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Showing NP-Card for 2,4,6-trinitrotoluene (NP0334596)

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Record Information
Version2.0
Created at2024-09-10 19:04:23 UTC
Updated at2024-09-10 19:04:23 UTC
NP-MRD IDNP0334596
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4,6-trinitrotoluene
Description 2,4,6-trinitrotoluene was first documented in 2009 (PMID: 19427119).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334596 (2,4,6-trinitrotoluene)

TNL
  Mrv0541 02231215382D          

 16 16  0  0  0  0            999 V2000
    0.4705    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2440   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6729   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.5143    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    1.9268    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
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3D MOL for NP0334596 (2,4,6-trinitrotoluene)

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3D SDF for NP0334596 (2,4,6-trinitrotoluene)
TNL
  Mrv0541 02231215382D          

 16 16  0  0  0  0            999 V2000
    0.4705    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1850   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1850   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8994   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2440   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584   -0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.9607    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6729   -1.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3874   -0.5482    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.9584    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.5143    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    1.9268    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  6   4   1   6  -1   9   1  11  -1  14   1  16  -1
M  END
> <DATABASE_ID>
NP0334596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3

> <INCHI_KEY>
SPSSULHKWOKEEL-UHFFFAOYSA-N

> <FORMULA>
C7H5N3O6

> <MOLECULAR_WEIGHT>
227.1311

> <EXACT_MASS>
227.017834907

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
17.897497947806563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-1,3,5-trinitrobenzene

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
2.306619773333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.99115470103241

> <JCHEM_POLAR_SURFACE_AREA>
137.45999999999998

> <JCHEM_REFRACTIVITY>
53.07330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-tnt

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334596 (2,4,6-trinitrotoluene)
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PDB for NP0334596 (2,4,6-trinitrotoluene)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: TNL                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.878   0.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.212   1.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.878  -1.023   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.212  -1.793   0.000  0.00  0.00           N+1
HETATM    5  O   UNK     0       2.212  -3.333   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.546  -1.023   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0      -0.455  -1.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.789  -1.023   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.123  -1.793   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0      -3.123  -3.333   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.456  -1.023   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      -1.789   0.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.455   1.287   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.455   2.827   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0      -1.789   3.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.878   3.597   0.000  0.00  0.00           O-1
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13    1   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0334596 (2,4,6-trinitrotoluene)
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SMILES for NP0334596 (2,4,6-trinitrotoluene)
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
Download
INCHI for NP0334596 (2,4,6-trinitrotoluene)
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
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View in JSmol
Synonyms
ValueSource
1-Methyl-2,4,6-trinitrobenzeneChEBI
2,4,6-TNTChEBI
2,4,6-TrinitrotoluolChEBI
alpha-TNTChEBI
S-TrinitrotolueneChEBI
S-TrinitrotoluolChEBI
Sym-trinitrotoluolChEBI
TNTChEBI
TrinitrotoluenChEBI
TrinitrotoluolChEBI
TritolChEBI
TrotylChEBI
2,4,6-TrinitrotolueneKegg
a-TNTGenerator
Α-TNTGenerator
TrinitrotolueneChEBI
Chemical FormulaC7H5N3O6
Average Mass227.1311 Da
Monoisotopic Mass227.01783 Da
IUPAC Name2-methyl-1,3,5-trinitrobenzene
Traditional Nameα-tnt
CAS Registry NumberNot Available
SMILES
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI Identifier
InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
InChI KeySPSSULHKWOKEEL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • 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
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.5ALOGPS
logP2.31ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area137.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.07 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB01676  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030299  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16391  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrinitrotoluene  
METLIN IDNot Available
PubChem Compound8376  
PDB IDNot Available
ChEBI ID46053  
Good Scents IDNot Available
References
General References
  1. Chen WS, Huang GC: Sonochemical decomposition of dinitrotoluenes and trinitrotoluene in wastewater. J Hazard Mater. 2009 Sep 30;169(1-3):868-74. doi: 10.1016/j.jhazmat.2009.04.028.  Epub 2009 Apr 15. [PubMed:19427119  ] 
  2. Lotufo GR, Blackburn WM, Gibson AB: Toxicity of trinitrotoluene to sheepshead minnows in water exposures. Ecotoxicol Environ Saf. 2010 Jul;73(5):718-26. doi: 10.1016/j.ecoenv.2010.02.007.  Epub 2010 Mar 9. [PubMed:20219247  ] 
  3. Okochi M, Muto M, Yanai K, Tanaka M, Onodera T, Wang J, Ueda H, Toko K: Array-Based Rational Design of Short Peptide Probe-Derived from an Anti-TNT Monoclonal Antibody. ACS Comb Sci. 2017 Oct 9;19(10):625-632. doi: 10.1021/acscombsci.7b00035. Epub  2017 Sep 8. [PubMed:28845964  ]