P. aeruginosa Metabolome Database: 3-Hydroxyanthranilic acid (PAMDB000396)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000396

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

153.1354

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These 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

Substituents

Hydroxybenzoic acid
Aminobenzoic acid or derivatives
Aminobenzoic acid
Benzoic acid
Substituted aniline
Benzoyl
Aminophenol
Phenol
Aniline
Primary aromatic amine
Vinylogous amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
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 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40 m³·mol^-1	ChemAxon
Polarizability	14.18 Å³	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

Pathways:

1,4-Dichlorobenzene degradation pae00627
Microbial metabolism in diverse environments pae01120
Tryptophan metabolism pae00380

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)	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-MS	Not Available
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

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

3-Hydroxyanthranilic acid (PAMDB000396)

Structure for 3-Hydroxyanthranilic acid (PAMDB000396)