Record Information
Version2.0
Creation Date2012-07-30 14:54:54 -0600
Update Date2015-06-03 17:20:52 -0600
Secondary Accession Numbers
  • ECMDB21200
Identification
Name:D-Glycero-D-manno-heptose 1-phosphate
DescriptionD-glycero-D-manno-heptose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. D-Glycero-D-manno-heptose 1-phosphate is involved in the biosynthesis of the lipopolysaccharide core precursor ADP-L-glycero-D-manno-heptose. (PMID 10629197)
Structure
Thumb
Synonyms:
  • 1-O-Phosphono-D-glycero-Dmanno-heptopyranose
  • D-glycero-b-D-manno-Heptose 1-phosphate
  • D-glycero-b-D-manno-Heptose 1-phosphoric acid
  • D-Glycero-beta-D-manno-Heptose 1-phosphate
  • D-glycero-beta-D-manno-Heptose 1-phosphoric acid
  • D-Glycero-D-manno-Heptose 1-phosphate
  • D-glycero-D-manno-Heptose 1-phosphoric acid
  • D-Glycero-Dmanno-heptopyranose 1-(dihydrogen phosphate)
  • D-glycero-dmanno-Heptopyranose 1-(dihydrogen phosphoric acid)
  • D-glycero-β-D-manno-Heptose 1-phosphate
  • D-glycero-β-D-manno-Heptose 1-phosphoric acid
Chemical Formula:C7H13O10P
Weight:Average: 288.1459
Monoisotopic: 288.024633148
InChI Key:KMEJCSKJXSBBAN-NNPWBXLPSA-L
InChI:InChI=1S/C7H15O10P/c8-1-2(9)6-4(11)3(10)5(12)7(16-6)17-18(13,14)15/h2-12H,1H2,(H2,13,14,15)/p-2/t2-,3+,4+,5+,6-,7?/m1/s1
CAS number:Not Available
IUPAC Name:(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl phosphate
Traditional IUPAC Name:(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl phosphate
SMILES:[H][C@@](O)(CO)[C@@]1([H])OC([H])(OP([O-])([O-])=O)[C@@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility89.7 g/LALOGPS
logP-2.3ALOGPS
logP-3.7ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.8 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.52 m³·mol⁻¹ChemAxon
Polarizability22.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 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, Positivesplash10-000i-1290000000-aaa95c90e2c25ab1eb7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-5390000000-c7c93f6013718fe9653fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08or-9300000000-fd0ccf7f1c5b0851e0afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-5490000000-8f63d602921aa5a4ad22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06y9-9240000000-6456aee3da9be9939619View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9200000000-e9fe10c075b6dd73eedbView in MoNA
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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28137
HMDB IDNot Available
Pubchem Compound ID46878581
Kegg IDC07838
ChemSpider ID26331785
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in phosphatase activity
Specific function:
Converts the D-glycero-beta-D-manno-heptose 1,7- bisphosphate intermediate into D-glycero-beta-D-manno-heptose 1- phosphate by removing the phosphate group at the C-7 position
Gene Name:
gmhB
Uniprot ID:
P63228
Molecular weight:
21294
Reactions
D-glycero-beta-D-manno-heptose 1,7-bisphosphate + H(2)O = D-glycero-beta-D-manno-heptose 1-phosphate + phosphate.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the ADP transfer to D-glycero-D-manno-heptose 1-phosphate, yielding ADP-D,D-heptose
Gene Name:
hldE
Uniprot ID:
P76658
Molecular weight:
51050
Reactions
ATP + D-glycero-beta-D-manno-heptose 7-phosphate = ADP + D-glycero-beta-D-manno-heptose 1,7-bisphosphate.
ATP + D-glycero-beta-D-manno-heptose 1-phosphate = diphosphate + ADP-D-glycero-beta-D-manno-heptose.