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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:26 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060362
Secondary Accession Numbers
  • HMDB60362
Metabolite Identification
Common Name2,4-Diamino-6-nitrotoluene
Description2,4-Diamino-6-nitrotoluene, also known as 2-nitro-4,6-diaminotoluene, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2,4-Diamino-6-nitrotoluene is a strong basic compound (based on its pKa). 2,4-Diamino-6-nitrotoluene exists in all living organisms, ranging from bacteria to humans. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Structure
Data?1563866050
Synonyms
ValueSource
2-Nitro-4,6-diaminotolueneChEBI
Chemical FormulaC7H9N3O2
Average Molecular Weight167.1653
Monoisotopic Molecular Weight167.069476547
IUPAC Name4-methyl-5-nitrobenzene-1,3-diamine
Traditional Name2,4-diamino-6-nitrotoluene
CAS Registry NumberNot Available
SMILES
CC1=C(N)C=C(N)C=C1N(=O)=O
InChI Identifier
InChI=1S/C7H9N3O2/c1-4-6(9)2-5(8)3-7(4)10(11)12/h2-3H,8-9H2,1H3
InChI KeyDFZSBQYOXAUYCB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitrotoluene
  • Nitroaromatic compound
  • Aminotoluene
  • Aniline or substituted anilines
  • Toluene
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.46 g/LALOGPS
logP1.13ALOGPS
logP0.77ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)3.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.82 m³·mol⁻¹ChemAxon
Polarizability16.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.24231661259
DarkChem[M-H]-132.98631661259
DeepCCS[M+H]+136.40730932474
DeepCCS[M-H]-132.57930932474
DeepCCS[M-2H]-170.04830932474
DeepCCS[M+Na]+145.58730932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.432859911
AllCCS[M+NH4]+139.932859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-130.832859911
AllCCS[M+Na-2H]-131.932859911
AllCCS[M+HCOO]-133.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,4-Diamino-6-nitrotolueneCC1=C(N)C=C(N)C=C1N(=O)=O3025.7Standard polar33892256
2,4-Diamino-6-nitrotolueneCC1=C(N)C=C(N)C=C1N(=O)=O1857.9Standard non polar33892256
2,4-Diamino-6-nitrotolueneCC1=C(N)C=C(N)C=C1N(=O)=O1915.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,4-Diamino-6-nitrotoluene,1TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]1879.2Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]1976.2Standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]2338.6Standard polar33892256
2,4-Diamino-6-nitrotoluene,1TMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]1859.1Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]1975.8Standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2419.5Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]1993.2Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2075.0Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #1CC1=C(N[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2119.5Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]1949.1Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]2067.0Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N)C=C1[N+](=O)[O-]2264.0Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]1902.7Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2040.1Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2340.4Standard polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2016.0Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2129.6Standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N[Si](C)(C)C)C=C1[N+](=O)[O-]2077.4Standard polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #2CC1=C(N[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2015.7Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #2CC1=C(N[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2112.8Standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TMS,isomer #2CC1=C(N[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2087.3Standard polar33892256
2,4-Diamino-6-nitrotoluene,4TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2028.6Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,4TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]2224.4Standard non polar33892256
2,4-Diamino-6-nitrotoluene,4TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)C=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1[N+](=O)[O-]1997.4Standard polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2134.4Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2159.7Standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2446.1Standard polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2182.7Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2127.1Standard non polar33892256
2,4-Diamino-6-nitrotoluene,1TBDMS,isomer #2CC1=C(N)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2515.3Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2477.1Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2437.3Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2345.2Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2396.0Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2470.9Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N)C=C1[N+](=O)[O-]2407.4Standard polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2422.7Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2427.9Standard non polar33892256
2,4-Diamino-6-nitrotoluene,2TBDMS,isomer #3CC1=C(N)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2465.1Standard polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2690.7Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2742.1Standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2413.4Standard polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #2CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2681.9Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #2CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2736.6Standard non polar33892256
2,4-Diamino-6-nitrotoluene,3TBDMS,isomer #2CC1=C(N[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2419.3Standard polar33892256
2,4-Diamino-6-nitrotoluene,4TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2880.5Semi standard non polar33892256
2,4-Diamino-6-nitrotoluene,4TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2996.7Standard non polar33892256
2,4-Diamino-6-nitrotoluene,4TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1[N+](=O)[O-]2423.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diamino-6-nitrotoluene GC-MS (Non-derivatized) - 70eV, Positivesplash10-01b9-7900000000-6c2cfa70213df5608e382017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diamino-6-nitrotoluene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Diamino-6-nitrotoluene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 10V, Positive-QTOFsplash10-0uxr-0900000000-a592c7ee6768fc210bb52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 20V, Positive-QTOFsplash10-0udi-0900000000-2e14976aa7cd24a67f0b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 40V, Positive-QTOFsplash10-0uk9-1900000000-b352b16ef09ebd0fb9162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 10V, Negative-QTOFsplash10-014j-0900000000-06687ddbd81625493f6c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 20V, Negative-QTOFsplash10-014i-0900000000-913fe378446d8720e3302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Diamino-6-nitrotoluene 40V, Negative-QTOFsplash10-014j-1900000000-8ed928be717d71cd47952017-10-06Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16396
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound96177
PDB IDNot Available
ChEBI ID19342
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445
Reactions
2,4-Diamino-6-nitrotoluene + Acetyl-CoA → 4-Acetamido-2-amino-6-nitrotoluene + Coenzyme Adetails
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT2
Uniprot ID:
P11245
Molecular weight:
33570.245
Reactions
2,4-Diamino-6-nitrotoluene + Acetyl-CoA → 4-Acetamido-2-amino-6-nitrotoluene + Coenzyme Adetails