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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015471
Secondary Accession Numbers
  • HMDB15471
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
Data?1582753300
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 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 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
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.25 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available151.271http://allccs.zhulab.cn/database/detail?ID=AllCCS00001385
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.68131661259
DarkChem[M-H]-157.20231661259
DeepCCS[M+H]+154.72430932474
DeepCCS[M-H]-152.32930932474
DeepCCS[M-2H]-185.8330932474
DeepCCS[M+Na]+160.76630932474
AllCCS[M+H]+157.132859911
AllCCS[M+H-H2O]+153.432859911
AllCCS[M+NH4]+160.732859911
AllCCS[M+Na]+161.732859911
AllCCS[M-H]-156.632859911
AllCCS[M+Na-2H]-156.032859911
AllCCS[M+HCOO]-155.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SalsalateOC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O3399.1Standard polar33892256
SalsalateOC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O2229.7Standard non polar33892256
SalsalateOC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O2240.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Salsalate,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O2215.3Semi standard non polar33892256
Salsalate,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1C(=O)O2322.6Semi standard non polar33892256
Salsalate,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O[Si](C)(C)C2336.6Semi standard non polar33892256
Salsalate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O2463.0Semi standard non polar33892256
Salsalate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1C(=O)O2582.9Semi standard non polar33892256
Salsalate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C2783.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Salsalate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-08ef63493442bd4298032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Salsalate GC-MS (2 TMS) - 70eV, Positivesplash10-0006-1902000000-a534dd5fbce0addc26892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Salsalate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 10V, Positive-QTOFsplash10-0a4l-0290000000-f4cf330edbdce3dcb9d92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 20V, Positive-QTOFsplash10-00dl-2790000000-d10c0ecafec2d5a9b8da2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 40V, Positive-QTOFsplash10-0uk9-9500000000-1c6bcbed20e1fdde65d52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 10V, Negative-QTOFsplash10-0bt9-0090000000-18be47c801d297da7fd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 20V, Negative-QTOFsplash10-03di-2190000000-e79b3cc4f48105579dfa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 40V, Negative-QTOFsplash10-0006-9300000000-4b93814ccff2c3ff93c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 10V, Positive-QTOFsplash10-00di-2900000000-4731b64bd7f33c92a35f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 20V, Positive-QTOFsplash10-00di-4900000000-dccaf7be8cfaf84a33942021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 40V, Positive-QTOFsplash10-0f6x-9100000000-5cf64c11c5e0756d69ba2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 10V, Negative-QTOFsplash10-052f-9150000000-cdfb845a922b2d914e6f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 20V, Negative-QTOFsplash10-0006-9000000000-eb933123d7cea37777a22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Salsalate 40V, Negative-QTOFsplash10-0006-9300000000-8ba532e581907de890bd2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01399 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01399 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01399
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4977
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSalsalate
METLIN IDNot Available
PubChem Compound5161
PDB IDNot Available
ChEBI ID9014
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10452868 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]