Human Metabolome Database Version 3.5

Showing metabocard for 4-Nitrophenol (HMDB01232)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:52 -0600
HMDB ID HMDB01232
Secondary Accession Numbers None
Metabolite Identification
Common Name 4-Nitrophenol
Description 4-Nitrophenol is a phenolic metabolite of environmental chemicals present in samples from the general population. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (PMID 15899376 Link_out) (Methods in Biotechnology, 2006,61-78).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Mononitrophenol
  2. p-Hydroxynitrobenzene
  3. 1-Hydroxy-4-nitrobenzene
  4. 4-Hydroxynitrobenzene
  5. 4-Nitrophenol
  6. Niphen
  7. p-Nitrophenol
  8. Paranitrophenol
Chemical Formula C6H5NO3
Average Molecular Weight 139.1088
Monoisotopic Molecular Weight 139.026943031
IUPAC Name 4-nitrophenol
Traditional IUPAC Name P-nitrophenol
CAS Registry Number 100-02-7
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 BTJIUGUIPKRLHP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Nitrophenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Nitrobenzenes
  • mononitrophenol(ChEBI)
Substituents
  • Aminophenol Derivative
  • Nitro Compound
  • Organic Oxoazanium
Direct Parent Nitrophenols and Derivatives
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 113.8 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 11.6 mg/mL Not Available
LogP 1.91 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 3.6 g/L ALOGPS
LogP 1.93 ALOGPS
LogP 1.61 ChemAxon
LogS -1.59 ALOGPS
pKa (strongest acidic) 7.04 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 66.05 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 35.36 ChemAxon
Polarizability 12.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (Unknown)
MS/MS Spectrum EI-B (HITACHI M-60)
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Placenta
  • Liver
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected but not Quantified
Not Applicable Not Available Not Available Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022503
KNApSAcK ID Not Available
Chemspider ID 955 Link_out
KEGG Compound ID C00870 Link_out
BioCyc ID P-NITROPHENOL Link_out
BiGG ID 36247 Link_out
Wikipedia Link 4-Nitrophenol Link_out
NuGOwiki Link HMDB01232 Link_out
Metagene Link HMDB01232 Link_out
METLIN ID 4100 Link_out
PubChem Compound 980 Link_out
PDB ID NPO Link_out
ChEBI ID 16836 Link_out
References
Synthesis Reference Fache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 (Tokyo). 1999 Aug;126(2):271-7. Pubmed: 10423517 Link_out
  2. 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. Pubmed: 15230116 Link_out
  3. 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. Pubmed: 1940590 Link_out
  4. 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. Pubmed: 8174252 Link_out
  5. 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. Pubmed: 8033255 Link_out
  6. 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. Pubmed: 7371150 Link_out
  7. 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. Pubmed: 8179202 Link_out
  8. 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. Pubmed: 16009282 Link_out
  9. 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. Pubmed: 8070326 Link_out
  10. 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. Pubmed: 12959278 Link_out
  11. 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. Pubmed: 9249878 Link_out
  12. 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. Pubmed: 6589361 Link_out
  13. Leng G, Lewalter J: Role of individual susceptibility in risk assessment of pesticides. Occup Environ Med. 1999 Jul;56(7):449-53. Pubmed: 10472315 Link_out
  14. 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. Pubmed: 9364930 Link_out
  15. 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. Pubmed: 12271274 Link_out
  16. 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. Pubmed: 15516026 Link_out
  17. 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. Pubmed: 6139755 Link_out
  18. 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. Pubmed: 15899376 Link_out

Enzymes
Name: Serum paraoxonase/lactonase 3
Reactions:
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenol details
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON3
Uniprot ID: Q15166 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline phosphatase, placental type
Reactions:
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric acid details
Gene Name: ALPP
Uniprot ID: P05187 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 1
Reactions:
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenol details
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON1
Uniprot ID: P27169 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 2
Reactions:
Parathion + Water unknown Diethylthiophosphate + 4-Nitrophenol details
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON2
Uniprot ID: Q15165 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Intestinal-type alkaline phosphatase
Reactions:
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric acid details
Gene Name: ALPI
Uniprot ID: P09923 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline phosphatase, tissue-nonspecific isozyme
Reactions:
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric acid details
Gene Name: ALPL
Uniprot ID: P05186 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tartrate-resistant acid phosphatase type 5
Reactions: Not Available
Gene Name: ACP5
Uniprot ID: P13686 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostatic acid phosphatase
Reactions: Not Available
Gene Name: ACPP
Uniprot ID: P15309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline phosphatase, placental-like
Reactions:
4-Nitrophenyl phosphate + Water unknown 4-Nitrophenol + Phosphoric acid details
Gene Name: ALPPL2
Uniprot ID: P10696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions:
4-Nitrophenol + NADPH + Oxygen unknown 4-Nitrocatechol + NADP + Water details
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid phosphatase type 6
Reactions: Not Available
Gene Name: ACP6
Uniprot ID: Q9NPH0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Testicular acid phosphatase
Reactions: Not Available
Gene Name: ACPT
Uniprot ID: Q9BZG2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein ACP1
Reactions: Not Available
Gene Name: ACP1
Uniprot ID: B5MCC7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA