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Identification
Name2,4-Dinitrophenol
Accession NumberDB04528  (EXPT01235)
TypeSmall Molecule
GroupsExperimental
Description

A 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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentNitrophenols and Derivatives
Alternative parentsNitrobenzenes; Aminophenols; Nitronic Acids; Nitro Compounds; Organic Oxoazanium Compounds; Enols; Polyamines
Substituentsaminophenol; nitronic acid; nitro compound; polyamine; organic oxoazanium; enol; organonitrogen compound; amine
Classification descriptionThis compound belongs to the nitrophenols and derivatives. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both an hydroxyl group and a nitro group on two different ring carbon atoms.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9151
Blood Brain Barrier + 0.624
Caco-2 permeable - 0.5066
P-glycoprotein substrate Non-substrate 0.8481
P-glycoprotein inhibitor I Non-inhibitor 0.8236
P-glycoprotein inhibitor II Non-inhibitor 0.9634
Renal organic cation transporter Non-inhibitor 0.9235
CYP450 2C9 substrate Non-substrate 0.7366
CYP450 2D6 substrate Non-substrate 0.8541
CYP450 3A4 substrate Non-substrate 0.5572
CYP450 1A2 substrate Non-inhibitor 0.5154
CYP450 2C9 substrate Inhibitor 0.5678
CYP450 2D6 substrate Non-inhibitor 0.9346
CYP450 2C19 substrate Non-inhibitor 0.8584
CYP450 3A4 substrate Non-inhibitor 0.9304
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8322
Ames test Non AMES toxic 0.6697
Carcinogenicity Non-carcinogens 0.5981
Biodegradation Not ready biodegradable 0.8217
Rat acute toxicity 3.4118 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7701
hERG inhibition (predictor II) Non-inhibitor 0.9483
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 Solubility0.376ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra1D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC02496
PubChem Compound1493
PubChem Substance46507895
ChEBI918
ChEMBL
HETDNF
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pentaerythritol tetranitrate reductase

Kind: protein

Organism: Enterobacter cloacae

Pharmacological action: unknown

Components

Name UniProt ID Details
Pentaerythritol tetranitrate reductase P71278 Details
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:25