Record Information
Version2.0
Creation Date2012-08-09 09:25:10 -0600
Update Date2015-06-03 17:21:40 -0600
Secondary Accession Numbers
  • ECMDB21504
Identification
Name:6-Phospho-beta-D-glucosyl-(1,4)-D-glucose
Description6-phospho-beta-D-glucosyl-(1,4)-D-glucose is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates.
Structure
Thumb
Synonyms:
  • 4-O-(6-O-phosphono-b-D-Glucopyranosyl)-b-D-glucopyranose
  • 4-O-(6-O-Phosphono-beta-D-glucopyranosyl)-beta-D-glucopyranose
  • 4-O-(6-O-phosphono-β-D-Glucopyranosyl)-β-D-glucopyranose
  • 6-O-phosphono-b-D-Glucopyranosyl-(1Right4)-b-D-glucopyranose
  • 6-O-Phosphono-beta-D-glucopyranosyl-(1right4)-beta-D-glucopyranose
  • 6-O-phosphono-β-D-Glucopyranosyl-(1Right4)-β-D-glucopyranose
  • 6-phospho-b-D-Glucosyl-(1,4)-D-glucose
  • 6-Phospho-beta-D-glucosyl-(1,4)-D-glucose
  • 6-phospho-β-D-Glucosyl-(1,4)-D-glucose
  • Cellobiose 6-phosphate
  • Cellobiose 6-phosphoric acid
Chemical Formula:C12H23O14P
Weight:Average: 422.2764
Monoisotopic: 422.082541956
InChI Key:ITPHOIFCAFNCLL-QRZGKKJRSA-N
InChI:InChI=1S/C12H23O14P/c13-1-3-10(7(16)8(17)11(19)24-3)26-12-9(18)6(15)5(14)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxyphosphonic acid
SMILES:[H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentDisaccharide phosphates
Alternative Parents
Substituents
  • Disaccharide phosphate
  • Glycosyl compound
  • O-glycosyl compound
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • 6-phospho-beta-D-glucosyl-(1->4)-D-glucose (CHEBI:2233 )
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility40.7 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.21 m³·mol⁻¹ChemAxon
Polarizability35.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08n9-0902500000-b67f737a4a61476245c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1900000000-6b9e43fb6a7ba155cce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-1900000000-23a1f23a5ac78392918eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-9634800000-7dc62f0a531f731360bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-89ae5f03d5f8e22417d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-d86f9a65f1c247ebc70bView in MoNA
References
References:
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID2233
HMDB IDNot Available
Pubchem Compound ID440376
Kegg IDC04534
ChemSpider ID389331
Wikipedia IDNot Available
BioCyc IDNot Available

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:
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.
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 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.