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Identification
YMDB IDYMDB00254
Name3-Hydroxyanthranilic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a strong basic compound (based on its pKa). 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within yeast, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, L-alanine and 3-hydroxyanthranilic acid can be biosynthesized from 3-hydroxy-L-kynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into 2-amino-3-carboxymuconic acid semialdehyde through the action of the enzyme 3-hydroxyanthranilate 3,4-dioxygenase. In yeast, 3-hydroxyanthranilic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
Synonyms
  • 2-amino-3-hydroxy-Benzoate
  • 2-amino-3-hydroxy-Benzoic acid
  • 2-Amino-3-hydroxybenzoate
  • 2-Amino-3-hydroxybenzoic acid
  • 3-hydroxanthranilate
  • 3-Hydroxy-2-aminobenzoate
  • 3-Hydroxy-2-aminobenzoic acid
  • 3-hydroxy-Anthranilate
  • 3-hydroxy-Anthranilic acid
  • 3-Hydroxy-anthranilsaeure
  • 3-Hydroxyanthranilate
  • 3-hydroxyanthranilic acid
  • 3-hydroxyantranilic acid
  • 3-OH-anthranilic acid
  • 3-OHAA
  • 3-Oxyanthranilate
  • 3-Oxyanthranilic acid
  • Anthranilic acid, 3-hydroxy-
  • Benzoic acid, 2-amino-3-hydroxy-
  • 3 Hydroxyanthranilic acid
  • Acid, 3-hydroxyanthranilic
CAS number548-93-6
WeightAverage: 153.1354
Monoisotopic: 153.042593095
InChI KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
InChIInChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
IUPAC Name2-amino-3-hydroxybenzoic acid
Traditional IUPAC Name3-hydroxyanthranilic acid
Chemical FormulaC7H7NO3
SMILES[H]OC(=O)C1=C([H])C([H])=C([H])C(O[H])=C1N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.81ALOGPS
logP1.15ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
3-Hydroxyanthranilic acid + oxygenhydron + 2-Amino-3-carboxymuconic acid semialdehyde
L-3-Hydroxykynurenine + waterL-Alanine + hydron + 3-Hydroxyanthranilic acid
KEGG Reactions
L-3-Hydroxykynurenine + water3-Hydroxyanthranilic acid + L-Alanine
3-Hydroxyanthranilic acid + oxygen2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfv-0945000000-e3389ab25b7133eb184dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1955000000-fd51cc45bf09750e2b48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfv-0945000000-e3389ab25b7133eb184dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfu-1955000000-fd51cc45bf09750e2b48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfv-0934000000-11e2b38a36cb364bcaf3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0920000000-a57d310e9ca51aefd0c1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-2900000000-f4f0b5c84821e81f2eeaJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-6390000000-71ab4928435b01bf5b59JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2313e347dd8659099393JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-4e342fdebc8145b606a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-ee5255b437ae762be1f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000t-2900000000-a68dc7ca20e1f9595f15JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-ced0a738a11057bc94e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-cded3154e50c6169c670JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-9c388fc3035f19e3f156JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-9dbb06a7728aab173e0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-19cfe2cda31cf7284669JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-02ae2bd70b54df77aca5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-56e21a4ececd5541a7d8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-0900000000-e3015612b3d263fabaa9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a5i-3900000000-670c7d91a38e852d8e4cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-5900000000-36b3a876d06807eb22a3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-84ae4ad8e91e8e4b6a6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-1900000000-6695f66ad1f45898b8b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9300000000-43045627b8c856bf07d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-810a4a12ecb151ecb516JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-9f194909a88a4ac248b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-608d595690e7902b6195JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kucharczyk, R., Zagulski, M., Rytka, J., Herbert, C. J. (1998). "The yeast gene YJR025c encodes a 3-hydroxyanthranilic acid dioxygenase and is involved in nicotinic acid biosynthesis." FEBS Lett 424:127-130.9539135
  • Lesuisse, E., Simon, M., Klein, R., Labbe, P. (1992). "Excretion of anthranilate and 3-hydroxyanthranilate by Saccharomyces cerevisiae: relationship to iron metabolism." J Gen Microbiol 138:85-89.1556559
Synthesis Reference:Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.
External Links:
ResourceLink
CHEBI ID15793
HMDB IDHMDB01476
Pubchem Compound ID86
Kegg IDC00632
ChemSpider ID84
FOODB IDFDB010582
Wikipedia3-Hydroxyanthranilic_acid
BioCyc ID3-HYDROXY-ANTHRANILATE

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
Gene Name:
BNA5
Uniprot ID:
Q05979
Molecular weight:
51031.60156
Reactions
L-kynurenine + H(2)O → anthranilate + L-alanine.
L-3-hydroxykynurenine + H(2)O → 3-hydroxyanthranilate + L-alanine.
General function:
Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:
Catalyzes the oxidative ring opening of 3- hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate
Gene Name:
BNA1
Uniprot ID:
P47096
Molecular weight:
20234.90039
Reactions
3-hydroxyanthranilate + O(2) → 2-amino-3-carboxymuconate semialdehyde.