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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:20:24 UTC

Update Date

2021-09-26 22:55:19 UTC

HMDB ID

HMDB0246312

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(Phenylamino)benzoic acid

Description

4-(Phenylamino)benzoic acid, also known as fenamic acid or diphenylamine-2-carboxylate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Based on a literature review very few articles have been published on 4-(Phenylamino)benzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(phenylamino)benzoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(Phenylamino)benzoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1652309112101202D          

 16 17  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246312

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=C(NC2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO2/c15-13(16)10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,14H,(H,15,16)

> <INCHI_KEY>
DPAMLADQPZFXMD-UHFFFAOYSA-N

> <FORMULA>
C13H11NO2

> <MOLECULAR_WEIGHT>
213.236

> <EXACT_MASS>
213.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.570265181744094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(phenylamino)benzoic acid

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
3.070754499333333

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.207139736525185

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.648571985165293

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7047249153612348

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
61.80040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(phenylamino)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0246312
HETATM    1  O1  UNL     1       5.480  -0.445  -0.722  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.619   0.367  -0.338  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.977   1.647   0.016  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.234  -0.035  -0.262  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.261   0.843   0.160  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.927   0.437   0.226  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.541  -0.830  -0.120  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.796  -1.257  -0.089  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.954  -0.462  -0.200  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.022   0.770  -0.782  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.221   1.498  -0.819  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.365   0.977  -0.263  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.322  -0.248   0.321  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.140  -0.956   0.353  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.522  -1.699  -0.540  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.855  -1.324  -0.616  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.591   2.091   0.844  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.577   1.841   0.430  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.238   1.177   0.583  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.911  -2.324   0.037  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.138   1.190  -1.242  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.182   2.464  -1.299  1.00  0.00           H  
HETATM   23  H7  UNL     1      -5.270   1.594  -0.324  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.244  -0.633   0.751  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.173  -1.929   0.834  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.296  -2.730  -0.834  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.622  -2.022  -0.949  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   16
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   15
CONECT    8    9   20
CONECT    9   10   10   14
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13   23
CONECT   13   14   14   24
CONECT   14   25
CONECT   15   16   16   26
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Phenylamino)benzoate	Generator
Diphenylamine-2-carboxylate	HMDB
Fenamic acid	HMDB
Diphenylamine carboxylate	HMDB
Diphenylamine-2-carboxylic acid	HMDB
N-Phenylanthranilic acid	HMDB
Fenamic acid, ca salt (2:1)	HMDB
Fenamic acid, monosodium salt	HMDB

Chemical Formula

C₁₃H₁₁NO₂

Average Molecular Weight

213.236

Monoisotopic Molecular Weight

213.078978598

IUPAC Name

4-(phenylamino)benzoic acid

Traditional Name

4-(phenylamino)benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=C(NC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C13H11NO2/c15-13(16)10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,14H,(H,15,16)

InChI Key

DPAMLADQPZFXMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Secondary amine
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.24	ALOGPS
logP	3.07	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.8 m³·mol⁻¹	ChemAxon
Polarizability	22.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.68	30932474
DeepCCS	[M-H]-	144.285	30932474
DeepCCS	[M-2H]-	177.498	30932474
DeepCCS	[M+Na]+	152.593	30932474
AllCCS	[M+H]+	147.6	32859911
AllCCS	[M+H-H2O]+	143.5	32859911
AllCCS	[M+NH4]+	151.4	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	149.7	32859911
AllCCS	[M+Na-2H]-	149.4	32859911
AllCCS	[M+HCOO]-	149.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(Phenylamino)benzoic acid	OC(=O)C1=CC=C(NC2=CC=CC=C2)C=C1	3253.8	Standard polar	33892256
4-(Phenylamino)benzoic acid	OC(=O)C1=CC=C(NC2=CC=CC=C2)C=C1	2143.3	Standard non polar	33892256
4-(Phenylamino)benzoic acid	OC(=O)C1=CC=C(NC2=CC=CC=C2)C=C1	2284.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(Phenylamino)benzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2211.7	Semi standard non polar	33892256
4-(Phenylamino)benzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2218.1	Standard non polar	33892256
4-(Phenylamino)benzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2443.0	Standard polar	33892256
4-(Phenylamino)benzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2693.3	Semi standard non polar	33892256
4-(Phenylamino)benzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2624.5	Standard non polar	33892256
4-(Phenylamino)benzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2669.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0292-1920000000-336f3efffbca0594ac80	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Phenylamino)benzoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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-(Phenylamino)benzoic acid 10V, Positive-QTOF	splash10-03di-0090000000-a440e7873c3dab8cac43	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Phenylamino)benzoic acid 20V, Positive-QTOF	splash10-03di-0290000000-db92ab538466e49bb8e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Phenylamino)benzoic acid 40V, Positive-QTOF	splash10-0v00-3900000000-d0816548cdefe7efc825	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Phenylamino)benzoic acid 10V, Negative-QTOF	splash10-03di-0390000000-874fee63bbda444e4823	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Phenylamino)benzoic acid 20V, Negative-QTOF	splash10-02t9-0950000000-82b904765dd74608b61b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Phenylamino)benzoic acid 40V, Negative-QTOF	splash10-014i-1900000000-5e86a7a599474fe2ca72	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

257959

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

292331

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-(Phenylamino)benzoic acid (HMDB0246312)

MOL for HMDB0246312 (4-(Phenylamino)benzoic acid)

3D MOL for HMDB0246312 (4-(Phenylamino)benzoic acid)

3D SDF for HMDB0246312 (4-(Phenylamino)benzoic acid)

3D-SDF for HMDB0246312 (4-(Phenylamino)benzoic acid)

PDB for HMDB0246312 (4-(Phenylamino)benzoic acid)

3D PDB for HMDB0246312 (4-(Phenylamino)benzoic acid)

SMILES for HMDB0246312 (4-(Phenylamino)benzoic acid)

INCHI for HMDB0246312 (4-(Phenylamino)benzoic acid)

Structure for HMDB0246312 (4-(Phenylamino)benzoic acid)

3D Structure for HMDB0246312 (4-(Phenylamino)benzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra