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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:28:36 UTC
Update Date2019-01-11 19:17:39 UTC
HMDB IDHMDB0003546
Secondary Accession Numbers
  • HMDB03546
Metabolite Identification
Common NameSalicin
DescriptionSalicin is an alcoholic β-glycoside that contains D-glucose. Salicin is an anti-inflammatory agent that is produced from willow bark. Salicin is closely related in chemical make-up to aspirin and has a very similar action in the human body. When consumed by humans, Salicin is metabolized into salicylic acid.
Structure
Data?1547234259
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
Disposition

Source:

Biological location:

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
Water Solubility24.9 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-016s-0931000000-d7cfab7dda5ba5b8cb8dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-6970000000-4a3fc41bdfdcae61270aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-001i-1111149000-413e4462b838237eb990JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0920000000-dd9147181f57af043933JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0900000000-5f01886cdb3b1b83482dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a6r-6900000000-60990058ed2008115d3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-b0ab03332dc31197e24dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0aor-0970000000-1eff788038412eafc6e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0920000000-e1a9ed30eb900b2d13f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0930000000-53b80e6d9343986fce22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0479000000-e3d1fa41cebd0db517ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0469000000-7bd2e826ca0d8c4e246bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r9-0970000000-300143a83a460b0b8de6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-d56d227c3ed2911b275eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-da1f6546fa4860684208JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0790000000-705ce708dcc235d02e31JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-3940000000-1b35dca166815881ea11JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-45d5d35d6bc2783638e4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
General References
  1. Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [PubMed:8831264 ]
  2. Mahdi JG, Mahdi AJ, Mahdi AJ, Bowen ID: The historical analysis of aspirin discovery, its relation to the willow tree and antiproliferative and anticancer potential. Cell Prolif. 2006 Apr;39(2):147-55. [PubMed:16542349 ]
  3. Sadatsune T, Moreno G: [Contribution to the study of the haemolytic streptococci isolated from dogs (author's transl)]. Arq Inst Biol (Sao Paulo). 1975;42:257-64. [PubMed:1236057 ]
  4. Brenner DJ, Hickman-Brenner FW, Holmes B, Hawkey PM, Penner JL, Grimont PA, O'Hara CM: Replacement of NCTC 4175, the current type strain of Proteus vulgaris, with ATCC 29905. Request for an opinion. Int J Syst Bacteriol. 1995 Oct;45(4):870-1. [PubMed:7547312 ]