You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:48:15 UTC

Update Date

2021-09-26 23:09:51 UTC

HMDB ID

HMDB0255225

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-phenylanthranilic acid

Description

fenamic acid, also known as DPC or 2-anilinobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. fenamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). N-phenylanthranilic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-phenylanthranilic 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


  Mrv1652306031606192D          

 16 17  0  0  0  0            999 V2000
    3.5724   -0.4125    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
    2.8579    0.0000    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    2.4750    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    3.3000    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255225

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1NC1=CC=CC=C1

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

> <INCHI_KEY>
ZWJINEZUASEZBH-UHFFFAOYSA-N

> <FORMULA>
C13H11NO2

> <MOLECULAR_WEIGHT>
213.236

> <EXACT_MASS>
213.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.2313795415182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(phenylamino)benzoic acid

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
4.370754499333334

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.94553035564897

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8841086820097557

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6442244553038599

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
61.80040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylanthranilic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6    7   14                                                  
CONECT   11    8   12   13                                                  
CONECT   12    9   11   14                                                  
CONECT   13   11   15   16                                                  
CONECT   14   10   12                                                       
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0255225
HETATM    1  O1  UNL     1      -3.731   2.234   0.986  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.510   1.896   0.776  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.567   2.823   1.077  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.298   0.570   0.249  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.399  -0.284   0.036  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.289  -1.556  -0.426  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.035  -2.047  -0.706  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.936  -1.236  -0.511  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.044   0.083  -0.031  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.132   0.861   0.067  1.00  0.00           N  
HETATM   11  C8  UNL     1       1.453   0.320   0.084  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.802  -0.856   0.707  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.101  -1.307   0.637  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.032  -0.571  -0.058  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.700   0.606  -0.686  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.406   1.055  -0.616  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.533   3.701   0.595  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.376   0.103   0.256  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.138  -2.219  -0.591  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.939  -3.066  -1.077  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.035  -1.618  -0.756  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.044   1.892   0.113  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.066  -1.422   1.272  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.380  -2.237   1.129  1.00  0.00           H  
HETATM   25  H9  UNL     1       5.070  -0.905  -0.131  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.452   1.192  -1.242  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.123   1.988  -1.109  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10
CONECT   10   11   22
CONECT   11   12   12   16
CONECT   12   13   23
CONECT   13   14   14   24
CONECT   14   15   25
CONECT   15   16   16   26
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Anilinobenzoic acid	ChEBI
2-Carboxydiphenylamine	ChEBI
Diphenylamine-2-carboxylic acid	ChEBI
DPC	ChEBI
N-Phenyl-ortho-aminobenzoic acid	ChEBI
N-Phenylanthranilic acid	ChEBI
Ortho-anilinobenzoic acid	ChEBI
Phenylanthranilic acid	ChEBI
2-Anilinobenzoate	Generator
Diphenylamine-2-carboxylate	Generator
N-Phenyl-ortho-aminobenzoate	Generator
N-Phenylanthranilate	Generator
Ortho-anilinobenzoate	Generator
Phenylanthranilate	Generator
Fenamate	Generator
4-(Phenylamino)benzoic acid	MeSH
Diphenylamine carboxylate	MeSH
Fenamic acid	MeSH
Fenamic acid, ca salt (2:1)	MeSH
Fenamic acid, monosodium salt	MeSH

Chemical Formula

C₁₃H₁₁NO₂

Average Molecular Weight

213.236

Monoisotopic Molecular Weight

213.078978598

IUPAC Name

2-(phenylamino)benzoic acid

Traditional Name

phenylanthranilic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC=C1NC1=CC=CC=C1

InChI Identifier

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

InChI Key

ZWJINEZUASEZBH-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
Vinylogous amide
Amino acid or derivatives
Amino acid
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:34756 )
aminobenzoic acid (CHEBI:34756 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	4.19	ALOGPS
logP	4.37	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-1.6	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	22.23 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]+	144.801	30932474
DeepCCS	[M-H]-	142.405	30932474
DeepCCS	[M-2H]-	176.249	30932474
DeepCCS	[M+Na]+	150.91	30932474
AllCCS	[M+H]+	147.1	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	147.7	32859911
AllCCS	[M+Na-2H]-	147.4	32859911
AllCCS	[M+HCOO]-	147.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-phenylanthranilic acid	OC(=O)C1=CC=CC=C1NC1=CC=CC=C1	3122.0	Standard polar	33892256
N-phenylanthranilic acid	OC(=O)C1=CC=CC=C1NC1=CC=CC=C1	2070.9	Standard non polar	33892256
N-phenylanthranilic acid	OC(=O)C1=CC=CC=C1NC1=CC=CC=C1	2018.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-phenylanthranilic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C	1963.2	Semi standard non polar	33892256
N-phenylanthranilic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C	2107.0	Standard non polar	33892256
N-phenylanthranilic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C	2397.1	Standard polar	33892256
N-phenylanthranilic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2389.8	Semi standard non polar	33892256
N-phenylanthranilic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2462.2	Standard non polar	33892256
N-phenylanthranilic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2628.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0292-1910000000-371b06233a1c34c1c3b5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-phenylanthranilic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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-phenylanthranilic acid 10V, Positive-QTOF	splash10-03dj-0890000000-8d57bd6f9351e396e0e4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-phenylanthranilic acid 20V, Positive-QTOF	splash10-0002-0920000000-28ea0b21e8c672a8018c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-phenylanthranilic acid 40V, Positive-QTOF	splash10-0udj-6900000000-04ae1d2c3ef50ec14c2a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-phenylanthranilic acid 10V, Negative-QTOF	splash10-02t9-0960000000-3fe4cdc1d906d857b94e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-phenylanthranilic acid 20V, Negative-QTOF	splash10-014i-0910000000-29af572020b64e41996a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-phenylanthranilic acid 40V, Negative-QTOF	splash10-014i-0900000000-0a3058525888072807db	2019-02-23	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

Not Available

KEGG Compound ID

C13697

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenamic_acid

METLIN ID

Not Available

PubChem Compound

4386

PDB ID

Not Available

ChEBI ID

34756

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 N-phenylanthranilic acid (HMDB0255225)

MOL for HMDB0255225 (N-phenylanthranilic acid)

3D MOL for HMDB0255225 (N-phenylanthranilic acid)

3D SDF for HMDB0255225 (N-phenylanthranilic acid)

3D-SDF for HMDB0255225 (N-phenylanthranilic acid)

PDB for HMDB0255225 (N-phenylanthranilic acid)

3D PDB for HMDB0255225 (N-phenylanthranilic acid)

SMILES for HMDB0255225 (N-phenylanthranilic acid)

INCHI for HMDB0255225 (N-phenylanthranilic acid)

Structure for HMDB0255225 (N-phenylanthranilic acid)

3D Structure for HMDB0255225 (N-phenylanthranilic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra