T3DB: 4-Nitrophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (12)XML

Targets (12)

Record Information

Version

2.0

Creation Date

2009-03-06 18:58:23 UTC

Update Date

2014-12-24 20:21:25 UTC

Accession Number

T3D0257

Identification

Common Name

4-Nitrophenol

Class

Small Molecule

Description

4-Nitrophenol is a phenolic compound that is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (3) (Methods in Biotechnology, 2006,61-78) (23, 24)

Compound Type

Aromatic Hydrocarbon
Food Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Metabolite
Nitrite
Organic Compound
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-Hydroxy-4-nitrobenzene
4-Hydroxynitrobenzene
Mononitrophenol
Niphen
p-Hydroxynitrobenzene
p-Nitrophenol
para-Hydroxynitrobenzene
para-Nitrophenol
Paranitrophenol

Chemical Formula

C₆H₅NO₃

Average Molecular Mass

139.109 g/mol

Monoisotopic Mass

139.027 g/mol

CAS Registry Number

100-02-7

IUPAC Name

4-nitrophenol

Traditional Name

P-nitrophenol

SMILES

OC1=CC=C(C=C1)N(=O)=O

InChI Identifier

InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H

InChI Key

InChIKey=BTJIUGUIPKRLHP-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Nitrophenol
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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

mononitrophenol (CHEBI:16836 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Intestine
Liver
Placenta
Platelet

Pathways

Not Available

Applications

Not Available

Biological Roles

human xenobiotic metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless to light yellow solid.

Experimental Properties

Property	Value
Melting Point	113.8°C
Boiling Point	Not Available
Solubility	11.6 mg/mL at 20°C [SCHWARZENBACH,RP et al.(1988)]
LogP	1.91

Predicted Properties

Property	Value	Source
Water Solubility	3.6 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.61	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.36 m³·mol⁻¹	ChemAxon
Polarizability	12.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-670d24ff2b2b121a7ab8	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9400000000-b5aea5436a88b29179e9	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05n0-9300000000-f284a324180bf4d7ffc2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-2009127011-85632179856636169d28	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-1900000000-70af7d7902cd35a26f29	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kr-9200000000-6a367c2627bf30cad163	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00or-9500000000-a23a22fc322241325904	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-7900000000-d4915e2347113b56d32c	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9800000000-7bde61a3b7f0a23ddd41	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-00dl-0900000000-653240f82298b3880e70	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-014l-9100000000-1dd6a69ee33aeb4207a3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014r-9000000000-397a0913b382e58ae418	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kr-9200000000-039471e02c3307757a0c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-00or-9500000000-a23a22fc322241325904	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-000i-9400000000-12717928037244536b6b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-000i-9400000000-f133ed564f0a12bd3871	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-05n0-9300000000-d39a8dbf21962717a2ee	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9200000000-bff0a2a3c15629cc6ec2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-0900000000-1279a141e229fec8dbd4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0900000000-1279a141e229fec8dbd4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-9200000000-bff0a2a3c15629cc6ec2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00r6-9300000000-5cb2a9e8e318ca2474fd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-0c7b180f083127156f27	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-0900000000-c41839802d48c97c72b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-0900000000-465b86a7fa9c91aea091	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-052r-0900000000-7545ed558dcbc5a7a386	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-052r-0900000000-24c57afe8ccf403e589b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4r-2900000000-396ebc9986624989747e	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-d01a64d09fb568b883b1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-58e0d9a2ff9a60a8c4f6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-2900000000-fbf4f5da283a46ec8ed8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-3c17676b62ba6a9be8d5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-4dcec4bcef5be284e738	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-3900000000-de3f2773a5601a2eec1b	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kr-9300000000-d76f14df8da868057d44	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Toxicity Profile

Route of Exposure

Oral (23) ; inhalation (23) ; dermal (23)

Mechanism of Toxicity

The 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, 22)

Metabolism

Nitrophenol 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. (23)

Toxicity Values

LD50: 380 mg/kg (Oral, Mouse) (21) LD50: 75 mg/kg (Intraperitoneal, Mouse) (21)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

4-Nitrophenol is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. (23, 24)

Minimum Risk Level

Not Available

Health Effects

Nitrophenols 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. (23, 22)

Symptoms

Symptoms 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. (22)

Treatment

Methemoglobinemia 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. (22)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

168820

ChEBI ID

16836

BioCyc ID

P-NITROPHENOL

CTD ID

Not Available

Stitch ID

4-Nitrophenol

PDB ID

NPO

ACToR ID

1778

Wikipedia Link

4-Nitrophenol

References

Synthesis Reference

Not Available

MSDS

Link

General References

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 ]
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 ]
Bravo R, Caltabiano LM, Fernandez C, Smith KD, Gallegos M, Whitehead RD Jr, Weerasekera G, Restrepo P, Bishop AM, Perez JJ, Needham LL, Barr DB: Quantification of phenolic metabolites of environmental chemicals in human urine using gas chromatography-tandem mass spectrometry and isotope dilution quantification. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 25;820(2):229-36. Epub 2005 Apr 26. [15899376 ]
Ozawa S, Shimizu M, Katoh T, Miyajima A, Ohno Y, Matsumoto Y, Fukuoka M, Tang YM, Lang NP, Kadlubar FF: Sulfating-activity and stability of cDNA-expressed allozymes of human phenol sulfotransferase, ST1A3*1 ((213)Arg) and ST1A3*2 ((213)His), both of which exist in Japanese as well as Caucasians. J Biochem. 1999 Aug;126(2):271-7. [10423517 ]
Sharaev PN, Gabdrakhmanova NK, Strelkova TN, Sakhabutdinova EP: [Detection of N-acetyl-beta-D-hexosaminidase in urine]. Klin Lab Diagn. 2004 May;(5):40-2. [15230116 ]
Anderson RJ, Garcia MJ, Liebentritt DK, Kay HD: Localization of human blood phenol sulfotransferase activities: novel detection of the thermostable enzyme in granulocytes. J Lab Clin Med. 1991 Nov;118(5):500-9. [1940590 ]
Kayamori Y, Katayama Y: Enzymatic method for assaying calcium in serum and urine with porcine pancreatic alpha-amylase. Clin Chem. 1994 May;40(5):781-4. [8174252 ]
Pacifici GM, Temellini A, Castiglioni M, D'Alessandro C, Ducci A, Giuliani L: Interindividual variability of the human hepatic sulphotransferases. Chem Biol Interact. 1994 Jun;92(1-3):219-31. [8033255 ]
Bowers GN Jr, McComb RB, Christensen RG, Schaffer R: High-purity 4-nitrophenol: purification, characterization, and specifications for use as a spectrophotometric reference material. Clin Chem. 1980 May;26(6):724-9. [7371150 ]
Bellavite P, Andrioli G, Guzzo P, Arigliano P, Chirumbolo S, Manzato F, Santonastaso C: A colorimetric method for the measurement of platelet adhesion in microtiter plates. Anal Biochem. 1994 Feb 1;216(2):444-50. [8179202 ]
Pacifici GM: Sulfation of drugs and hormones in mid-gestation human fetus. Early Hum Dev. 2005 Jul;81(7):573-81. Epub 2004 Dec 8. [16009282 ]
Vitarius JA, Sultatos LG: Kinetic mechanism of the detoxification of the organophosphate paraoxon by human serum A-esterase. Drug Metab Dispos. 1994 May-Jun;22(3):472-8. [8070326 ]
Pacifici GM, Marchi G: Interindividual variability of phenol- and catechol-sulphotransferases in platelets from adults and newborns. Br J Clin Pharmacol. 1993 Dec;36(6):593-7. [12959278 ]
Osnes T, Sandstad O, Skar V, Osnes M: beta-Glucuronidase in common duct bile, methodological aspects, variation of pH optima and relation to gallstones. Scand J Clin Lab Invest. 1997 Jul;57(4):307-15. [9249878 ]
Young WF Jr, Okazaki H, Laws ER Jr, Weinshilboum RM: Human brain phenol sulfotransferase: biochemical properties and regional localization. J Neurochem. 1984 Sep;43(3):706-15. [6589361 ]
Leng G, Lewalter J: Role of individual susceptibility in risk assessment of pesticides. Occup Environ Med. 1999 Jul;56(7):449-53. [10472315 ]
Belanger G, Beaulieu M, Levesque E, Hum DW, Belanger A: Expression and characterization of a novel UDP-glucuronosyltransferase, UGT2B9, from cynomolgus monkey. DNA Cell Biol. 1997 Oct;16(10):1195-205. [9364930 ]
Birk AV, Broekman MJ, Gladek EM, Robertson HD, Drosopoulos JH, Marcus AJ, Szeto HH: Role of extracellular ATP metabolism in regulation of platelet reactivity. J Lab Clin Med. 2002 Sep;140(3):166-75. [12271274 ]
Rossi AM, Maggini V, Fredianelli E, Di Bello D, Pietrabissa A, Mosca F, Barale R, Pacifici GM: Phenotype-genotype relationships of SULT1A1 in human liver and variations in the IC50 of the SULT1A1 inhibitor quercetin. Int J Clin Pharmacol Ther. 2004 Oct;42(10):561-7. [15516026 ]
Reiter C, Mwaluko G, Dunnette J, Van Loon J, Weinshilboum R: Thermolabile and thermostable human platelet phenol sulfotransferase. Substrate specificity and physical separation. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):140-7. [6139755 ]
Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
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]
Wikipedia. 4-Nitrophenol. Last Updated 19 April 2009. [Link]

Gene Regulation

Up-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Down-Regulated Genes

Not Available

Targets

Target Details

1. Alpha-amylase 2B

General Function:: Not Available
Specific Function:: Alpha-amylase activity
Gene Name:: AMY2B
Uniprot ID:: P19961
Molecular Weight:: 57709.49 Da

References

Target Details

2. 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

Target Details

3. 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

Target Details

4. 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

Target Details

5. 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

Target Details

6. 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

Target Details

7. 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

Target Details

8. Hemoglobin subunit mu

General Function:: Oxygen transporter activity
Specific Function:: Not Available
Gene Name:: HBM
Uniprot ID:: Q6B0K9
Molecular Weight:: 15617.97 Da

References

Target Details

9. 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

Target Details

10. 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

Target Details

11. Sulfotransferase 1A1

General Function:: Sulfotransferase activity
Specific Function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:: SULT1A1
Uniprot ID:: P50225
Molecular Weight:: 34165.13 Da

References

Target Details

12. Androgen receptor

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Molecular Weight:: 98987.9 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.00 uM	Tox21_AR_BLA_Agonist_ratio	Tox21/NCGC
AC50	0.00 uM	Tox21_AR_LUC_MDAKB2_Agonist	Tox21/NCGC

References

4-Nitrophenol (T3D0257)

Structure for T3D0257: 4-Nitrophenol

Targets

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Binding/Activity Constants

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