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
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:
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 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
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

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.
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.
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.
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

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.