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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:37:45 UTC
Update Date2020-02-26 21:24:58 UTC
HMDB IDHMDB0004089
Secondary Accession Numbers
  • HMDB04089
Metabolite Identification
Common NameFormylanthranilic acid
DescriptionFormylanthranilic acid, also known as N-formylanthranilate or 2-(formylamino)-benzoate, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Formylanthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Formylanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, formylanthranilic acid participates in a number of enzymatic reactions. In particular, formylanthranilic acid and L-alanine can be biosynthesized from n'-formylkynurenine; which is mediated by the enzyme kynureninase. In addition, formylanthranilic acid can be converted into 2-aminobenzoic acid and formic acid through the action of the enzyme kynurenine formamidase. In humans, formylanthranilic acid is involved in tryptophan metabolism. Formylanthranilic acid is a polar acid metabolite of anthranilic acid, occasionally found in human urine.
Structure
Data?1582752298
Synonyms
ValueSource
2-(Formylamino)-benzoic acidChEBI
2-(Formylamino)benzoic acidChEBI
N-FormylanthranilateKegg
2-(Formylamino)-benzoateGenerator
2-(Formylamino)benzoateGenerator
N-Formylanthranilic acidGenerator
FormylanthranilateGenerator
2-FormamidobenzoateHMDB
2-Formamidobenzoic acidHMDB
Chemical FormulaC8H7NO3
Average Molecular Weight165.1461
Monoisotopic Molecular Weight165.042593095
IUPAC Name2-formamidobenzoic acid
Traditional Nameformylanthranilic acid
CAS Registry Number3342-77-6
SMILES
OC(=O)C1=CC=CC=C1NC=O
InChI Identifier
InChI=1S/C8H7NO3/c10-5-9-7-4-2-1-3-6(7)8(11)12/h1-5H,(H,9,10)(H,11,12)
InChI KeyLLLPDUXGHXIXIW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.33 g/LALOGPS
logP0.28ALOGPS
logP1.47ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.69 m³·mol⁻¹ChemAxon
Polarizability15.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bj-3900000000-9359f0773784c94dc776Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7960000000-dd39f16e2a1279ad2b63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-f402423360f439c1a1fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1900000000-a6897d7febc033f7e74bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udu-9500000000-1ebc617a67faf6913fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-4900000000-47ee6a3d468446d91b57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-5bd0ef099bf7ad040444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-9a2518d529a9a3e06c4dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023309
KNApSAcK IDNot Available
Chemspider ID91624
KEGG Compound IDC05653
BioCyc IDNot Available
BiGG ID46205
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101399
PDB IDNot Available
ChEBI ID36575
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferencePrashad, Mahavir; Har, Denis; Repic, Oljan; Blacklock, Thomas J.; Chin, Jefferson A.; Shapiro, Michael J. Reaction of benzoyleneurea and isatoic anhydride with the Vilsmeier reagent. Tetrahedron Letters (1997), 38(8), 1313-1316.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [PubMed:7320161 ]

Enzymes

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
L-Formylkynurenine + Water → Formylanthranilic acid + L-Alaninedetails
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