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2-Nitrophenol (T3D3579)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (10)XML
Targets (10)
Record Information
Version2.0
Creation Date2009-08-10 21:31:10 UTC
Update Date2014-12-24 20:26:10 UTC
Accession NumberT3D3579
Identification
Common Name2-Nitrophenol
ClassSmall Molecule
Description2-Nitrophenol is a phenolic compound that is used mainly to make dyes, paint coloring, rubber chemicals, and substances that kill molds. (5)
Compound Type
  • Aromatic Hydrocarbon
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
2-(hydroxy(oxido)amino)phenol
2-Hydroxynitrobenzene
2-nitrophenol ammonium salt
O-hydroxynitrobenzene
O-nitrofenol
O-nitrophenol
O-Nitrophenol
O-nitrophenol (molten)
Ortho-nitrophenol
Chemical FormulaC6H5NO3
Average Molecular Mass139.109 g/mol
Monoisotopic Mass139.027 g/mol
CAS Registry Number88-75-5
IUPAC Name2-nitrophenol
Traditional Nameo-nitrophenol
SMILESOC1=CC=CC=C1[N+]([O-])=O
InChI IdentifierInChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H
InChI KeyInChIKey=IQUPABOKLQSFBK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrophenols. Nitrophenols 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
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceLight yellow solid.
Experimental Properties
PropertyValue
Melting Point44.8°C
Boiling PointNot Available
Solubility2.5 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.25 g/LALOGPS
logP1.91ALOGPS
logP1.61ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.05 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.36 m³·mol⁻¹ChemAxon
Polarizability12.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9600000000-f334730ebce29cc98fdc2021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-c41839802d48c97c72b72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-465b86a7fa9c91aea0912021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0900000000-ceb07f366862a609f0862021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4r-0900000000-3d0f30b23eeba81f10482021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-052r-0900000000-1da0c5d7dfec9c4683402021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-052r-0900000000-d696815345f1828530d12021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0e903cf94b3c53ac4aa72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-4ba5e7ff168121879afd2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-4900000000-5a658d75ea75304f6bd62016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-00733f70f7b16c0d705d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-05d7e7d651eeffdea56b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-4900000000-412df114be028c848fda2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-9400000000-b9d470aedfc9324e848b2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-12View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5) ; eye contact (5).
Mechanism of ToxicityThe nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (1, 4)
MetabolismNitrophenol may be absorbed following ingestion, inhalation, or dermal exposure. The major metabolic route for nitrophenols is conjugation, with the resultant formation of either glucuronide or sulfate conjugates. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine. (5)
Toxicity ValuesLD50: 334 mg/kg (Oral, Rat) (3) LD50: 378 mg/kg (Intraperitoneal, Mouse) (3) LD50: 100 mg/kg (Intravenous, Dog) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources2-Nitrophenol is used mainly to make dyes, paint coloring, rubber chemicals, and substances that kill molds. (5)
Minimum Risk LevelNot Available
Health EffectsNitrophenols may cause methemoglobinemia. This is a disorder in which there is an abnormally high level of methemoglobin in the blood, resulting in a decrease in the amount of oxygen that can be carried to the tissues and organs. (5, 4)
SymptomsSymptoms of methemoglobinemia include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia may cause dysrhythmias, seizures, coma and death. (4)
TreatmentMethemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution at 1-2mg/kg administered intravenously slowly over five minutes followed by an IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6947
ChEMBL IDCHEMBL14205
ChemSpider ID13837787
KEGG IDC01988
UniProt IDNot Available
OMIM ID
ChEBI ID16260
BioCyc IDCPD-10489
CTD IDNot Available
Stitch ID2-Nitrophenol
PDB IDNot Available
ACToR ID1745
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3579.pdf
General References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Kuhn UD, Rost M, Muller D: Para-nitrophenol glucuronidation and sulfation in rat and human liver slices. Exp Toxicol Pathol. 2001 Apr;53(1):81-7. [11370739 ]
  3. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  4. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1992). Toxicological profile for nitrophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Hemoglobin subunit alpha
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
2. Hemoglobin subunit beta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
3. Hemoglobin subunit delta
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
4. Hemoglobin subunit epsilon
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
5. Hemoglobin subunit gamma-1
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
6. Hemoglobin subunit gamma-2
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
7. Hemoglobin subunit mu
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
8. Hemoglobin subunit theta-1
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
9. Hemoglobin subunit zeta
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Target Details
10. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.01 uMACEA_T47D_80hr_PositiveACEA Biosciences
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]