Salsalate (CHEM016869)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:45:59 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016869
Identification
Common NameSalsalate
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
SasapyrineChEBI
SasapyrinumChEBI
2-Carboxyphenyl salicylic acidGenerator
DisalicylateGenerator
O-SalicylsalicylateGenerator
Salicylate bimolecular esterGenerator
SalicyloxysalicylateGenerator
SalicyloylsalicylateGenerator
SalicylsalicylateGenerator
Salsalic acidGenerator
SalflexHMDB
SalsitabHMDB
SaloxiumHMDB
ArcylateHMDB
ArgesicHMDB
Upsher-smith brand OF salicylsalicylic acidHMDB
mono-GesicHMDB
Salicyl salicylateHMDB
Benzoic acid, 2-hydroxy-, 2-carboxyphenyl esterHMDB
Chemical FormulaC14H10O5
Average Molecular Mass258.226 g/mol
Monoisotopic Mass258.053 g/mol
CAS Registry Number552-94-3
IUPAC Name2-(2-hydroxybenzoyloxy)benzoic acid
Traditional Namesalina
SMILESOC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O
InChI IdentifierInChI=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 KeyWVYADZUPLLSGPU-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • O-hydroxybenzoic acid ester
  • Benzoate ester
  • Salicylic acid or derivatives
  • Phenol ester
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.1 m³·mol⁻¹ChemAxon
Polarizability24.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-08ef63493442bd429803Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-1902000000-a534dd5fbce0addc2689Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0290000000-f4cf330edbdce3dcb9d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2790000000-d10c0ecafec2d5a9b8daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9500000000-1c6bcbed20e1fdde65d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0090000000-18be47c801d297da7fd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2190000000-e79b3cc4f48105579dfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-4b93814ccff2c3ff93c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-4731b64bd7f33c92a35fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-dccaf7be8cfaf84a3394Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9100000000-5cf64c11c5e0756d69baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9150000000-cdfb845a922b2d914e6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-eb933123d7cea37777a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-8ba532e581907de890bdSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01399
HMDB IDHMDB0015471
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSalsalate
Chemspider ID4977
ChEBI ID9014
PubChem Compound ID5161
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19747808
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20613460
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20876710
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21289240
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21519323
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21617098
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21764223
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21903749
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21938543
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22357964
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22388922
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22517326
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22782506
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22784842
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23370525
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23680037
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23801715
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23817699
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23817718
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23825542
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23871515
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23948064
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24130358
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217