You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name2,4-Dinitrophenol
Accession NumberDB04528  (EXPT01235)
TypeSmall Molecule
GroupsExperimental
DescriptionA toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed)
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQ13SKS21MN
CAS number51-28-5
WeightAverage: 184.1064
Monoisotopic: 184.012021248
Chemical FormulaC6H4N2O5
InChI KeyUFBJCMHMOXMLKC-UHFFFAOYSA-N
InChI
InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H
IUPAC Name
2,4-dinitrophenol
SMILES
OC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Pentaerythritol tetranitrate reductaseProteinunknownNot AvailableEnterobacter cloacaeP71278 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

Otto Arndt, Theodor Papenfuhs, “Process for the preparation of 6-chloro-2,4-dinitrophenol.” U.S. Patent US4540832, issued September, 1984.

US4540832
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9151
Blood Brain Barrier+0.624
Caco-2 permeable-0.5066
P-glycoprotein substrateNon-substrate0.8481
P-glycoprotein inhibitor INon-inhibitor0.8236
P-glycoprotein inhibitor IINon-inhibitor0.9634
Renal organic cation transporterNon-inhibitor0.9235
CYP450 2C9 substrateNon-substrate0.7366
CYP450 2D6 substrateNon-substrate0.8541
CYP450 3A4 substrateNon-substrate0.5572
CYP450 1A2 substrateNon-inhibitor0.5154
CYP450 2C9 inhibitorInhibitor0.5678
CYP450 2D6 inhibitorNon-inhibitor0.9346
CYP450 2C19 inhibitorNon-inhibitor0.8584
CYP450 3A4 inhibitorNon-inhibitor0.9304
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8322
Ames testNon AMES toxic0.6697
CarcinogenicityNon-carcinogens0.5981
BiodegradationNot ready biodegradable0.8217
Rat acute toxicity3.4118 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7701
hERG inhibition (predictor II)Non-inhibitor0.9483
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point115.5 °CPhysProp
water solubility2790 mg/L (at 20 °C)SCHWARZENBACH,RP ET AL (1988)
logP1.67HANSCH,C ET AL. (1995)
pKa4.09 (at 25 °C)PEARCE,PJ & SIMKINS,RJJ (1968)
Predicted Properties
PropertyValueSource
Water Solubility0.376 mg/mLALOGPS
logP1.89ALOGPS
logP1.55ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.87 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.69 m3·mol-1ChemAxon
Polarizability14.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0gx0-9400000000-1a15393a48ca40633fc2View in MoNA
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitrophenols and derivatives. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentNitrophenols and derivatives
Alternative Parents
Substituents
  • Nitrophenol derivative
  • Nitrobenzene
  • 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
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
unknown
General Function:
Oxidoreductase activity
Specific Function:
Not Available
Gene Name:
onr
Uniprot ID:
P71278
Molecular Weight:
39488.93 Da
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24