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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 05:53:00 UTC

Update Date

2023-02-21 17:31:06 UTC

HMDB ID

HMDB0062723

Secondary Accession Numbers

HMDB62723

Metabolite Identification

Common Name

N-hydroxy-4-aminobiphenyl

Description

N-hydroxy-4-aminobiphenyl, also known as 4-Biphenylhydroxylamine, is classified as a biphenyl or a Biphenyl derivative. Biphenyls are organic compounds containing to benzene rings linked together by a C-C bond. N-hydroxy-4-aminobiphenyl is considered to be practically insoluble (in water) and relatively neutral

Structure

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


  Mrv1652303231706522D          

 14 15  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062723

> <DATABASE_NAME>
hmdb

> <SMILES>
ONC1=CC=C(C=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO/c14-13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13-14H

> <INCHI_KEY>
MYVLYOJYVMLSFA-UHFFFAOYSA-N

> <FORMULA>
C12H11NO

> <MOLECULAR_WEIGHT>
185.226

> <EXACT_MASS>
185.084063978

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.57656958562781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{[1,1'-biphenyl]-4-yl}hydroxylamine

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.128741086666666

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.086506886337148

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.826041197909028

> <JCHEM_PKA_STRONGEST_BASIC>
5.051117020120735

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
58.18140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-hydroxy-4-aminobiphenyl

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Biphenylhydroxylamine	ChEBI
4-Hydroxyaminobiphenyl	ChEBI
4-Hydroxylaminobiphenyl	ChEBI
N-1,1'-Biphenyl-4-ylhydroxylamine	ChEBI
N-4-Biphenylylhydroxylamine	ChEBI

Chemical Formula

C₁₂H₁₁NO

Average Molecular Weight

185.226

Monoisotopic Molecular Weight

185.084063978

IUPAC Name

N-{[1,1'-biphenyl]-4-yl}hydroxylamine

Traditional Name

N-hydroxy-4-aminobiphenyl

CAS Registry Number

6810-26-0

SMILES

ONC1=CC=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11NO/c14-13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13-14H

InChI Key

MYVLYOJYVMLSFA-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
N-phenylhydroxylamine
1-hydroxylamino, 2-unsubstituted benzenoid
Arylhydroxamate
N-organohydroxylamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-substituted amine (CHEBI:16580 )
aminobiphenyl (CHEBI:16580 )
a small molecule (N-HYDROXY-4-AMINOBIPHENYL )

Ontology

Not Available

Exogenous (HMDB: HMDB0062723)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.086 g/l	ALOGPS
LogP	2.78	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	5.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.18 m³·mol⁻¹	ChemAxon
Polarizability	20.58 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]+	142.37	31661259
DarkChem	[M-H]-	141.347	31661259
DeepCCS	[M+H]+	141.411	30932474
DeepCCS	[M-H]-	139.015	30932474
DeepCCS	[M-2H]-	174.0	30932474
DeepCCS	[M+Na]+	148.479	30932474
AllCCS	[M+H]+	141.1	32859911
AllCCS	[M+H-H2O]+	136.7	32859911
AllCCS	[M+NH4]+	145.3	32859911
AllCCS	[M+Na]+	146.5	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	142.5	32859911
AllCCS	[M+HCOO]-	142.7	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.	6.19 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6316 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2068.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	484.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	307.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	455.1 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	531.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	160.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1324.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	471.0 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	1021.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	224.7 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	50.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-hydroxy-4-aminobiphenyl	ONC1=CC=C(C=C1)C1=CC=CC=C1	2846.3	Standard polar	33892256
N-hydroxy-4-aminobiphenyl	ONC1=CC=C(C=C1)C1=CC=CC=C1	1944.1	Standard non polar	33892256
N-hydroxy-4-aminobiphenyl	ONC1=CC=C(C=C1)C1=CC=CC=C1	1960.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-hydroxy-4-aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2096.6	Semi standard non polar	33892256
N-hydroxy-4-aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2092.3	Standard non polar	33892256
N-hydroxy-4-aminobiphenyl,1TMS,isomer #1	C[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2473.5	Standard polar	33892256
N-hydroxy-4-aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2358.2	Semi standard non polar	33892256
N-hydroxy-4-aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2271.1	Standard non polar	33892256
N-hydroxy-4-aminobiphenyl,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C1=CC=C(C2=CC=CC=C2)C=C1	2604.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-hydroxy-4-aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1900000000-0db64624bb015df9c8b5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-hydroxy-4-aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-hydroxy-4-aminobiphenyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 10V, Positive-QTOF	splash10-000i-0900000000-d3d4dbf4995491e63d6e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 20V, Positive-QTOF	splash10-000i-0900000000-c97c27170bafb44c24f8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 40V, Positive-QTOF	splash10-0r2j-6900000000-999b1b02a6475d3e8159	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 10V, Negative-QTOF	splash10-001i-0900000000-d07e8c1669db2f0667e7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 20V, Negative-QTOF	splash10-001i-0900000000-14868437d7bba036c261	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 40V, Negative-QTOF	splash10-0zir-4900000000-36c503ebc25578e6fc91	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 10V, Negative-QTOF	splash10-001i-0900000000-58128752be07f02ef3db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 20V, Negative-QTOF	splash10-001i-0900000000-792fb9060135b3481b8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 40V, Negative-QTOF	splash10-0udi-0900000000-abf56cf2f5c228dc0516	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 10V, Positive-QTOF	splash10-000i-0900000000-2473add28d4c43ae79fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 20V, Positive-QTOF	splash10-000i-0900000000-425d2593b44f5a3ad045	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-hydroxy-4-aminobiphenyl 40V, Positive-QTOF	splash10-0f89-0900000000-460675f47f9258e85cd2	2021-09-22	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16580

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-hydroxy-4-aminobiphenyl (HMDB0062723)

MOL for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

3D MOL for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

3D SDF for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

3D-SDF for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

PDB for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

3D PDB for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

SMILES for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

INCHI for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

Structure for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

3D Structure for HMDB0062723 (N-hydroxy-4-aminobiphenyl)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra