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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:03 UTC
HMDB IDHMDB15471
Secondary Accession NumbersNone
Metabolite Identification
Common NameSalsalate
DescriptionSalsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo. Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body. The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.
Structure
Thumb
Synonyms
ValueSource
2-Carboxyphenyl salicylateChEBI
DisalcidChEBI
Disalicylic acidChEBI
DisalicylsaeureChEBI
O-SalicylcylsalicylsaeureChEBI
O-Salicylsalicylic acidChEBI
Salicylic acid bimolecular esterChEBI
Salicyloxysalicylic acidChEBI
Salicyloylsalicylic acidChEBI
Salicylsalicylic acidChEBI
SalsalatoChEBI
SalsalatumChEBI
SasapyrinChEBI
SasapyrinumChEBI
2-Carboxyphenyl salicylic acidGenerator
DisalicylateGenerator
O-SalicylsalicylateGenerator
Salicylate bimolecular esterGenerator
SalicyloxysalicylateGenerator
SalicyloylsalicylateGenerator
SalicylsalicylateGenerator
Chemical FormulaC14H10O5
Average Molecular Weight258.2262
Monoisotopic Molecular Weight258.05282343
IUPAC Name2-(2-hydroxybenzoyloxy)benzoic acid
Traditional Namesalina
CAS Registry Number552-94-3
SMILES
OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)
InChI KeyInChIKey=WVYADZUPLLSGPU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Salicylic acid or derivatives
  • Phenol ester
  • Benzoate ester
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenol
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.46e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 mg/mLALOGPS
logP3.44ALOGPS
logP3.64ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.1 m3·mol-1ChemAxon
Polarizability24.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Salsalate Action PathwaySMP00707Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01399
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01399
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01399
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4977
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB15471
Metagene LinkHMDB15471
METLIN IDNot Available
PubChem Compound5161
PDB IDNot Available
ChEBI ID355532
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Stichtenoth DO, Zeidler H, Frolich JC: [New non-steroidal anti-rheumatic drugs: selective inhibitors of inducible cyclooxygenase]. Med Klin (Munich). 1998 Jul 15;93(7):407-15. [9711054 ]
  2. Schaefer MG, Plowman BK, Morreale AP, Egan M: Interaction of rofecoxib and celecoxib with warfarin. Am J Health Syst Pharm. 2003 Jul 1;60(13):1319-23. [12901032 ]
  3. Motsko SP, Rascati KL, Busti AJ, Wilson JP, Barner JC, Lawson KA, Worchel J: Temporal relationship between use of NSAIDs, including selective COX-2 inhibitors, and cardiovascular risk. Drug Saf. 2006;29(7):621-32. [16808554 ]
  4. Josephs MD, Cheng G, Ksontini R, Moldawer LL, Hocking MP: Products of cyclooxygenase-2 catalysis regulate postoperative bowel motility. J Surg Res. 1999 Sep;86(1):50-4. [10452868 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Stevenson DD: Aspirin and NSAID sensitivity. Immunol Allergy Clin North Am. 2004 Aug;24(3):491-505, vii. [15242723 ]
  2. Schmidt A, Hescheler J, Offermanns S, Spicher K, Hinsch KD, Klinz FJ, Codina J, Birnbaumer L, Gausepohl H, Frank R, et al.: Involvement of pertussis toxin-sensitive G-proteins in the hormonal inhibition of dihydropyridine-sensitive Ca2+ currents in an insulin-secreting cell line (RINm5F). J Biol Chem. 1991 Sep 25;266(27):18025-33. [1680855 ]
  3. Josephs MD, Cheng G, Ksontini R, Moldawer LL, Hocking MP: Products of cyclooxygenase-2 catalysis regulate postoperative bowel motility. J Surg Res. 1999 Sep;86(1):50-4. [10452868 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]