ChemFOnt: Showing chemical card for Salsalate (CFc000009741)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:58 UTC

Chemfont ID

CFc000009741

Molecule Identification

Common Name

Salsalate

Definition

Salsalate 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Carboxyphenyl salicylate	ChEBI
Disalcid	ChEBI
Disalicylic acid	ChEBI
Disalicylsaeure	ChEBI
O-Salicylcylsalicylsaeure	ChEBI
O-Salicylsalicylic acid	ChEBI
Salicylic acid bimolecular ester	ChEBI
Salicyloxysalicylic acid	ChEBI
Salicyloylsalicylic acid	ChEBI
Salicylsalicylic acid	ChEBI
Salsalato	ChEBI
Salsalatum	ChEBI
Sasapyrin	ChEBI
Sasapyrine	ChEBI
Sasapyrinum	ChEBI
2-Carboxyphenyl salicylic acid	Generator
Disalicylate	Generator
O-Salicylsalicylate	Generator
Salicylate bimolecular ester	Generator
Salicyloxysalicylate	Generator
Salicyloylsalicylate	Generator
Salicylsalicylate	Generator
Salsalic acid	Generator
Salflex	HMDB
Salsitab	HMDB
Saloxium	HMDB
Arcylate	HMDB
Argesic	HMDB
Upsher-smith brand OF salicylsalicylic acid	HMDB
mono-Gesic	HMDB
Salicyl salicylate	HMDB
Benzoic acid, 2-hydroxy-, 2-carboxyphenyl ester	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Molecular Weight

258.2262

Monoisotopic Molecular Weight

258.05282343

IUPAC Name

2-(2-hydroxybenzoyloxy)benzoic acid

Traditional Name

salina

CAS Registry Number

552-94-3

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 Key

WVYADZUPLLSGPU-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).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:9014 )
salicylates (CHEBI:9014 )
benzoate ester (CHEBI:9014 )
benzoic acids (CHEBI:9014 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015471)
Membrane (HMDB: HMDB0015471)

Source

Exogenous

Exogenous (HMDB: HMDB0015471)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Salsalate Action Pathway (PathBank: SMP0000707)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.64	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.1 m³·mol⁻¹	ChemAxon
Polarizability	24.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015471

DrugBank ID

DB01399

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salsalate

METLIN ID

Not Available

PubChem Compound

5161

PDB ID

Not Available

ChEBI ID

9014

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Salsalate (CFc000009741)

MOL for CFc000009741 (Salsalate)

3D MOL for CFc000009741 (Salsalate)

3D SDF for CFc000009741 (Salsalate)

3D-SDF for CFc000009741 (Salsalate)

PDB for CFc000009741 (Salsalate)

3D PDB for CFc000009741 (Salsalate)

SMILES for CFc000009741 (Salsalate)

INCHI for CFc000009741 (Salsalate)

Structure for CFc000009741 (Salsalate)

3D Structure for CFc000009741 (Salsalate)