Human Metabolome Database Version 3.5

Showing metabocard for Salicyluric acid (HMDB00840)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:17 -0600
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 Link_out). 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 Link_out, 6857178 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. ((2-hydroxybenzoyl)amino)acetic acid
  2. (2-Hydroxybenzoyl)glycine
  3. 2-Hydroxybenzoylaminoacetate
  4. 2-Hydroxybenzoylaminoacetic acid
  5. 2-Hydroxybenzoylglycine
  6. 2-Hydroxyhippurate
  7. 2-Hydroxyhippuric acid
  8. N-(2-Hydroxybenzoyl)-glycine
  9. N-O-Hydroxybenzoylglycine
  10. N-Salicyloylglycine
  11. O-Hydroxy-Hippurate
  12. O-Hydroxy-Hippuric acid
  13. O-Hydroxyhippurate
  14. O-Hydroxyhippuric acid
  15. Ortho-Hydroxyhippurate
  16. Ortho-Hydroxyhippuric acid
  17. Salicylglycine
  18. Salicyloylglycine
  19. Salicylurate
  20. Salicyluric acid
  21. [(2-Hydroxybenzoyl)amino]acetate
  22. [(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)
Substituents
  • Benzamide
  • Benzoyl
  • Carboxamide Group
  • Carboxylic Acid
  • Hippurate
  • Phenol
  • Phenol Derivative
  • Secondary Carboxylic Acid Amide
Direct Parent Acyl Glycines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
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)
Predicted Properties
Property Value Source
Water Solubility 4.04 g/L ALOGPS
LogP 0.51 ALOGPS
LogP 0.87 ChemAxon
LogS -1.68 ALOGPS
pKa (strongest acidic) 3.27 ChemAxon
pKa (strongest basic) -2 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 86.63 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 48.1 ChemAxon
Polarizability 18.4 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.000 +/- 0.015 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.7 (0.3-1.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.5 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.23 (0.01-0.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
11.0 (0.3-28) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 928
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 928
  • Not Applicable
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID 928 Link_out
FoodDB ID FDB010505
KNApSAcK ID Not Available
Chemspider ID 9835 Link_out
KEGG Compound ID C07588 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00840 Link_out
Metagene Link HMDB00840 Link_out
METLIN ID 617 Link_out
PubChem Compound 10253 Link_out
PDB ID Not Available
ChEBI ID 9008 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. Day RO, Dromgoole SH, Furst DE, Hignite C, Paulus HE: Formation of methyl ester of salicyluric acid during quantitation of salicyluric acid in urine by high-pressure liquid chromatography. J Pharm Sci. 1981 Sep;70(9):1090-2. Pubmed: 6101164 Link_out
  12. Olsson B: Decreasing serum salicylate concentrations during long-term administration of acetylsalicylic acid in healthy volunteers. Discussion of possible clinical implications. Scand J Rheumatol. 1983;12(2):81-4. Pubmed: 6857178 Link_out

Enzymes
Name: Glycine N-acyltransferase
Reactions: Not Available
Gene Name: GLYAT
Uniprot ID: Q6IB77 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine N-acyltransferase-like protein 1
Reactions: Not Available
Gene Name: GLYATL1
Uniprot ID: Q969I3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine N-acyltransferase-like protein 2
Reactions: Not Available
Gene Name: GLYATL2
Uniprot ID: Q8WU03 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine N-acyltransferase-like protein 3
Reactions: Not Available
Gene Name: GLYATL3
Uniprot ID: Q5SZD4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA