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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:42 UTC

Update Date

2023-02-21 17:22:26 UTC

HMDB ID

HMDB0032597

Secondary Accession Numbers

HMDB32597

Metabolite Identification

Common Name

4-Hydroxydiphenylamine

Description

4-Hydroxydiphenylamine, also known as N-phenyl-p-aminophenol or p-anilino-phenol, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Based on a literature review very few articles have been published on 4-Hydroxydiphenylamine.

Structure

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


  Mrv0541 05061306352D          

 14 15  0  0  0  0            999 V2000
   -0.7145    2.0625    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    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    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032597

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(NC2=CC=CC=C2)C=C1

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

> <INCHI_KEY>
JTTMYKSFKOOQLP-UHFFFAOYSA-N

> <FORMULA>
C12H11NO

> <MOLECULAR_WEIGHT>
185.2218

> <EXACT_MASS>
185.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.24728621732949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(phenylamino)phenol

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.1096062696666658

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.974950861373802

> <JCHEM_PKA_STRONGEST_BASIC>
2.1713326255794625

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
56.52510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenol, 4-(phenylamino)-

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   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      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+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   13                                                  
CONECT   11    6    7   13                                                  
CONECT   12    8    9   14                                                  
CONECT   13   10   11                                                       
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Phenylamino)-phenol	HMDB
4-(Phenylamino)phenol, 9ci	HMDB
4-Anilinophenol	HMDB
4-Hydroxy-diphenylamine	HMDB
4-Hydroxy-N-phenylaniline	HMDB
4-Phenylaminophenol	HMDB
AMINE,diphenyl,4-hydroxy	HMDB
N-Phenyl-p-aminophenol	HMDB
p-(Phenylamino)phenol	HMDB
p-Anilino-phenol	HMDB
p-Anilinophenol	HMDB
p-Hydroxydifenylamin	HMDB
p-Hydroxydiphenylamine	HMDB
p-Oxydiphenylamine	HMDB
Para-hydroxydifenylamin	HMDB
Phenyl-p-aminophenol	HMDB
VTI 1	HMDB

Chemical Formula

C₁₂H₁₁NO

Average Molecular Weight

185.2218

Monoisotopic Molecular Weight

185.084063979

IUPAC Name

4-(phenylamino)phenol

Traditional Name

phenol, 4-(phenylamino)-

CAS Registry Number

122-37-2

SMILES

OC1=CC=C(NC2=CC=CC=C2)C=C1

InChI Identifier

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

InChI Key

JTTMYKSFKOOQLP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

P-aminophenol
Aniline or substituted anilines
Aminophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032597)
Cell membrane (HMDB: HMDB0032597)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032597)

Source

Endogenous

Endogenous (HMDB: HMDB0032597)

Plant

Plant (HMDB: HMDB0032597)

Exogenous

Food

Food (HMDB: HMDB0032597)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	73 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.82	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	2.17	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	56.53 m³·mol⁻¹	ChemAxon
Polarizability	20.25 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]+	142.478	31661259
DarkChem	[M-H]-	142.021	31661259
DeepCCS	[M+H]+	137.417	30932474
DeepCCS	[M-H]-	135.021	30932474
DeepCCS	[M-2H]-	170.475	30932474
DeepCCS	[M+Na]+	144.934	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	145.1	32859911
AllCCS	[M+Na]+	146.2	32859911
AllCCS	[M-H]-	142.2	32859911
AllCCS	[M+Na-2H]-	142.2	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxydiphenylamine	OC1=CC=C(NC2=CC=CC=C2)C=C1	2821.7	Standard polar	33892256
4-Hydroxydiphenylamine	OC1=CC=C(NC2=CC=CC=C2)C=C1	1912.7	Standard non polar	33892256
4-Hydroxydiphenylamine	OC1=CC=C(NC2=CC=CC=C2)C=C1	1977.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxydiphenylamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(NC2=CC=CC=C2)C=C1	2026.5	Semi standard non polar	33892256
4-Hydroxydiphenylamine,1TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(O)C=C1	2017.0	Semi standard non polar	33892256
4-Hydroxydiphenylamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	1986.5	Semi standard non polar	33892256
4-Hydroxydiphenylamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	1964.3	Standard non polar	33892256
4-Hydroxydiphenylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(NC2=CC=CC=C2)C=C1	2286.9	Semi standard non polar	33892256
4-Hydroxydiphenylamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(O)C=C1	2243.1	Semi standard non polar	33892256
4-Hydroxydiphenylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2442.7	Semi standard non polar	33892256
4-Hydroxydiphenylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2409.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydiphenylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1900000000-46e10f99cc234eb8ac44	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydiphenylamine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9860000000-ce10e5ac849e26803a4e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydiphenylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydiphenylamine 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 - 4-Hydroxydiphenylamine 10V, Positive-QTOF	splash10-000i-0900000000-cc4585bda564eaa2c482	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 20V, Positive-QTOF	splash10-000i-0900000000-a390b4eb8bfd3a46cf27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 40V, Positive-QTOF	splash10-0gb9-7900000000-46f0a4aab0549ee46ea1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 10V, Negative-QTOF	splash10-001i-0900000000-0faab16ef645c03c2957	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 20V, Negative-QTOF	splash10-001i-0900000000-18a6aeaf333d90fa4e8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 40V, Negative-QTOF	splash10-00nf-6900000000-2d562e7a09f2237635c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 10V, Positive-QTOF	splash10-000i-0900000000-2473add28d4c43ae79fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 20V, Positive-QTOF	splash10-000i-0900000000-2473add28d4c43ae79fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 40V, Positive-QTOF	splash10-003r-5900000000-9b219ba22a5874628338	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 10V, Negative-QTOF	splash10-001i-0900000000-58128752be07f02ef3db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 20V, Negative-QTOF	splash10-001i-0900000000-abedee1e891a819ca695	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydiphenylamine 40V, Negative-QTOF	splash10-00lu-3900000000-1539b6a0e7c1ba2eb40b	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]-)	2023-02-04	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

Membrane

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

FDB010535

KNApSAcK ID

Not Available

Chemspider ID

21111849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31208

PDB ID

Not Available

ChEBI ID

Not Available

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxydiphenylamine (HMDB0032597)

MOL for HMDB0032597 (4-Hydroxydiphenylamine)

3D MOL for HMDB0032597 (4-Hydroxydiphenylamine)

3D SDF for HMDB0032597 (4-Hydroxydiphenylamine)

3D-SDF for HMDB0032597 (4-Hydroxydiphenylamine)

PDB for HMDB0032597 (4-Hydroxydiphenylamine)

3D PDB for HMDB0032597 (4-Hydroxydiphenylamine)

SMILES for HMDB0032597 (4-Hydroxydiphenylamine)

INCHI for HMDB0032597 (4-Hydroxydiphenylamine)

Structure for HMDB0032597 (4-Hydroxydiphenylamine)

3D Structure for HMDB0032597 (4-Hydroxydiphenylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra