Salicylic acid 2-beta-D-glucoside (CHEM026091)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:46:57 UTC
Update Date2016-11-09 01:18:12 UTC
Accession NumberCHEM026091
Identification
Common NameSalicylic acid 2-beta-D-glucoside
ClassSmall Molecule
DescriptionA benzoate resulting from the removal of a proton from the carboxylic acid group of 2-(beta-D-glucopyranosyloxy)benzoic acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(beta-D-Glucosyloxy)benzoateChEBI
2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}benzoateChEBI
Salicylate 2-O-beta-D-glucosideChEBI
2-(b-D-Glucosyloxy)benzoateGenerator
2-(b-D-Glucosyloxy)benzoic acidGenerator
2-(beta-D-Glucosyloxy)benzoic acidGenerator
2-(Β-D-glucosyloxy)benzoateGenerator
2-(Β-D-glucosyloxy)benzoic acidGenerator
2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}benzoic acidGenerator
Salicylate 2-O-b-D-glucosideGenerator
Salicylate 2-O-β-D-glucosideGenerator
Salicylic acid 2-O-b-D-glucosideGenerator
Salicylic acid 2-O-beta-D-glucosideGenerator
Salicylic acid 2-O-β-D-glucosideGenerator
2-(b-D-Glucopyranosyloxy)benzoateGenerator
2-(b-D-Glucopyranosyloxy)benzoic acidGenerator
2-(beta-D-Glucopyranosyloxy)benzoic acidGenerator
2-(Β-D-glucopyranosyloxy)benzoateGenerator
2-(Β-D-glucopyranosyloxy)benzoic acidGenerator
Salicylic acid 2-O-β-D-glucosideMetaCyc
Salicylic acid 2-β-D-glucosideMetaCyc
2-O-β-glucopyranosylsalicylic acidMetaCyc
SAGMetaCyc
2-Hydroxybenzoic acid 2-O-β-D-glucosideMetaCyc
Salicylate 2-O-β-D-glucosideGenerator
Salicylate 2-b-D-glucosideGenerator
Salicylate 2-beta-D-glucosideGenerator
Salicylate 2-β-D-glucosideGenerator
Salicylic acid 2-b-D-glucosideGenerator
Salicylic acid 2-β-D-glucosideGenerator
Chemical FormulaC13H15O8
Average Molecular Mass299.256 g/mol
Monoisotopic Mass299.077 g/mol
CAS Registry NumberNot Available
IUPAC Name2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate
Traditional Name2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate
SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC=CC=C2C([O-])=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI IdentifierInChI=1S/C13H16O8/c14-5-8-9(15)10(16)11(17)13(21-8)20-7-4-2-1-3-6(7)12(18)19/h1-4,8-11,13-17H,5H2,(H,18,19)/p-1/t8-,9-,10+,11-,13-/m1/s1
InChI KeyTZPBMNKOLMSJPF-BZNQNGANSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Sugar acid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility57.6 g/LALOGPS
logP-0.88ALOGPS
logP-0.94ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.51 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.28 m³·mol⁻¹ChemAxon
Polarizability27.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0229000000-37b6b991f9499a941f06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1391000000-9ddc89597fcf0d8d3c26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9710000000-14e39df57fcedbc427d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1290000000-0e0dad854a3cdade5126Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-6790000000-cc2126848fcb04409d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-854d4c7057f2aff14dddSpectrum
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 IDNot Available
HMDB IDHMDB0302794
FooDB IDFDB006279
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5448097
ChEBI ID145670
PubChem Compound IDNot Available
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=19117519
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=30294315
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=9662552