Trinitrotoluene

Identification

Name
Trinitrotoluene
Accession Number
DB01676  (EXPT03079)
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
  • 2,4,6-TNT
  • 2,4,6-trinitrotoluene
  • 2,4,6-Trinitrotoluol
  • TNT
  • α-TNT
Categories
UNII
H43RF5TRM5
CAS number
118-96-7
Weight
Average: 227.1311
Monoisotopic: 227.017834907
Chemical Formula
C7H5N3O6
InChI Key
SPSSULHKWOKEEL-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPentaerythritol tetranitrate reductaseNot AvailableEnterobacter cloacae
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
KEGG Compound
C16391
PubChem Compound
8376
PubChem Substance
46507069
ChemSpider
8073
ChEBI
46053
ChEMBL
CHEMBL1236345
HET
TNL
Wikipedia
Trinitrotoluene
PDB Entries
1gvr / 4ab4 / 4aeo
MSDS
Download (95.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)80.1 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8706
CYP450 2D6 inhibitorNon-inhibitor0.9129
CYP450 2C19 inhibitorNon-inhibitor0.6601
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-03di-9460000000-f13fe3ac3044698c32a4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - APCI-ITFT , negativeLC-MS/MSsplash10-03di-0890000000-f022cff7bafbe3946255

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Nitrobenzenes
Direct Parent
Nitrobenzenes
Alternative Parents
Nitrotoluenes / Nitroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Nitrobenzene / Nitrotoluene / Nitroaromatic compound / 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
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
trinitrotoluene (CHEBI:46053) / an aromatic compound (CPD-9138)

Targets

Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Not Available
Gene Name
onr
Uniprot ID
P71278
Uniprot Name
Pentaerythritol tetranitrate reductase
Molecular Weight
39488.93 Da
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:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:47