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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:03:25 UTC
HMDB IDHMDB0001169
Secondary Accession Numbers
  • HMDB01169
Metabolite Identification
Common Name4-Aminophenol
Description4-aminophenol is considered a minor nephrotoxic metabolite of phenacetin and acetaminophen (paracetamol) in man. 4-Aminophenol can undergo autoxidations and metal-catalyzed and enzymatic oxidations in man to produce reactive oxygen species. (PMID 1713494 ).
Structure
Thumb
Synonyms
ValueSource
4-AminobenzenolChEBI
4-HydroxyanilineChEBI
P-AminophenolChEBI
P-HydroxyanilineChEBI
1-amino-4-HydroxybenzeneHMDB
4-amino-1-HydroxybenzeneHMDB
ActivolHMDB
AminophenolHMDB
EnergolHMDB
Fouramine PHMDB
P-HydroxyphenylamineHMDB
ParamidophenolHMDB
ParanolHMDB
4-Aminophenol hydrochlorideMeSH
P-Aminophenol phosphateMeSH
4-Aminophenol monosodium saltMeSH
4-Aminophenol, 3H-labeledMeSH
4-Aminophenol, ion(1+)MeSH
4-Aminophenol conjugate monoacidMeSH
4-Aminophenol monopotassium saltMeSH
4-Aminophenol, 18O-labeledMeSH
Para-aminophenolMeSH
4-Aminophenol sulfateMeSH
4-Aminophenol sulfate (2:1)MeSH
Chemical FormulaC6H7NO
Average Molecular Weight109.1259
Monoisotopic Molecular Weight109.052763851
IUPAC Name4-aminophenol
Traditional Nameaminophenol
CAS Registry Number123-30-8
SMILES
NC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
InChI KeyPLIKAWJENQZMHA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • P-aminophenol
  • Aniline or substituted anilines
  • Aminophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Tissue and substructures:

  Organ and components:

Source:

Route of exposure:

  Parenteral:

  Enteral:

Physiological effect

Health effect:

  Observation:

  Health condition:

    General disorders and administration site conditions:

    Nervous system disorders:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Indirect biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point187.5 °CNot Available
Water Solubility16 mg/mLNot Available
LogP0.04HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility121 g/LALOGPS
logP0.47ALOGPS
logP0.84ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)10.4ChemAxon
pKa (Strongest Basic)5.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability11.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-9c5bfea7a6ff3c845001View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pe9-9300000000-8ff47e2157f6fbfe6754View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-1890000000-c8247060f46131c693d1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1927000000-b873199d9ac85605a4dfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-e64da39e73e3c0ea696cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-060r-6900000000-2c6cd652b49e26ce3fceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-3900000000-906f96b14dfdad2310deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-d56be0077647bc66e962View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-937794addf5b73c988e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-2900000000-1d20b6ad92e8fe4dcb55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-da3b2114d9298a0363e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-b43943b1e137b2912b0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9000000000-8ca8655366b90d8f42dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-28f35dbe83fee57d4a70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-6aa4cd1a9d2a859fa70bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-9300000000-177dcaf10b9e95cb409cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9700000000-00bffb48fd955696bcccView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Epidermis
  • Spleen
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.00 (0.03-20.00) uMAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022462
KNApSAcK IDNot Available
Chemspider ID392
KEGG Compound IDC02372
BioCyc IDCPD-259
BiGG IDNot Available
Wikipedia LinkAminophenol
METLIN ID6051
PubChem Compound403
PDB ID4NL
ChEBI ID17602
References
Synthesis ReferenceZhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lampinen M, Bondesson U, Fredriksson E, Hedeland M: Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):347-54. [PubMed:12742125 ]
  2. Clark PM, Clark JD, Wheatley T: Urine discoloration after acetaminophen overdose. Clin Chem. 1986 Sep;32(9):1777-8. [PubMed:3742803 ]
  3. Kanishchev PA, Bereza NM, Seniuk VF, Perevziaka AV: [Quantitative determination of blood loss from the gastrointestinal tract using Metol in chronic diseases of the digestive organs]. Lab Delo. 1989;(3):36-8. [PubMed:2469837 ]
  4. Xu Y, Halsall B, Heineman WR: Heterogeneous enzyme immunoassay of alpha-fetoprotein in maternal serum by flow-injection amperometric detection of 4-aminophenol. Clin Chem. 1990 Nov;36(11):1941-4. [PubMed:1700742 ]
  5. Bomhard EM, Herbold BA: Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol. 2005 Dec;35(10):783-835. [PubMed:16468500 ]
  6. Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, Leclaire J: Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett. 2005 Sep 15;158(3):196-212. [PubMed:15890478 ]
  7. Van Bocxlaer JF, Clauwaert KM, Lambert WE, De Leenheer AP: Quantitative colorimetric determination of urinary p-aminophenol with an automated analyzer. Clin Chem. 1997 Apr;43(4):627-34. [PubMed:9105264 ]
  8. Gil EP, Tang HT, Halsall HB, Heineman WR, Misiego AS: Competitive heterogeneous enzyme immunoassay for theophylline by flow-injection analysis with electrochemical detection of p-aminophenol. Clin Chem. 1990 Apr;36(4):662-5. [PubMed:2138937 ]
  9. Arndt CA, Colvin OM, Balis FM, Lester CM, Johnson G, Poplack DG: Intrathecal administration of 4-hydroperoxycyclophosphamide in rhesus monkeys. Cancer Res. 1987 Nov 15;47(22):5932-4. [PubMed:3664493 ]
  10. Hegedus ZL, Nayak U: Para-aminophenol and structurally related compounds as intermediates in lipofuscin formation and in renal and other tissue toxicities. Arch Int Physiol Biochim Biophys. 1991 Feb;99(1):99-105. [PubMed:1713494 ]