Showing metabocard for Formylanthranilic acid (BMDB0004089)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:52 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0004089
Secondary Accession Numbers
  • BMDB04089
Metabolite Identification
Common NameFormylanthranilic acid
DescriptionFormylanthranilic acid, also known as Formylanthranilic acid or Formylanthranilic acid, 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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Formylanthranilic acid exists in all living species, ranging from bacteria to humans. Formylanthranilic acid participates in a number of enzymatic reactions, within cattle. In particular, Formylanthranilic acid and L-alanine can be biosynthesized from n'-formylkynurenine through its interaction with the enzyme kynureninase. In addition, Formylanthranilic acid can be converted into 2-aminobenzoic acid and formic acid; which is mediated by the enzyme kynurenine formamidase. In cattle, formylanthranilic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bj-3900000000-9359f0773784c94dc776View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7960000000-dd39f16e2a1279ad2b63View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-f402423360f439c1a1fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1900000000-a6897d7febc033f7e74bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udu-9500000000-1ebc617a67faf6913fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-4900000000-47ee6a3d468446d91b57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-5bd0ef099bf7ad040444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-9a2518d529a9a3e06c4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-e0f009f502e6b92e8df9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0900000000-b0db1c60ca5f43e28739View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-cf160a89115b4a28e6e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-6bdc8d3e8e4d7dce8972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-55e89d8092accc947316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2acafd816eca326aee0bView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004089
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Kynureninase
General function:
Not Available
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:
F1MCH2
Molecular weight:
52186.0
Reactions
N'-Formylkynurenine + Water → Formylanthranilic acid + L-Alaninedetails
Enzyme Details
2. Kynurenine formamidase
General function:
Not Available
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.
Gene Name:
AFMID
Uniprot ID:
E1BLL5
Molecular weight:
35460.0
Reactions
Formylanthranilic acid + Water → 2-Aminobenzoic acid + Formic aciddetails