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Showing metabocard for 2-Aminobenzoic acid (HMDB0001123)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:27 UTC
HMDB IDHMDB0001123
Secondary Accession Numbers
  • HMDB01123
Metabolite Identification
Common Name2-Aminobenzoic acid
Description2-Aminobenzoic acid, also known as anthranilic acid or O-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Within humans, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, 2-aminobenzoic acid and formic acid can be biosynthesized from formylanthranilic acid through its interaction with the enzyme kynurenine formamidase. In addition, 2-aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through its interaction with the enzyme kynureninase. It is a substrate of enzyme 2-Aminobenzoic acid hydroxylase in benzoate degradation via hydroxylation pathway (KEGG). In humans, 2-aminobenzoic acid is involved in tryptophan metabolism. Outside of the human body, 2-Aminobenzoic acid has been detected, but not quantified in several different foods, such as mamey sapotes, prairie turnips, rowals, natal plums, and hyacinth beans. This could make 2-aminobenzoic acid a potential biomarker for the consumption of these foods. 2-Aminobenzoic acid is a is a tryptophan-derived uremic toxin with multidirectional properties that can affect the hemostatic system. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001123 (2-Aminobenzoic acid)

  Mrv1652309042000182D          

 10 10  0  0  0  0            999 V2000
    1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 N   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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
M  END
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3D MOL for HMDB0001123 (2-Aminobenzoic acid)

HMDB0001123
     RDKit          3D
2-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.4672   -1.5995    0.4589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919   -0.9279    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -1.5987   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118   -0.8630   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351    0.5041   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362    1.1799   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936    0.4672    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4389    1.1794    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604    0.5713    0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4359    2.5542    0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633   -1.8076    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -1.8988   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -2.6863   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861   -1.4049   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420    1.0022   -1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    2.2632   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    3.0651    1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0001123 (2-Aminobenzoic acid)

  Mrv1652309042000182D          

 10 10  0  0  0  0            999 V2000
    1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 N   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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001123

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)

> <INCHI_KEY>
RWZYAGGXGHYGMB-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.288743336988986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminobenzoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
1.4519027699999998

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.44069433947566

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.892673611619119

> <JCHEM_PKA_STRONGEST_BASIC>
1.9474348350285466

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
38.0146

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminobenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001123 (2-Aminobenzoic acid)

HMDB0001123
     RDKit          3D
2-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.4672   -1.5995    0.4589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919   -0.9279    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -1.5987   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118   -0.8630   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351    0.5041   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362    1.1799   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936    0.4672    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4389    1.1794    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604    0.5713    0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4359    2.5542    0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5633   -1.8076    1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -1.8988   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -2.6863   -0.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861   -1.4049   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420    1.0022   -1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    2.2632   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    3.0651    1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0001123 (2-Aminobenzoic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667   1.925   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.667   2.695   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.001   2.695   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -2.001   0.385   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0001123 (2-Aminobenzoic acid)

COMPND    HMDB0001123
HETATM    1  N1  UNL     1      -1.467  -1.599   0.459  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.292  -0.928   0.023  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.816  -1.599  -0.447  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.912  -0.863  -0.848  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.935   0.504  -0.795  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.836   1.180  -0.328  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.294   0.467   0.087  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.439   1.179   0.574  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.460   0.571   0.952  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.436   2.554   0.636  1.00  0.00           O  
HETATM   11  H1  UNL     1      -1.563  -1.808   1.487  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.238  -1.899  -0.170  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.801  -2.686  -0.490  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.786  -1.405  -1.219  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.842   1.002  -1.132  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.863   2.263  -0.289  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.602   3.065   1.500  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   17
END
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SMILES for HMDB0001123 (2-Aminobenzoic acid)

NC1=CC=CC=C1C(O)=O
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INCHI for HMDB0001123 (2-Aminobenzoic acid)

InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H7NO2
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name2-aminobenzoic acid
Traditional Name2-aminobenzoic acid
CAS Registry Number118-92-3
SMILES
NC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyRWZYAGGXGHYGMB-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.5 mg/mLNot Available
LogP1.21HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available125.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000295
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.12 +/- 0.05 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified17.78 +/- 18.028 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB04166
Phenol Explorer Compound IDNot Available
FooDB IDFDB000896
KNApSAcK IDC00007382
Chemspider ID222
KEGG Compound IDC00108
BioCyc IDANTHRANILATE
BiGG ID33883
Wikipedia LinkAnthranilic_acid
METLIN ID6018
PubChem Compound227
PDB IDNot Available
ChEBI ID30754
Food Biomarker OntologyNot Available
VMH IDANTH
MarkerDB IDMDB00000301
Good Scents IDNot Available
References
Synthesis ReferenceWang, Chengyin; Yang, Jisheng; Wang, Honghai. Production of o-aminobenzoic acid from by-product o-nitrobenzoic acid. Huaxue Shijie (1999), 40(5), 274-277.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Kynureninase
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
Reactions
Kynurenine + Water → 2-Aminobenzoic acid + L-Alaninedetails
Enzyme Details
2. Kynurenine formamidase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5
Reactions
Formylanthranilic acid + Water → Formic acid + 2-Aminobenzoic aciddetails