Showing metabocard for Salicin (BMDB0003546)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:12 UTC
Update Date2020-05-05 18:40:27 UTC
BMDB IDBMDB0003546
Secondary Accession Numbers
  • BMDB03546
Metabolite Identification
Common NameSalicin
DescriptionSalicin, also known as salicoside, 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. Salicin exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Salicin.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2(Hydroxymethyl)phenyl-beta-D-glucopyranosideChEBI
2-(Hydroxymethyl)phenyl-beta-D-glucopyranosideChEBI
2-(Hydroxymethyl)phenyl-O-beta-D-glucopyranosideChEBI
D-(-)-SalicinChEBI
O-(Hydroxymethyl)phenyl beta-D-glucopyranosideChEBI
SalicosideChEBI
Salicyl alcohol glucosideChEBI
Saligenin beta-D-glucopyranosideChEBI
2(Hydroxymethyl)phenyl-b-D-glucopyranosideGenerator
2(Hydroxymethyl)phenyl-β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-b-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-O-b-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl-O-β-D-glucopyranosideGenerator
O-(Hydroxymethyl)phenyl b-D-glucopyranosideGenerator
O-(Hydroxymethyl)phenyl β-D-glucopyranosideGenerator
Saligenin b-D-glucopyranosideGenerator
Saligenin β-D-glucopyranosideGenerator
2-(Hydroxymethyl)phenyl hexopyranosideHMDB
D-SalicinHMDB
delta-SalicinHMDB
SalicineHMDB
Saligenin beta-delta-glucopyranosideHMDB
Saligenin-b-D-glucopyranosideHMDB
Saligenin-beta-D-glucopyranosideHMDB
Saligenin-beta-delta-glucopyranosideHMDB
Chemical FormulaC13H18O7
Average Molecular Weight286.2778
Monoisotopic Molecular Weight286.10525293
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Traditional Namesalicin
CAS Registry Number138-52-3
SMILES
OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChI KeyNGFMICBWJRZIBI-UJPOAAIJSA-N
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
  • O-glycosyl compound
  • Phenoxy compound
  • Benzyl alcohol
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40 mg/mL at 25 °CNot Available
LogP-1.22HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67 m³·mol⁻¹ChemAxon
Polarizability27.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003546
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023194
KNApSAcK IDC00002672
Chemspider ID388601
KEGG Compound IDC01451
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSalicin
METLIN ID6948
PubChem Compound439503
PDB IDNot Available
ChEBI ID17814
References
Synthesis ReferenceJulkunen-Tiitto, Riitta; Meier, Beat. The enzymic decomposition of salicin and its derivatives obtained from Salicaceae species. Journal of Natural Products (1992), 55(9), 1204-12.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available