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Identification
NameTrinitrotoluene
Accession NumberDB01676  (EXPT03079)
TypeSmall Molecule
GroupsExperimental
Description

A 2,4,6-trinitrotoluene is an explosive chemical that can cause skin irritation and other toxic consequences. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2,4,6-TNTNot AvailableNot Available
2,4,6-trinitrotolueneNot AvailableNot Available
2,4,6-TrinitrotoluolNot AvailableNot Available
TNTNot AvailableNot Available
α-TNTNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number118-96-7
WeightAverage: 227.1311
Monoisotopic: 227.017834907
Chemical FormulaC7H5N3O6
InChI KeySPSSULHKWOKEEL-UHFFFAOYSA-N
InChI
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
IUPAC Name
2-methyl-1,3,5-trinitrobenzene
SMILES
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes. These 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
  • Toluene
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9227
Blood Brain Barrier+0.8716
Caco-2 permeable+0.6001
P-glycoprotein substrateNon-substrate0.8312
P-glycoprotein inhibitor INon-inhibitor0.7654
P-glycoprotein inhibitor IINon-inhibitor0.9723
Renal organic cation transporterNon-inhibitor0.9101
CYP450 2C9 substrateNon-substrate0.7236
CYP450 2D6 substrateNon-substrate0.8382
CYP450 3A4 substrateNon-substrate0.5481
CYP450 1A2 substrateInhibitor0.9091
CYP450 2C9 substrateNon-inhibitor0.8706
CYP450 2D6 substrateNon-inhibitor0.9129
CYP450 2C19 substrateNon-inhibitor0.6601
CYP450 3A4 substrateNon-inhibitor0.9393
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7988
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.5607
BiodegradationNot ready biodegradable0.9095
Rat acute toxicity2.8029 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8347
hERG inhibition (predictor II)Non-inhibitor0.9412
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point80.1 °CPhysProp
water solubility115 mg/L (at 23 °C)PHELAN,JM & BARNETT,JL (2001)
logP1.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0778 mg/mLALOGPS
logP1.5ALOGPS
logP2.31ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area137.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.07 m3·mol-1ChemAxon
Polarizability17.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
References
Synthesis Reference

Hubert E. de Cazenove, Daniel Doyen, Jacques M. Dussidour, Jean-Jacques Gautier, “Process for continuous production of trinitrotoluene.” U.S. Patent US4022844, issued May, 1960.

US4022844
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (95.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pentaerythritol tetranitrate reductase

Kind: protein

Organism: Enterobacter cloacae

Pharmacological action: unknown

Components

Name UniProt ID Details
Pentaerythritol tetranitrate reductase P71278 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15