Arbutin 6-phosphate (ECMDB20117) (M2MDB000965)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (9)Transporters (2)XML
Proteins (240)
Record Information
Version2.0
Creation Date2012-05-31 14:28:22 -0600
Update Date2015-06-03 17:19:20 -0600
Secondary Accession Numbers
  • ECMDB20117
Identification
Name:Arbutin 6-phosphate
DescriptionArbutin 6-phosphate is a member of the chemical class known as Hexose phosphates. These are phospho-monosaccharides in which the sugar unit is a hexose.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Arbutin 6-phosphate
  • Arbutin 6-phosphoric acid
  • Arbutin-6-p
  • Arbutin-6P
Chemical Formula:C12H17O10P
Weight:Average: 352.2311
Monoisotopic: 352.055933276
InChI Key:FBHYCDOVYMVLEN-RMPHRYRLSA-N
InChI:InChI=1S/C12H17O10P/c13-6-1-3-7(4-2-6)21-12-11(16)10(15)9(14)8(22-12)5-20-23(17,18)19/h1-4,8-16H,5H2,(H2,17,18,19)/t8-,9-,10+,11-,12-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:arbutin-6P
SMILES:[H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=C(O)C=C2)[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
  • 4-alkoxyphenol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • 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 Solubility10.3 g/LALOGPS
logP-0.86ALOGPS
logP-1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.04 m³·mol⁻¹ChemAxon
Polarizability30.4 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Arbutin > Arbutin 6-phosphate + Pyruvic acid
Arbutin 6-phosphate + Water > Glucose 6-phosphate + Hydroquinone
Protein N(pi)-phospho-L-histidine + Arbutin <> Protein histidine + Arbutin 6-phosphate
Arbutin 6-phosphate + Water <> Hydroquinone + beta-D-Glucose 6-phosphate
Arbutin + Phosphoenolpyruvic acid > Arbutin 6-phosphate + Pyruvic acid
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0936000000-d4046102e0d59c4ea2a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910000000-27010452832f40545c01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-c7958319cfe2d210662fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zi0-7908000000-5099b4bde6db23537a0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9400000000-139a4894686681b1ce6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-9c758149a11024fb7f29View in MoNA
MSMass Spectrum (Electron Ionization)Not 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
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 ID2807
HMDB IDNot Available
Pubchem Compound ID440937
Kegg IDC06187
ChemSpider ID389766
Wikipedia IDNot Available
BioCyc IDCPD-1162
EcoCyc IDCPD-1162

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. Phosphoenolpyruvate-protein phosphotransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein Details
3. 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
4. 6-phospho-beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:
chbF
Uniprot ID:
P17411
Molecular weight:
50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
5. 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
6. 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
7. 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
8. 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.
Protein Details
9. Phosphocarrier protein HPr
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

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.