| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:37 -0700 |
| HMDB ID |
HMDB01476 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D 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-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
|
| Chemical Formula |
C7H7NO3 |
| Average Molecular Weight |
153.1354 |
| Monoisotopic Molecular Weight |
153.042593095 |
| IUPAC Name |
2-amino-3-hydroxybenzoic acid |
| Traditional IUPAC Name |
3-hydroxyanthranilic acid |
| CAS Registry Number |
548-93-6 |
| SMILES |
NC1=C(O)C=CC=C1C(O)=O |
| InChI Identifier |
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) |
| InChI Key |
WJXSWCUQABXPFS-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Homomonocyclic Compounds |
| Class |
Benzoic Acid and Derivatives |
| Sub Class |
Hydroxybenzoic Acid Derivatives |
| Other Descriptors |
- Aminobenzoic Acid Derivatives
- Organic Compounds
- aminobenzoic acid(ChEBI)
- benzoic acids(ChEBI)
|
| Substituents |
- Aminophenol Derivative
- Aniline
- Benzoyl
- Carboxylic Acid
- Phenol
- Phenol Derivative
|
| Direct Parent |
Hydroxybenzoic Acid Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Tryptophan metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
- Bladder
- Lymphocyte
- Epidermis
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.079 (0.015-0.209) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.28 (0.46-5.19) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.01 (0.007-0.011) uM |
Adult (>18 years old) |
Both |
Stroke |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Stroke |
- Darlington LG, Mackay GM, Forrest CM, Stoy N, George C, Stone TW: Altered kynurenine metabolism correlates with infarct volume in stroke. Eur J Neurosci. 2007 Oct;26(8):2211-21. Epub 2007 Sep 24.
Pubmed: 17892481
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB03644  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB010582 |
| KNApSAcK ID |
C00007568  |
| Chemspider ID |
84  |
| KEGG Compound ID |
C00632  |
| BioCyc ID |
3-HYDROXY-ANTHRANILATE  |
| BiGG ID |
1485273  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB01476  |
| Metagene Link |
HMDB01476  |
| METLIN ID |
3275  |
| PubChem Compound |
86  |
| PDB ID |
3HA  |
| ChEBI ID |
15793  |
| References |
| Synthesis Reference |
Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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