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Record Information
Version	2.0
Creation Date	2012-05-31 13:53:13 -0600
Update Date	2015-09-13 12:56:11 -0600
Secondary Accession Numbers	ECMDB01476
Identification
Name:	3-Hydroxyanthranilic acid
Description	3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xabfe305c> Close
Synonyms:	2-Amino-3-hydroxy-Benzoate 2-Amino-3-hydroxy-Benzoic acid 2-Amino-3-hydroxybenzoate 2-Amino-3-hydroxybenzoic acid 3-Hydroxanthranilate 3-Hydroxanthranilic acid 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-Hydroxyantranilate 3-Hydroxyantranilic acid 3-OH-anthranilate 3-OH-anthranilic acid 3-OHAA 3-Oxyanthranilate 3-Oxyanthranilic acid
Chemical Formula:	C7H7NO3
Weight:	Average: 153.1354 Monoisotopic: 153.042593095
InChI Key:	WJXSWCUQABXPFS-UHFFFAOYSA-N
InChI:	InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
CAS number:	548-93-6
IUPAC Name:	2-amino-3-hydroxybenzoic acid
Traditional IUPAC Name:	3-hydroxyanthranilic acid
SMILES:	NC1=C(O)C=CC=C1C(O)=O
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.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Benzene and substituted derivatives
Sub Class	Benzoic acids and derivatives
Direct Parent	Hydroxybenzoic acid derivatives
Alternative Parents	Aminobenzoic acids Benzoic acids o-Aminophenols Aniline and substituted anilines Benzoyl derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Vinylogous amides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Hydrocarbon derivatives Organic oxides Organooxygen compounds Organopnictogen compounds Primary amines
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 Framework	Aromatic homomonocyclic compounds
External Descriptors	monohydroxybenzoic acid (CHEBI:15793 ) aminobenzoic acid (CHEBI:15793 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 10.5 g/L ALOGPS logP 0.81 ALOGPS logP 1.15 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.94 ChemAxon pKa (Strongest Basic) 4.82 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 83.55 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 40 m³·mol⁻¹ ChemAxon Polarizability 14.18 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2 3-Hydroxyanthranilic acid + 4 Oxygen <> Cinnavalininate +2 Superoxide anion +2 Hydrogen peroxide +2 Hydrogen ion
SMPDB Pathways:	Tryptophan metabolism PW000815
KEGG Pathways:	1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 Tryptophan metabolism ec00380
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0zfv-0945000000-e3389ab25b7133eb184d View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-0zfu-1955000000-fd51cc45bf09750e2b48 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0zfv-0945000000-e3389ab25b7133eb184d View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0zfu-1955000000-fd51cc45bf09750e2b48 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0zfv-0934000000-11e2b38a36cb364bcaf3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0006-0920000000-a57d310e9ca51aefd0c1 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0zg0-2900000000-f4f0b5c84821e81f2eea View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00e9-6390000000-71ab4928435b01bf5b59 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-000i-0900000000-2313e347dd8659099393 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-001i-9400000000-4e342fdebc8145b606a1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-001i-9000000000-ee5255b437ae762be1f9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-qTof , Positive splash10-000t-2900000000-a68dc7ca20e1f9595f15 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0zfr-0900000000-ced0a738a11057bc94e4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0a4i-0900000000-cded3154e50c6169c670 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0a4i-0900000000-9c388fc3035f19e3f156 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0a4i-1900000000-9dbb06a7728aab173e0f View in MoNA LC-MS/MS LC-MS/MS Spectrum - , negative splash10-0a4i-0900000000-19cfe2cda31cf7284669 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-000i-0900000000-02ae2bd70b54df77aca5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-000i-0900000000-56e21a4ececd5541a7d8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-052r-0900000000-e3015612b3d263fabaa9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-0a5i-3900000000-670c7d91a38e852d8e4c View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-000i-5900000000-36b3a876d06807eb22a3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Positive splash10-052r-0900000000-e3015612b3d263fabaa9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0a5i-3900000000-670c7d91a38e852d8e4c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900000000-56e21a4ececd5541a7d8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-000i-0900000000-02ae2bd70b54df77aca5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-053i-3900000000-a410eeec27727c997dc7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0900000000-84ae4ad8e91e8e4b6a6b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0k9i-1900000000-6695f66ad1f45898b8b6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0pxr-9300000000-43045627b8c856bf07d2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0pb9-0900000000-810a4a12ecb151ecb516 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-1900000000-9f194909a88a4ac248b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-8900000000-608d595690e7902b6195 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. Pubmed: 1244085 De Antoni A, Rubaltelli FF, Costa C, Allegri G: Effect of phototherapy on the urinary excretion of tryptophan metabolites in neonatal hyperbilirubinemia. Acta Vitaminol Enzymol. 1975;29(1-6):145-50. Pubmed: 1244083 Hegedus ZL, Frank HA, Altschule MD, Nayak U: Human plasma lipofuscin melanins formed from tryptophan metabolites. Arch Int Physiol Biochim. 1986 Dec;94(5):339-48. Pubmed: 2440410 Herve C, Beyne P, Jamault H, Delacoux E: Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):157-61. Pubmed: 8634758 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Lopez AS, Alegre E, LeMaoult J, Carosella E, Gonzalez A: Regulatory role of tryptophan degradation pathway in HLA-G expression by human monocyte-derived dendritic cells. Mol Immunol. 2006 Jul;43(14):2151-60. Epub 2006 Feb 21. Pubmed: 16490253 Teulings FA, Lems PH, Portengen H, Henkelman MS, Blonk DI: The action of 3-hydroxyanthranilic acid and other tryptophan metabolites on stimulated human lymphocytes. Acta Vitaminol Enzymol. 1975;29(1-6):113-6. Pubmed: 1244079 Teulings FA, Mulder-Kooy GE, Peters HA, Fokkens W, Van Der Werf-Messing B: The excretion of 3-hydroxyanthranilic acid in patients with bladder and kidney carcinoma. Acta Vitaminol Enzymol. 1975;29(1-6):108-12. Pubmed: 1244078 Werner ER, Lutz H, Fuchs D, Hausen A, Huber C, Niederwieser D, Pfleiderer W, Reibnegger G, Troppmair J, Wachter H: Identification of 3-hydroxyanthranilic acid in mixed lymphocyte cultures. Biol Chem Hoppe Seyler. 1985 Jan;366(1):99-102. Pubmed: 3159398 Yeh JK, Brown RR: Effects of vitamin B-6 deficiency and tryptophan loading on urinary excretion of tryptophan metabolites in mammals. J Nutr. 1977 Feb;107(2):261-71. Pubmed: 833687
Synthesis Reference:	Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 15793 HMDB ID HMDB01476 Pubchem Compound ID 86 Kegg ID C00632 ChemSpider ID 84 Wikipedia ID 3-hydroxyanthranilic_acid BioCyc ID 3-HYDROXY-ANTHRANILATE EcoCyc ID 3-HYDROXY-ANTHRANILATE Ligand Expo 3HA

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