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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:50:46 UTC
Update Date2020-02-26 21:38:19 UTC
HMDB IDHMDB0013195
Secondary Accession Numbers
  • HMDB13195
Metabolite Identification
Common Name4-Aminobiphenyl
Description4-Aminobiphenyl, also known as 4-biphenylamine or p-phenylaniline, belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. 4-Aminobiphenyl is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Aminobiphenyl is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a small amount of articles have been published on 4-Aminobiphenyl.
Structure
Data?1582753099
Synonyms
ValueSource
4-Amino-1,1'-biphenylChEBI
4-AminodiphenylChEBI
4-BiphenylamineChEBI
Biphenyl-4-ylamineChEBI
p-AminodiphenylChEBI
p-BiphenylamineChEBI
p-PhenylanilineChEBI
p-XenylamineChEBI
ParaaminodiphenylChEBI
(1,1'-Biphenyl)-4-amineHMDB
(4-Phenyl-phenyl)-amineHMDB
4-AminobifenylHMDB
4-AminodifenilHMDB
4-BifenylaminHMDB
4-Biphenylamine hydrochlorideHMDB, MeSH
4-BiphenylylamineHMDB
4-PhenylanilineHMDB
AminobiphenylHMDB
Biphenyl-4-amineHMDB
BiphenylamineHMDB
P-AminobiphenylHMDB
XenylaminHMDB
XenylamineHMDB
[1,1'-Biphenyl]-4-amineHMDB
[1,1'-Biphenyl]-4-amine (acd/name 4.0)HMDB
[1,1'-Biphenyl]-4-ylamine (acd/name 4.0)HMDB
{[1,1'-biphenyl]-4-amine}HMDB
4-Biphenylnitrenium ionMeSH, HMDB
4-AminobiphenylChEBI
Chemical FormulaC12H11N
Average Molecular Weight169.2224
Monoisotopic Molecular Weight169.089149357
IUPAC Name[1,1'-biphenyl]-4-amine
Traditional Name4-aminobiphenyl
CAS Registry Number92-67-1
SMILES
NC1=CC=C(C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2
InChI KeyDMVOXQPQNTYEKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point53.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.86MARTIN-VILLODRE,A ET AL. (1986)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(2.89) g/LALOGPS
logP10(2.79) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Basic)4.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.89 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.89431661259
DarkChem[M-H]-136.46631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-AminobiphenylNC1=CC=C(C=C1)C1=CC=CC=C12623.8Standard polar33892256
4-AminobiphenylNC1=CC=C(C=C1)C1=CC=CC=C11692.3Standard non polar33892256
4-AminobiphenylNC1=CC=C(C=C1)C1=CC=CC=C11755.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Aminobiphenyl,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C11991.1Semi standard non polar33892256
4-Aminobiphenyl,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C12043.0Standard non polar33892256
4-Aminobiphenyl,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C12226.4Standard polar33892256
4-Aminobiphenyl,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C2016.3Semi standard non polar33892256
4-Aminobiphenyl,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C2096.0Standard non polar33892256
4-Aminobiphenyl,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C2198.8Standard polar33892256
4-Aminobiphenyl,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C12241.0Semi standard non polar33892256
4-Aminobiphenyl,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C12253.7Standard non polar33892256
4-Aminobiphenyl,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C12377.0Standard polar33892256
4-Aminobiphenyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C2473.8Semi standard non polar33892256
4-Aminobiphenyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C2514.9Standard non polar33892256
4-Aminobiphenyl,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C2396.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Aminobiphenyl EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminobiphenyl EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-7cc97adc9c729451bd042017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminobiphenyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-5900000000-2d12ae7fb469d0456cac2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Positive-QTOFsplash10-00di-0900000000-ea4ddfd09aa02c5ce68d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Positive-QTOFsplash10-00di-0900000000-bf153c3905690bdc5b592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Positive-QTOFsplash10-00kf-3900000000-2b96b507b444a3cfbeff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Negative-QTOFsplash10-014i-0900000000-8b7346091e37cac9abd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Negative-QTOFsplash10-014i-0900000000-8b7346091e37cac9abd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Negative-QTOFsplash10-014i-2900000000-c5ddef1d7d563f1bb3d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Positive-QTOFsplash10-00di-0900000000-f04809ed8d3ffdb9e3952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Positive-QTOFsplash10-00di-0900000000-f04809ed8d3ffdb9e3952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Positive-QTOFsplash10-014l-0900000000-b4d0aef74055dd87486f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Negative-QTOFsplash10-014i-0900000000-c8884063706b25aca8012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Negative-QTOFsplash10-014i-0900000000-c8884063706b25aca8012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Negative-QTOFsplash10-014i-0900000000-0e190a36e93b266cb6022021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029326
KNApSAcK IDNot Available
Chemspider ID6835
KEGG Compound IDC10998
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Aminobiphenyl
METLIN IDNot Available
PubChem Compound7102
PDB IDNot Available
ChEBI ID1784
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1372051
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakanishi H, Takeuchi S, Kato K, Shimizu S, Kobayashi K, Tatematsu M, Shirai T: Establishment and characterization of three androgen-independent, metastatic carcinoma cell lines from 3,2'-dimethyl-4-aminobiphenyl-induced prostatic tumors in F344 rats. Jpn J Cancer Res. 1996 Dec;87(12):1218-26. [PubMed:9045956 ]