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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:37:45 UTC
Update Date2022-09-22 18:34:18 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). An amidobenzoic acid consisting of anthranilic acid carrying an N-formyl group. 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 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 humans, formylanthranilic acid is involved in tryptophan metabolism.
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg127.2830932474
[M-H]-Not Available127.28http://allccs.zhulab.cn/database/detail?ID=AllCCS00000306
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.7831661259
DarkChem[M-H]-131.45631661259
DeepCCS[M+H]+133.62630932474
DeepCCS[M-H]-131.01330932474
DeepCCS[M-2H]-167.00430932474
DeepCCS[M+Na]+142.17530932474
AllCCS[M+H]+135.432859911
AllCCS[M+H-H2O]+131.032859911
AllCCS[M+NH4]+139.532859911
AllCCS[M+Na]+140.632859911
AllCCS[M-H]-130.532859911
AllCCS[M+Na-2H]-131.532859911
AllCCS[M+HCOO]-132.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Formylanthranilic acidOC(=O)C1=CC=CC=C1NC=O2863.3Standard polar33892256
Formylanthranilic acidOC(=O)C1=CC=CC=C1NC=O1722.9Standard non polar33892256
Formylanthranilic acidOC(=O)C1=CC=CC=C1NC=O1740.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Formylanthranilic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1NC=O1694.7Semi standard non polar33892256
Formylanthranilic acid,1TMS,isomer #2C[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)O1689.4Semi standard non polar33892256
Formylanthranilic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C1684.1Semi standard non polar33892256
Formylanthranilic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C1808.6Standard non polar33892256
Formylanthranilic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C1969.7Standard polar33892256
Formylanthranilic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC=O1951.6Semi standard non polar33892256
Formylanthranilic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)O1924.5Semi standard non polar33892256
Formylanthranilic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C2131.0Semi standard non polar33892256
Formylanthranilic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C2157.7Standard non polar33892256
Formylanthranilic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C2254.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Formylanthranilic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bj-3900000000-9359f0773784c94dc7762016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formylanthranilic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7960000000-dd39f16e2a1279ad2b632017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formylanthranilic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formylanthranilic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 10V, Positive-QTOFsplash10-00kr-0900000000-f402423360f439c1a1fc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 20V, Positive-QTOFsplash10-0079-1900000000-a6897d7febc033f7e74b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 40V, Positive-QTOFsplash10-0udu-9500000000-1ebc617a67faf6913fe62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 10V, Negative-QTOFsplash10-03mi-4900000000-47ee6a3d468446d91b572016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 20V, Negative-QTOFsplash10-006x-8900000000-5bd0ef099bf7ad0404442016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 40V, Negative-QTOFsplash10-002f-9200000000-9a2518d529a9a3e06c4d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 10V, Positive-QTOFsplash10-00di-0900000000-e0f009f502e6b92e8df92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 20V, Positive-QTOFsplash10-00dj-0900000000-b0db1c60ca5f43e287392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 40V, Positive-QTOFsplash10-00di-5900000000-cf160a89115b4a28e6e82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 10V, Negative-QTOFsplash10-00di-3900000000-6bdc8d3e8e4d7dce89722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 20V, Negative-QTOFsplash10-0006-9300000000-55e89d8092accc9473162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formylanthranilic acid 40V, Negative-QTOFsplash10-0006-9000000000-2acafd816eca326aee0b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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 IDNFORMANTH
MarkerDB IDNot Available
Good Scents 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