Record Information
Version2.0
Creation Date2012-05-31 14:34:03 -0600
Update Date2015-06-03 17:19:34 -0600
Secondary Accession Numbers
  • ECMDB20225
Identification
Name:2-Deoxy-D-glucose 6-phosphate
Description2-deoxyglucose-6-phosphate is a sugar phosphate. It is a substrate for 2-deoxyglucose-6-phosphatase (EC 3.1.3.68) which is an enzyme that catalyzes the chemical reaction 2-deoxy-D-glucose 6-phosphate + H2O <-> 2-deoxy-D-glucose + phosphate The two substrates of this enzyme are 2-deoxy-D-glucose 6-phosphate and H2O, whereas its two products are 2-deoxy-D-glucose and phosphate. 2-deoxyglucose-6-phosphatase or YniC is a sugar phosphatase belonging to the superfamily of haloacid dehalogenase (HAD)-like hydrolases.
Structure
Thumb
Synonyms:
  • (2R,3S,4R)-3,4,6-trihydroxyoxan-2-ylmethyl dihydrogen phosphate
  • (2R,3S,4R)-3,4,6-Trihydroxyoxan-2-ylmethyl dihydrogen phosphoric acid
  • 2-Deoxy-6-O-phospho-D-glucopyranose
  • 2-Deoxy-D-glucose 6-phosphoric acid
Chemical Formula:C6H13O8P
Weight:Average: 244.1364
Monoisotopic: 244.034803904
InChI Key:UQJFZAAGZAYVKZ-CERMHHMHSA-N
InChI:InChI=1S/C6H13O8P/c7-3-1-5(8)14-4(6(3)9)2-13-15(10,11)12/h3-9H,1-2H2,(H2,10,11,12)/t3-,4-,5?,6+/m1/s1
CAS number:56-73-5
IUPAC Name:{[(2R,3S,4R)-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:2-deoxy-D-glucose 6-phosphate
SMILES:[H]C1(O)C[C@@]([H])(O)[C@]([H])(O)[C@@]([H])(COP(O)(O)=O)O1
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
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • 1,2-diol
  • Secondary alcohol
  • Hemiacetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP-2.1ALOGPS
logP-2.2ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.29 m³·mol⁻¹ChemAxon
Polarizability20.19 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
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, Positivesplash10-0002-1490000000-ac1179ec6e3eca85815dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-7950000000-6a0eebecf40c496b107eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9400000000-1455867dd900b9f85bbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-8590000000-3f51d04d5e63084b70a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-ba9e421c655898ad66c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6f07756648adddacbad1View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16043
HMDB IDNot Available
Pubchem Compound ID440992
Kegg IDC06369
ChemSpider ID389817
Wikipedia IDNot Available
BioCyc ID2-DEOXY-D-GLUCOSE-6-PHOSPHATE
EcoCyc ID2-DEOXY-D-GLUCOSE-6-PHOSPHATE

Enzymes

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
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 mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
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.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Not Available
Specific function:
Not Available
Gene Name:
yniC
Uniprot ID:
P77247
Molecular weight:
Not Available

Transporters

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303