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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-6970000000-4a3fc41bdfdcae61270aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-001i-1111149000-413e4462b838237eb990View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0920000000-dd9147181f57af043933View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-5f01886cdb3b1b83482dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a6r-6900000000-60990058ed2008115d3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-b0ab03332dc31197e24dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-1eff788038412eafc6e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0920000000-e1a9ed30eb900b2d13f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0930000000-53b80e6d9343986fce22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0479000000-e3d1fa41cebd0db517ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0469000000-7bd2e826ca0d8c4e246bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a9a3323c5bcb7537be88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0079-4990000000-21e7ed9f578486c41d30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00dl-6900000000-abca856686e2a48f338bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d01a7791218632604919View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2ce515c6b24230bee91dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0910000000-8157b002a15ff7712810View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a59-0900000000-08e0bc3883a8879210c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-7900000000-60f3f4e5be9e785ee227View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r9-0970000000-300143a83a460b0b8de6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-d56d227c3ed2911b275eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-da1f6546fa4860684208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0790000000-705ce708dcc235d02e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-3940000000-1b35dca166815881ea11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-45d5d35d6bc2783638e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-3920000000-e8aa896614066fd2844cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2940000000-2eba30eb86decafa5403View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
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