Trinitrotoluene
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Identification
- Generic Name
- Trinitrotoluene
- DrugBank Accession Number
- DB01676
- Background
Trinitrotoluene is an explosive chemical that can cause skin irritation and other toxic consequences.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 227.1311
Monoisotopic: 227.017834907 - Chemical Formula
- C7H5N3O6
- Synonyms
- 2,4,6-TNT
- 2,4,6-trinitrotoluene
- 2,4,6-trinitrotoluol
- TNT
- α-TNT
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPentaerythritol tetranitrate reductase Not Available Enterobacter 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / C-nitro compound / Hydrocarbon derivative / Nitroaromatic compound / Nitrobenzene / Nitrotoluene / Organic 1,3-dipolar compound / Organic nitro compound / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- trinitrotoluene (CHEBI:46053) / an aromatic compound (CPD-9138)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H43RF5TRM5
- CAS number
- 118-96-7
- 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
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
- ZINC
- ZINC000014880028
- PDBe Ligand
- TNL
- Wikipedia
- Trinitrotoluene
- PDB Entries
- 1gvr / 4ab4 / 4aeo
- MSDS
- Download (95.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 80.1 °C PhysProp water solubility 115 mg/L (at 23 °C) PHELAN,JM & BARNETT,JL (2001) logP 1.60 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0778 mg/mL ALOGPS logP 1.5 ALOGPS logP 2.31 Chemaxon logS -3.5 ALOGPS Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 129.42 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 50.06 m3·mol-1 Chemaxon Polarizability 18.05 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9227 Blood Brain Barrier + 0.8716 Caco-2 permeable + 0.6001 P-glycoprotein substrate Non-substrate 0.8312 P-glycoprotein inhibitor I Non-inhibitor 0.7654 P-glycoprotein inhibitor II Non-inhibitor 0.9723 Renal organic cation transporter Non-inhibitor 0.9101 CYP450 2C9 substrate Non-substrate 0.7236 CYP450 2D6 substrate Non-substrate 0.8382 CYP450 3A4 substrate Non-substrate 0.5481 CYP450 1A2 substrate Inhibitor 0.9091 CYP450 2C9 inhibitor Non-inhibitor 0.8706 CYP450 2D6 inhibitor Non-inhibitor 0.9129 CYP450 2C19 inhibitor Non-inhibitor 0.6601 CYP450 3A4 inhibitor Non-inhibitor 0.9393 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7988 Ames test AMES toxic 0.9107 Carcinogenicity Carcinogens 0.5607 Biodegradation Not ready biodegradable 0.9095 Rat acute toxicity 2.8029 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8347 hERG inhibition (predictor II) Non-inhibitor 0.9412
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-03di-9460000000-f13fe3ac3044698c32a4 MS/MS Spectrum - APCI-ITFT , negative LC-MS/MS splash10-03di-0890000000-f022cff7bafbe3946255 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.9008237 predictedDarkChem Lite v0.1.0 [M-H]- 126.8168 predictedDeepCCS 1.0 (2019) [M+H]+ 154.7694237 predictedDarkChem Lite v0.1.0 [M+H]+ 130.08502 predictedDeepCCS 1.0 (2019) [M+Na]+ 137.68779 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPentaerythritol tetranitrate reductase
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51