| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:25 -0700 |
| HMDB ID |
HMDB00840 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Salicyluric acid |
| Description |
Salicyluric acid is an aryl glycine conjugate formed by the body to eliminate excess salicylates, including aspirin. Aspirin is rapidly hydrolysed to salicylic acid which is further metabolized to various compounds, including salicyluric acid (SU) as well as various acyl and phenolic glucuronides, and hydroxylated metabolites. SU is the major metabolite of SA excreted in urine and it is present in the urine of people who have not taken salicylate drugs, although it has no anti-inflammatory effects in humans or in animals. More salicyluric acid (SU) is excreted in the urine of vegetarians than in non-vegetarians, primarily because fruits and vegetables are important sources of dietary salicylates. However, significantly less (10-15X) SU is excreted by vegetarians than individuals taking low-dose aspirin (PMID: 12944546  ). The induction of the salicyluric acid formation is one of the saturable pathways of salicylate elimination. The formation of the methyl ester of salicyluric acid is observed during the quantitation of salicyluric acid and other salicylate metabolites in urine by high-pressure liquid chromatography. This methyl ester formation causes artificially low values for salicyluric acid and high values for salicylic acid. (PMID: 6101164 , 6857178 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- ((2-hydroxybenzoyl)amino)acetic acid
- (2-Hydroxybenzoyl)glycine
- 2-Hydroxybenzoylaminoacetate
- 2-Hydroxybenzoylaminoacetic acid
- 2-Hydroxybenzoylglycine
- 2-Hydroxyhippurate
- 2-Hydroxyhippuric acid
- N-(2-Hydroxybenzoyl)-glycine
- N-O-Hydroxybenzoylglycine
- N-Salicyloylglycine
- O-Hydroxy-Hippurate
- O-Hydroxy-Hippuric acid
- O-Hydroxyhippurate
- O-Hydroxyhippuric acid
- Ortho-Hydroxyhippurate
- Ortho-Hydroxyhippuric acid
- Salicylglycine
- Salicyloylglycine
- Salicylurate
- Salicyluric acid
- [(2-Hydroxybenzoyl)amino]acetate
- [(2-Hydroxybenzoyl)amino]acetic acid
|
| Chemical Formula |
C9H9NO4 |
| Average Molecular Weight |
195.1721 |
| Monoisotopic Molecular Weight |
195.053157781 |
| IUPAC Name |
2-[(2-hydroxyphenyl)formamido]acetic acid |
| Traditional IUPAC Name |
salicyluric acid |
| CAS Registry Number |
487-54-7 |
| SMILES |
OC(=O)CNC(=O)C1=CC=CC=C1O |
| InChI Identifier |
InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13) |
| InChI Key |
ONJSZLXSECQROL-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Alpha Amino Acids and Derivatives
- Aromatic Homomonocyclic Compounds
- N-acyl-amino acid(ChEBI)
- hydroxy-amino acid(ChEBI)
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| Substituents |
- Benzamide
- Benzoyl
- Carboxamide Group
- Carboxylic Acid
- Hippurate
- Phenol
- Phenol Derivative
- Secondary Carboxylic Acid Amide
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| Direct Parent |
Acyl Glycines |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
168 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
0.95 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
|
| Spectra |
|---|
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| Biological Properties |
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| Cellular Locations |
Not Available
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| Biofluid Locations |
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
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|
| Blood |
Detected and Quantified |
|
1.000 +/- 0.015 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.7 (0.3-1.8) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Vegetarians
|
| Urine |
Detected and Quantified |
|
0.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.23 (0.01-0.8) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Non-vegetarians
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| Urine |
Detected and Quantified |
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11.0 (0.3-28) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Individuals on low dose aspirin
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| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Expected and not Quantified |
|
Not Applicable |
Not Available |
Not Available |
Consuming polyphenols described by Phenol-Explorer entry 928 |
Not Available |
| Urine |
Expected and not Quantified |
|
Not Applicable |
Not Available |
Not Available |
Consuming polyphenols described by Phenol-Explorer entry 928 |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
After ingested soluble aspirin BP 600mg...
|
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| Abnormal Concentrations |
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|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
928 |
| FoodDB ID |
FDB010505 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
9835 |
| KEGG Compound ID |
C07588 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00840 |
| Metagene Link |
HMDB00840 |
| METLIN ID |
617 |
| PubChem Compound |
10253 |
| PDB ID |
Not Available |
| ChEBI ID |
9008 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Pirker R, Huck CW, Popp M, Bonn GK: Simultaneous determination of gentisic, salicyluric and salicylic acid in human plasma using solid-phase extraction, liquid chromatography and electrospray ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Oct 5;809(2):257-64.
Pubmed: 15315774
- Lares-Asseff I, Juarez-Olguin H, Flores-Perez J, Guille-Perez A, Vargas A: Pharmacokinetics and metabolic rates of acetyl salicylic acid and its metabolites in an Otomi ethnic group of Mexico. Biol Pharm Bull. 2004 May;27(5):706-9.
Pubmed: 15133250
- Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes] Yakugaku Zasshi. 1996 Aug;116(8):630-8.
Pubmed: 8831264
- Farid NA, Born GS, Kessler WV, Shaw SM, Lange WE: Improved colorimetric determination of salicylic acid and its metabolites in urine. Clin Chem. 1975 Jul;21(8):1167-8.
Pubmed: 1137922
- Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3.
Pubmed: 7074905
- Kershaw RA, Mays DC, Bianchine JR, Gerber N: Disposition of aspirin and its metabolites in the semen of man. J Clin Pharmacol. 1987 Apr;27(4):304-9.
Pubmed: 3680588
- Lawrence JR, Peter R, Baxter GJ, Robson J, Graham AB, Paterson JR: Urinary excretion of salicyluric and salicylic acids by non-vegetarians, vegetarians, and patients taking low dose aspirin. J Clin Pathol. 2003 Sep;56(9):651-3.
Pubmed: 12944546
- Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4.
Pubmed: 7356541
- Arancibia JA, Olivieri AC, Escandar GM: First- and second-order multivariate calibration applied to biological samples: determination of anti-inflammatories in serum and urine. Anal Bioanal Chem. 2002 Oct;374(3):451-9. Epub 2002 Sep 11.
Pubmed: 12373394
- Baxter GJ, Lawrence JR, Graham AB, Wiles D, Paterson JR: Identification and determination of salicylic acid and salicyluric acid in urine of people not taking salicylate drugs. Ann Clin Biochem. 2002 Jan;39(Pt 1):50-5.
Pubmed: 11853189
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