Record Information
Version2.0
Creation Date2012-05-31 14:06:42 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04151
Identification
Name:Salicin
DescriptionSalicin is an alcoholic beta-glucoside. Salicin is closely related in chemical make-up to aspirin. Salicin can be used as a sugar substrate by E. coli and can be imported into the cytoplasm as salicin-6-phosphate through the ascF gene product.
Structure
Thumb
Synonyms:
  • 2-(hydroxymethyl)-phenyl-β-D-glucopyranoside
  • 2-(Hydroxymethyl)-phenyl-b-D-glucopyranoside
  • 2-(Hydroxymethyl)-phenyl-beta-D-glucopyranoside
  • 2-(Hydroxymethyl)-phenyl-β-D-glucopyranoside
  • 2-(Hydroxymethyl)phenyl hexopyranoside
  • D(-)-Salicin
  • D-Salicin
  • Delta-Salicin
  • Salicin
  • Salicine
  • Salicoside
  • Salicyl alcohol glucoside
  • Saligenin b-D-glucopyranoside
  • Saligenin b-delta-glucopyranoside
  • Saligenin b-δ-glucopyranoside
  • Saligenin beta-D-glucopyranoside
  • Saligenin beta-delta-glucopyranoside
  • Saligenin β-D-glucopyranoside
  • Saligenin β-δ-glucopyranoside
  • Saligenin-b-D-glucopyranoside
  • Saligenin-b-delta-glucopyranoside
  • Saligenin-b-δ-glucopyranoside
  • Saligenin-beta-D-glucopyranoside
  • Saligenin-beta-delta-glucopyranoside
  • Saligenin-β-D-glucopyranoside
  • Saligenin-β-δ-glucopyranoside
  • δ-Salicin
Chemical Formula:C13H18O7
Weight:Average: 286.2778
Monoisotopic: 286.10525293
InChI Key:NGFMICBWJRZIBI-UJPOAAIJSA-N
InChI: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
CAS number:138-52-3
IUPAC Name:(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Traditional IUPAC Name:salicin
SMILES:OC[C@H]1O[C@@H](OC2=C(CO)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
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
Physical Properties
State:Solid
Charge:0
Melting point:207 °C
Experimental Properties:
PropertyValueSource
Water Solubility:40 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-1.22 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP-1.1ALOGPS
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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
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
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Julkunen-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)
External Links:
ResourceLink
CHEBI ID17814
HMDB IDHMDB03546
Pubchem Compound ID439503
Kegg IDC01451
ChemSpider ID388601
WikipediaSalicin
BioCyc IDCPD-1142
EcoCyc IDCPD-1142
Ligand ExpoSA0

Enzymes

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
Acts as both a kinase and a phosphatase on BglG
Gene Name:
bglF
Uniprot ID:
P08722
Molecular weight:
66482
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in arbutin, cellobiose, and salicin transport
Gene Name:
ascF
Uniprot ID:
P24241
Molecular weight:
51025
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:
crr
Uniprot ID:
P69783
Molecular weight:
18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.

Transporters

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
Acts as both a kinase and a phosphatase on BglG
Gene Name:
bglF
Uniprot ID:
P08722
Molecular weight:
66482
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in arbutin, cellobiose, and salicin transport
Gene Name:
ascF
Uniprot ID:
P24241
Molecular weight:
51025
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.