63 m³·mol⁻¹ChemAxon
Polarizability20.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0290000000-5c5615890d1e429b865f2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-5920000000-9f3a8fe660c3b4fc61f62019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9100000000-c27c4a830c86e32897442019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0690000000-5abe13003b02d37c148a2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2930000000-dea1f7f36093a21e92752019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-2910000000-fccdf9d8c9ff31b005522019-02-23View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5479865
ChEMBL IDNot Available
ChemSpider ID4586506
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMethyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Acetylcholine receptor subunit beta
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB1
Uniprot ID:
P11230
Molecular Weight:
56697.9 Da
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Target Details
2. Neuronal acetylcholine receptor subunit alpha-3
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA3
Uniprot ID:
P32297
Molecular Weight:
57479.54 Da
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Target Details
3. Neuronal acetylcholine receptor subunit alpha-4
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
Molecular Weight:
69956.47 Da
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Target Details
4. Neuronal acetylcholine receptor subunit alpha-5
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA5
Uniprot ID:
P30532
Molecular Weight:
53053.965 Da
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Target Details
5. Neuronal acetylcholine receptor subunit beta-2
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
Gene Name:
CHRNB2
Uniprot ID:
P17787
Molecular Weight:
57018.575 Da
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.