2,4-Dinitrophenol

Identification

Name
2,4-Dinitrophenol
Accession Number
DB04528  (EXPT01235)
Type
Small Molecule
Groups
Experimental
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
Synonyms
  • Dinitrophenol
External IDs
NSC-1532
Categories
UNII
Q13SKS21MN
CAS number
51-28-5
Weight
Average: 184.1064
Monoisotopic: 184.012021248
Chemical Formula
C6H4N2O5
InChI Key
UFBJCMHMOXMLKC-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPentaerythritol tetranitrate reductaseNot AvailableEnterobacter 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
KEGG Compound
C02496
PubChem Compound
1493
PubChem Substance
46507895
ChemSpider
1448
ChEBI
42017
ChEMBL
CHEMBL273386
HET
DNF
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
1gvo / 1oau / 2b14 / 2b15 / 2b16 / 3air / 3aiw / 3vo0
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0w33-9300000000-b1719d21caddddc047cb
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0900000000-5413dbaa2e83c8f4b557
GC-MS Spectrum - EI-BGC-MSsplash10-0gz9-9200000000-e0169c5ed661f777992d
Mass Spectrum (Electron Ionization)MSsplash10-0gx0-9400000000-1a15393a48ca40633fc2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-d0edc53122fee24d0bfe
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0900000000-c84e9386e3bb5b82491b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0abi-1900000000-68bdd4eb6e5974914142
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-3900000000-e783e75f0ce9280a1b98
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4j-9700000000-57819c29c3eccdb05da8
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-3a8e56d08e6de49313c9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-1aa1a96cd6fcabd2e8b2
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Nitrophenols
Direct Parent
Dinitrophenols
Alternative Parents
Nitrobenzenes / Nitroaromatic compounds / 1-hydroxy-2-unsubstituted benzenoids / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Dinitrophenol / Nitrobenzene / Nitroaromatic compound / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / C-nitro compound / Organic nitro compound / Organic oxoazanium / Allyl-type 1,3-dipolar organic compound / Propargyl-type 1,3-dipolar organic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dinitrophenol (CHEBI:42017)

Targets

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

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:35