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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:29 UTC
Update Date2019-07-23 06:11:15 UTC
HMDB IDHMDB0032558
Secondary Accession Numbers
  • HMDB32558
Metabolite Identification
Common NameDinitolmide
DescriptionDinitolmide, also known as D.O.T. or coccidine, belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups. Dinitolmide is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a broad-spectrum anticoccidial drug, preventing seven main strains of Eimeria coccidium. Dinitolmide is usually added to feed in doses of 125 ppm (preventive) or 250 ppm (curative). Dinitolmide (or zoalene) is a fodder additive for poultry, used to prevent coccidiosis infections. It leaves no residues in tissues. It is sold under trade names such as Coccidine A, Coccidot, and Zoamix. It can be also used to prevent coccidiosis of domestic rabbits.
Structure
Data?1563862275
Synonyms
ValueSource
D.O.T.Kegg
2-Methyl-3,5-dinitro-benzamideHMDB
2-Methyl-3,5-dinitrobenzamide, 9ciHMDB
3,5-Dinitro-O-toluamideHMDB
AbileneHMDB
CoccidineHMDB
Coccidine aHMDB
CoccidotHMDB
DinitolmidaHMDB
Dinitolmide, ban, innHMDB
DinitolmidumHMDB
DinitrotoluamideHMDB
MethyldinitrobenzamideHMDB
SalcostatHMDB
Whitsyn THMDB
ZamixHMDB
ZoaleneHMDB
ZoamixHMDB
Chemical FormulaC8H7N3O5
Average Molecular Weight225.1583
Monoisotopic Molecular Weight225.038570349
IUPAC Name2-methyl-3,5-dinitrobenzamide
Traditional Name2-methyl-3,5-dinitrobenzamide
CAS Registry Number148-01-6
SMILES
CC1=C(C=C(C=C1N(=O)=O)N(=O)=O)C(N)=O
InChI Identifier
InChI=1S/C8H7N3O5/c1-4-6(8(9)12)2-5(10(13)14)3-7(4)11(15)16/h2-3H,1H3,(H2,9,12)
InChI KeyZEFNOZRLAWVAQF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentDinitrotoluenes
Alternative Parents
Substituents
  • Dinitrotoluene
  • Benzamide
  • Benzoic acid or derivatives
  • Nitrobenzene
  • O-toluamide
  • Toluamide
  • Nitroaromatic compound
  • Benzoyl
  • Carboxamide group
  • C-nitro compound
  • Primary carboxylic acid amide
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic zwitterion
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP0.73ALOGPS
logP1.22ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.81ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area134.73 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.83 m³·mol⁻¹ChemAxon
Polarizability19.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9220000000-0ed4181a127531e0e7beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-5257a8757931e3fe876bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0190000000-144234dec36900b65206Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdk-1950000000-c7a5a0284bb9a1e66ad3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-9c1b6c5458e1f97509aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-ba1a5248693f0e490236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9130000000-978002d42f34ee95a2aeSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDDB11480
Phenol Explorer Compound IDNot Available
FooDB IDFDB010490
KNApSAcK IDNot Available
Chemspider ID2982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDinitolmide
METLIN IDNot Available
PubChem Compound3092
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .