β-D-glucose 1-phosphate (ECMDB24239) (M2MDB006356)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (5)Transporters (1)XML
Proteins (5)
Record Information
Version2.0
Creation Date2015-09-08 17:50:21 -0600
Update Date2015-09-14 16:46:08 -0600
Secondary Accession Numbers
  • ECMDB24239
Identification
Name:β-D-glucose 1-phosphate
DescriptionBeta-D-glucose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Trehalose phosphorylase from Thermoanaerobacter sp. is a glycoside hydrolase family 65 enzyme which catalyzes the reversible breakdown of trehalose [D-glucopyranosyl-alpha(1,1)alpha-D-glucopyranose] to beta-D-glucose 1-phosphate and D-glucose. (PMID 20383018) SgrS is an Hfq-binding small RNA that is induced under glucose phosphate stress in Escherichia coli. (PMID 18650387)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • β-D-glucose 1-phosphoric acid
Chemical Formula:C5H9O9P
Weight:Average: 244.093
Monoisotopic: 243.999516028
InChI Key:VPFDELVVUOEHIT-OGZQUKKDSA-L
InChI:InChI=1S/C5H11O9P/c6-1-2(7)4(9)13-5(3(1)8)14-15(10,11)12/h1-9H,(H2,10,11,12)/p-2/t1-,2-,3+,4+,5-/m1/s1
CAS number:Not Available
IUPAC Name:(2R,3S,4R,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl phosphate
Traditional IUPAC Name:(2R,3S,4R,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl phosphate
SMILES:O[C@H]1O[C@H](OP([O-])([O-])=O)[C@@H](O)[C@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility100 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area162.57 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.62 m³·mol⁻¹ChemAxon
Polarizability18.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
β-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > UDP-Glucose + Pyrophosphate
beta-D-Glucose 6-phosphate > β-D-glucose 1-phosphate
D-Glucose + [PTS enzyme I]-Nπ-phospho-L-histidine > β-D-glucose 1-phosphate + [PTS enzyme I]-L-histidine
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
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 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, Positivesplash10-0002-0290000000-d5a1bcfb11133f2fb980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-1490000000-7cbb5bf73ce1ac403ab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-9600000000-3a09785f254a23c3cba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-5390000000-b6d7fcd2483b1eb03fc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-9470000000-11559d4bc8fe72d99628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9100000000-7edbb5bbaf49b85b4c76View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. UTP--glucose-1-phosphate uridylyltransferase_
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase activity
Specific function:
May play a role in stationary phase survival
Gene Name:
galU
Uniprot ID:
P0AEP3
Molecular weight:
32942
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
Protein Details
2. 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
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.
Protein Details
4. PTS system glucose-specific EIICB 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 glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
5. Putative beta-phosphoglucomutase
General function:
Involved in beta-phosphoglucomutase activity
Specific function:
Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
Gene Name:
ycjU
Uniprot ID:
P77366
Molecular weight:
23565
Reactions
Beta-D-glucose 1-phosphate = beta-D-glucose 6-phosphate.

Transporters

Protein Details
1. PTS system glucose-specific EIICB 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 glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.