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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:50:46 UTC

Update Date

2023-02-21 17:17:56 UTC

HMDB ID

HMDB0013195

Secondary Accession Numbers

HMDB13195

Metabolite Identification

Common Name

4-Aminobiphenyl

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.667  10.780   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    8   11                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   12                                                       
CONECT   10    4    5   11                                                  
CONECT   11    6    7   10                                                  
CONECT   12    8    9   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-1,1'-biphenyl	ChEBI
4-Aminodiphenyl	ChEBI
4-Biphenylamine	ChEBI
Biphenyl-4-ylamine	ChEBI
p-Aminodiphenyl	ChEBI
p-Biphenylamine	ChEBI
p-Phenylaniline	ChEBI
p-Xenylamine	ChEBI
Paraaminodiphenyl	ChEBI
(1,1'-Biphenyl)-4-amine	HMDB
(4-Phenyl-phenyl)-amine	HMDB
4-Aminobifenyl	HMDB
4-Aminodifenil	HMDB
4-Bifenylamin	HMDB
4-Biphenylamine hydrochloride	HMDB, MeSH
4-Biphenylylamine	HMDB
4-Phenylaniline	HMDB
Aminobiphenyl	HMDB
Biphenyl-4-amine	HMDB
Biphenylamine	HMDB
P-Aminobiphenyl	HMDB
Xenylamin	HMDB
Xenylamine	HMDB
[1,1'-Biphenyl]-4-amine	HMDB
[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 ion	MeSH, HMDB
4-Aminobiphenyl	ChEBI

Chemical Formula

C₁₂H₁₁N

Average Molecular Weight

169.2224

Monoisotopic Molecular Weight

169.089149357

IUPAC Name

[1,1'-biphenyl]-4-amine

Traditional Name

4-aminobiphenyl

CAS Registry Number

92-67-1

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 Key

DMVOXQPQNTYEKQ-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobiphenyl (CHEBI:1784 )

Ontology

Physiological effect

Health effect

Cancer

Cancer (HMDB: HMDB0013195)

Observation

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0013195)
Cell membrane (HMDB: HMDB0013195)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0013195)
Inhalation (HMDB: HMDB0013195)

Enteral

Ingestion (HMDB: HMDB0013195)

Source

Endogenous

Endogenous (HMDB: HMDB0013195)

Exogenous

Synthetic

Synthetic (HMDB: HMDB0013195)

Environmental

Tobacco Smoke (HMDB: HMDB0013195)

Process

Not Available

Role

Indirect biological role

Carcinogen (HMDB: HMDB0013195)

Environmental role

Air pollutant (HMDB: HMDB0013195)

Biological role

Carcinogenic agent (HMDB: HMDB0013195)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	53.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.86	MARTIN-VILLODRE,A ET AL. (1986)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.79	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	4.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	55.89 m³·mol⁻¹	ChemAxon
Polarizability	19.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.894	31661259
DarkChem	[M-H]-	136.466	31661259
DeepCCS	[M+H]+	138.862	30932474
DeepCCS	[M-H]-	136.309	30932474
DeepCCS	[M-2H]-	172.013	30932474
DeepCCS	[M+Na]+	147.091	30932474
AllCCS	[M+H]+	136.6	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	141.0	32859911
AllCCS	[M+Na]+	142.2	32859911
AllCCS	[M-H]-	138.4	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	139.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.1 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9623 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.92 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2015.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	494.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	319.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	400.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	487.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	215.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1355.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	423.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	895.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	465.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	197.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	33.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Aminobiphenyl	NC1=CC=C(C=C1)C1=CC=CC=C1	2623.8	Standard polar	33892256
4-Aminobiphenyl	NC1=CC=C(C=C1)C1=CC=CC=C1	1692.3	Standard non polar	33892256
4-Aminobiphenyl	NC1=CC=C(C=C1)C1=CC=CC=C1	1755.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	1991.1	Semi standard non polar	33892256
4-Aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	2043.0	Standard non polar	33892256
4-Aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	2226.4	Standard polar	33892256
4-Aminobiphenyl,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C	2016.3	Semi standard non polar	33892256
4-Aminobiphenyl,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C	2096.0	Standard non polar	33892256
4-Aminobiphenyl,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C	2198.8	Standard polar	33892256
4-Aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	2241.0	Semi standard non polar	33892256
4-Aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	2253.7	Standard non polar	33892256
4-Aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=CC=C2)C=C1	2377.0	Standard polar	33892256
4-Aminobiphenyl,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2473.8	Semi standard non polar	33892256
4-Aminobiphenyl,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2514.9	Standard non polar	33892256
4-Aminobiphenyl,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2396.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Aminobiphenyl EI-B (Non-derivatized)	splash10-014i-6900000000-485d158d46307e7e68a3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Aminobiphenyl EI-B (Non-derivatized)	splash10-014i-6900000000-485d158d46307e7e68a3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1900000000-7cc97adc9c729451bd04	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-5900000000-2d12ae7fb469d0456cac	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Positive-QTOF	splash10-00di-0900000000-ea4ddfd09aa02c5ce68d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Positive-QTOF	splash10-00di-0900000000-bf153c3905690bdc5b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Positive-QTOF	splash10-00kf-3900000000-2b96b507b444a3cfbeff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Negative-QTOF	splash10-014i-0900000000-8b7346091e37cac9abd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Negative-QTOF	splash10-014i-0900000000-8b7346091e37cac9abd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Negative-QTOF	splash10-014i-2900000000-c5ddef1d7d563f1bb3d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Positive-QTOF	splash10-00di-0900000000-f04809ed8d3ffdb9e395	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Positive-QTOF	splash10-00di-0900000000-f04809ed8d3ffdb9e395	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Positive-QTOF	splash10-014l-0900000000-b4d0aef74055dd87486f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 10V, Negative-QTOF	splash10-014i-0900000000-c8884063706b25aca801	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 20V, Negative-QTOF	splash10-014i-0900000000-c8884063706b25aca801	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminobiphenyl 40V, Negative-QTOF	splash10-014i-0900000000-0e190a36e93b266cb602	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029326

KNApSAcK ID

Not Available

Chemspider ID

6835

KEGG Compound ID

C10998

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Aminobiphenyl

METLIN ID

Not Available

PubChem Compound

7102

PDB ID

Not Available

ChEBI ID

1784

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1372051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 4-Aminobiphenyl (HMDB0013195)

MOL for HMDB0013195 (4-Aminobiphenyl)

3D MOL for HMDB0013195 (4-Aminobiphenyl)

3D SDF for HMDB0013195 (4-Aminobiphenyl)

3D-SDF for HMDB0013195 (4-Aminobiphenyl)

PDB for HMDB0013195 (4-Aminobiphenyl)

3D PDB for HMDB0013195 (4-Aminobiphenyl)

SMILES for HMDB0013195 (4-Aminobiphenyl)

INCHI for HMDB0013195 (4-Aminobiphenyl)

Structure for HMDB0013195 (4-Aminobiphenyl)

3D Structure for HMDB0013195 (4-Aminobiphenyl)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra