Salicin (ECMDB04151) (M2MDB000640)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)Transporters (2)XML
Proteins (121)
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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:
Protein N(pi)-phospho-L-histidine + Salicin <> Protein histidine + Salicin 6-phosphate
Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acid
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
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 SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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

Protein Details
1. PTS system beta-glucoside-specific EIIBCA component
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.
Protein Details
2. PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component
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.
Protein Details
3. Glucose-specific phosphotransferase enzyme IIA component
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

Protein Details
1. PTS system beta-glucoside-specific EIIBCA component
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.
Protein Details
2. PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component
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.