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Record Information
Version3.6
Creation Date2006-08-13 10:37:45 UTC
Update Date2016-02-11 01:06:34 UTC
HMDB IDHMDB04089
Secondary Accession NumbersNone
Metabolite Identification
Common NameFormylanthranilic acid
DescriptionFormylanthranilic acid is a polar acid metabolite of anthranilic acid, occasionally found in human urine. (PMID 7320161 ).
Structure
Thumb
Synonyms
ValueSource
2-(formylamino)-Benzoic acidChEBI
2-(formylamino)Benzoic acidChEBI
2-(formylamino)-BenzoateGenerator
2-FormamidobenzoateGenerator
2-(formylamino)BenzoateGenerator
FormylanthranilateHMDB
N-FormylanthranilateHMDB
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 KeyInChIKey=LLLPDUXGHXIXIW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
logP0.28ALOGPS
logP1.47ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.69 m3·mol-1ChemAxon
Polarizability15.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023309
KNApSAcK IDNot Available
Chemspider ID91624
KEGG Compound IDC05653
BioCyc IDNot Available
BiGG ID46205
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04089
Metagene LinkHMDB04089
METLIN IDNot Available
PubChem Compound101399
PDB IDNot Available
ChEBI ID36575
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. [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