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Showing metabocard for 2-Aminobenzoic acid (HMDB0001123)

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enzymes (2) Show 2 proteins
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
Data?1676999727
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
Download

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
Download

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
ValueSource
2-AminobenzoesaeureChEBI
2-CarboxyanilineChEBI
O-AminobenzoesaeureChEBI
O-Aminobenzoic acidChEBI
O-CarboxyanilineChEBI
Vitamin L1ChEBI
Anthranilic acidKegg
2-AminobenzoateKegg
O-AminobenzoateGenerator
AnthranilateGenerator
Anthranilic acid, cadmium saltHMDB
Anthranilic acid, calcium (2:1) saltHMDB
Anthranilic acid, monolithium saltHMDB
Sodium anthranilateHMDB
Anthranilic acid, dihydrochlorideHMDB
Anthranilic acid, hydrochlorideHMDB
Anthranilic acid, monosodium saltHMDB
1-Amino-2-carboxybenzeneHMDB
2-Amino-benzoateHMDB
2-Amino-benzoic acidHMDB
2-AminophenylacetateHMDB
2-Aminophenylacetic acidHMDB
AnthranateHMDB
Anthranic acidHMDB
Anthranilic acid GRHMDB
CarboxyanilineHMDB
H-2-Abz-OHHMDB
Kyselina anthranilovaHMDB
Kyselina O-aminobenzoovaHMDB
O-Amino-benzoateHMDB
O-Amino-benzoic acidHMDB
O-AnthranilateHMDB
O-Anthranilic acidHMDB
Ortho-amidobenzoateHMDB
Ortho-amidobenzoic acidHMDB
Ortho-aminobenzoateHMDB
Ortho-aminobenzoic acidHMDB
Vitamin LHMDB
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
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP0.78ALOGPS
logP1.45ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.3831661259
DarkChem[M-H]-122.0931661259
AllCCS[M+H]+129.48732859911
AllCCS[M-H]-124.41232859911
DeepCCS[M+H]+127.13730932474
DeepCCS[M-H]-123.54630932474
DeepCCS[M-2H]-160.46930932474
DeepCCS[M+Na]+135.730932474
AllCCS[M+H]+129.532859911
AllCCS[M+H-H2O]+124.832859911
AllCCS[M+NH4]+133.832859911
AllCCS[M+Na]+135.132859911
AllCCS[M-H]-124.432859911
AllCCS[M+Na-2H]-126.132859911
AllCCS[M+HCOO]-127.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.2.38 minutes32390414
Predicted by Siyang on May 30, 202210.3603 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.0 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid60.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1062.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid351.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid81.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid211.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid70.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid280.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid347.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)148.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid755.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid201.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid930.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid229.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid301.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate473.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA213.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water178.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Aminobenzoic acidNC1=CC=CC=C1C(O)=O2949.1Standard polar33892256
2-Aminobenzoic acidNC1=CC=CC=C1C(O)=O1443.7Standard non polar33892256
2-Aminobenzoic acidNC1=CC=CC=C1C(O)=O1447.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Aminobenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N1498.0Semi standard non polar33892256
2-Aminobenzoic acid,1TMS,isomer #2C[Si](C)(C)NC1=CC=CC=C1C(=O)O1607.4Semi standard non polar33892256
2-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C1600.8Semi standard non polar33892256
2-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C1634.8Standard non polar33892256
2-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C1778.7Standard polar33892256
2-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C1660.6Semi standard non polar33892256
2-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C1772.2Standard non polar33892256
2-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C1839.3Standard polar33892256
2-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1633.8Semi standard non polar33892256
2-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1731.4Standard non polar33892256
2-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1712.5Standard polar33892256
2-Aminobenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N1747.5Semi standard non polar33892256
2-Aminobenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)O1858.5Semi standard non polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2045.2Semi standard non polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2031.4Standard non polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2087.6Standard polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C2085.5Semi standard non polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C2140.7Standard non polar33892256
2-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C2058.6Standard polar33892256
2-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2278.8Semi standard non polar33892256
2-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2301.9Standard non polar33892256
2-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2116.6Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.001 +/- 0.000046 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.03 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.001 +/- 0.00027 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.42 (0.15-1.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.12 +/- 0.05 uMAdult (>18 years old)Bothuremia 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
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)Download (PDF)
General References
  1. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]
  2. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
  3. Di Marco GS, Quinto BM, Juliano M, Carmona AK, Stella RC, Plavnik FL, Casarini DE: Purification and characterization of a neutral endopeptidase-like enzyme from human urine. J Hypertens. 1998 Dec;16(12 Pt 2):1971-8. [PubMed:9886885 ]
  4. Hagag N, Birnbaum ER, Darnall DW: Resonance energy transfer between cysteine-34, tryptophan-214, and tyrosine-411 of human serum albumin. Biochemistry. 1983 May 10;22(10):2420-7. [PubMed:6860638 ]
  5. Little CH, Georgiou GM, Shelton MJ, Simpson F, Cone RE: Clinical and immunological responses in subjects sensitive to solvents. Arch Environ Health. 1999 Jan-Feb;54(1):6-14. [PubMed:10025410 ]
  6. Ritchie MR, Morton MS, Thompson AM, Deighton N, Blake A, Cummings JH, Steel CM: Investigation of the reliability of 24 h urine excretion as a biomarker of isoflavone exposure over time and over a wide range of isoflavone intakes. Eur J Clin Nutr. 2004 Sep;58(9):1286-9. [PubMed:15054404 ]
  7. Ortega RM, Andres P, Martinez RM, Lopez-Sobaler AM: Vitamin A status during the third trimester of pregnancy in Spanish women: influence on concentrations of vitamin A in breast milk. Am J Clin Nutr. 1997 Sep;66(3):564-8. [PubMed:9280174 ]
  8. Alves MF, Araujo MC, Juliano MA, Oliveira EM, Krieger JE, Casarini DE, Juliano L, Carmona AK: A continuous fluorescent assay for the determination of plasma and tissue angiotensin I-converting enzyme activity. Braz J Med Biol Res. 2005 Jun;38(6):861-8. Epub 2005 Jun 1. [PubMed:15933779 ]
  9. Soma J, Sugawara T, Huang YD, Nakajima J, Kawamura M: Tranilast slows the progression of advanced diabetic nephropathy. Nephron. 2002;92(3):693-8. [PubMed:12372957 ]
  10. Ahmad S: The functional roles of cytochrome P-450 mediated systems: present knowledge and future areas of investigations. Drug Metab Rev. 1979;10(1):1-14. [PubMed:118858 ]
  11. Spivak W, Carey MC: Reverse-phase h.p.l.c. separation, quantification and preparation of bilirubin and its conjugates from native bile. Quantitative analysis of the intact tetrapyrroles based on h.p.l.c. of their ethyl anthranilate azo derivatives. Biochem J. 1985 Feb 1;225(3):787-805. [PubMed:3919713 ]
  12. 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 ]

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