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Salicin 6-phosphate (M2MDB001037)

Record Information
Version2.0
Creation Date2012-05-31 14:32:20 -0600
Update Date2015-06-03 17:19:30 -0600
Secondary Accession Numbers
  • ECMDB20191
Identification
Name:Salicin 6-phosphate
DescriptionSalicin 6-phosphate is a sugar phosphate, derived from salicin which is an alcoholic beta-glucoside.. It is generated when salicin is transported from the periplasmic space into the cytoplasm by the CelT protein The reaction is as follows: phosphoenolpyruvate + salicin[periplasmic space] ¡ú salicin-6-phosphate[cytosol] + pyruvate. Salicin 6-phosphate is s substrate for CelF. CelF has been shown to hydrolyze a variety of P-beta-glucosides, including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P and methyl-beta-glucoside-6P. (PMID:10572139)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • Salicin 6-phosphoric acid
  • Salicin-6-p
  • Salicin-6P
  • [3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonate
  • [3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonic acid
Chemical Formula:C13H19O10P
Weight:Average: 366.2577
Monoisotopic: 366.07158334
InChI Key:FSJKOMDYZYBBLV-UJPOAAIJSA-N
InChI:InChI=1S/C13H19O10P/c14-5-7-3-1-2-4-8(7)22-13-12(17)11(16)10(15)9(23-13)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H2,18,19,20)/t9-,10-,11+,12-,13-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:salicin-6P
SMILES:[H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=CC=C2CO)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide phosphate
  • Phenoxy compound
  • Benzyl alcohol
  • Phenol ether
  • Monoalkyl phosphate
  • Monocyclic benzene moiety
  • Benzenoid
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.9 g/LALOGPS
logP-1.4ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.87 m³·mol⁻¹ChemAxon
Polarizability32.21 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
Salicin 6-phosphate + Water <> Salicyl alcohol + beta-D-Glucose 6-phosphate
Salicin 6-phosphate + Water > Glucose 6-phosphate + salicyl alcohol
Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acid
Salicin 6-phosphate + Water > β-D-glucose 1-phosphate + Salicyl alcohol
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r1-0926000000-799ba792f13c42272f4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0910000000-93f476e72bd7886ae558View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1900000000-47f1449e4952346dc0e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01dj-7918000000-ddde1165dbe50bbc4229View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-8c2ab404ab39a797f491View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-5f603aa181ea5c52ad3cView in MoNA
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID9003
HMDB IDNot Available
Pubchem Compound ID440938
Kegg IDC06188
ChemSpider ID389767
Wikipedia IDNot Available
BioCyc IDCPD-1181
EcoCyc IDCPD-1181
Ligand ExpoP53

Enzymes

Protein Details
1. 6-phospho-beta-glucosidase BglB
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin and arbutin
Gene Name:
bglB
Uniprot ID:
P11988
Molecular weight:
53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
2. 6-phospho-beta-glucosidase AscB
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin, cellobiose, and probably arbutin
Gene Name:
ascB
Uniprot ID:
P24240
Molecular weight:
53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
3. 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
4. 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.
Protein Details
5. 6-phospho-beta-glucosidase BglA
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
Gene Name:
bglA
Uniprot ID:
Q46829
Molecular weight:
55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.

Transporters

Protein Details
1. 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.