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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:29:17 UTC
HMDB IDHMDB00840
Secondary Accession NumbersNone
Metabolite Identification
Common NameSalicyluric acid
DescriptionSalicyluric 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
Thumb
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 FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name2-[(2-hydroxyphenyl)formamido]acetic acid
Traditional Namesalicyluric acid
CAS Registry Number487-54-7
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 KeyONJSZLXSECQROL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha 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 ParentAcyl Glycines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.95HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility4.04 g/LALOGPS
logP0.51ALOGPS
logP0.87ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.1ChemAxon
Polarizability18.4ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.000 +/- 0.015 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.7 (0.3-1.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.23 (0.01-0.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified11.0 (0.3-28) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 928
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 928
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID928
FoodDB IDFDB010505
KNApSAcK IDNot Available
Chemspider ID9835
KEGG Compound IDC07588
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00840
Metagene LinkHMDB00840
METLIN ID617
PubChem Compound10253
PDB IDNot Available
ChEBI ID9008
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. 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
  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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  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
  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
  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
  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

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3