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D-Glycero-D-manno-heptose 1,7-bisphosphate (M2MDB001607)

Record Information
Version2.0
Creation Date2012-07-30 14:54:54 -0600
Update Date2015-06-03 17:20:51 -0600
Secondary Accession Numbers
  • ECMDB21199
Identification
Name:D-Glycero-D-manno-heptose 1,7-bisphosphate
DescriptionD-glycero-D-manno-heptose 1,7-bisphosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (5R)-5-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]-1-O-phosphono-D-lyxopyranose
  • D-β-D-heptose-1,7-bisphosphate
  • D-β-D-heptose-1,7-bisphosphoric acid
  • D-glycero-β-D-manno-heptose 1,7-PP
  • D-b-D-Heptose-1,7-bisphosphate
  • D-b-D-Heptose-1,7-bisphosphoric acid
  • D-beta-D-Heptose-1,7-bisphosphate
  • D-beta-D-Heptose-1,7-bisphosphoric acid
  • D-Glycero-β-D-manno-heptose 1,7-PP
  • D-glycero-b-D-manno-Heptose 1,7-bisphosphate
  • D-glycero-b-D-manno-Heptose 1,7-bisphosphoric acid
  • D-glycero-b-D-manno-Heptose 1,7-PP
  • D-Glycero-beta-D-manno-Heptose 1,7-bisphosphate
  • D-glycero-beta-D-manno-Heptose 1,7-bisphosphoric acid
  • D-Glycero-beta-D-manno-heptose 1,7-PP
  • D-Glycero-D-manno-Heptose 1,7-bisphosphate
  • D-glycero-D-manno-Heptose 1,7-bisphosphoric acid
  • D-glycero-β-D-manno-Heptose 1,7-bisphosphate
  • D-glycero-β-D-manno-Heptose 1,7-bisphosphoric acid
  • D-glycero-β-D-manno-Heptose 1,7-PP
  • D-β-D-Heptose-1,7-bisphosphate
  • D-β-D-Heptose-1,7-bisphosphoric acid
Chemical Formula:C7H16O13P2
Weight:Average: 370.1417
Monoisotopic: 370.006613622
InChI Key:LMTGTTLGDUACSJ-NNPWBXLPSA-N
InChI:InChI=1S/C7H16O13P2/c8-2(1-18-21(12,13)14)6-4(10)3(9)5(11)7(19-6)20-22(15,16)17/h2-11H,1H2,(H2,12,13,14)(H2,15,16,17)/t2-,3+,4+,5+,6-,7?/m1/s1
CAS number:Not Available
IUPAC Name:{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]oxan-2-yl]oxyphosphonic acid
SMILES:[H][C@@](O)(COP(O)(O)=O)[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
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility19 g/LALOGPS
logP-1.6ALOGPS
logP-3.8ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area223.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.63 m³·mol⁻¹ChemAxon
Polarizability28.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
D-Glycero-D-manno-heptose 1,7-bisphosphate + Water <> D-Glycero-D-manno-heptose 1-phosphate + Phosphate
Adenosine triphosphate + D-Glycero-D-manno-heptose 7-phosphate > ADP + D-Glycero-D-manno-heptose 1,7-bisphosphate + Hydrogen ion
Adenosine triphosphate + D-glycero-beta-D-manno-Heptose 7-phosphate + D-glycero-beta-D-manno-heptose 7-phosphate <> ADP + D-Glycero-D-manno-heptose 1,7-bisphosphate
D-Glycero-D-manno-heptose 1,7-bisphosphate + Water > D-<i>glycero</i>-&beta;-D-<i>manno</i>-heptose 1-phosphate + Phosphate
D-Glycero-D-manno-heptose 1,7-bisphosphate + Water > D-glycero-beta-D-manno-heptose 1-phosphate + Inorganic phosphate
D-Glycero-D-manno-heptose 1,7-bisphosphate + Water > D-glycero-beta-D-manno-heptose 1-phosphate + Phosphate
SMPDB Pathways:
ADP-L-glycero-Beta-D-manno-heptose biosynthesisPW002095 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • ADP-L-glycero-β-D-manno-heptose biosynthesis PWY0-1241
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_25) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2169000000-47e8c9bff5e77136fbaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-7394000000-b55ec34b4058b89845d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9510000000-41aa1835d82b6d49ac89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-9476000000-9f38782861c88b901852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-6b36f31dfb655ca666d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ba84b37e8d788b88ac7dView in MoNA
References
References:
  • 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 ID4188
HMDB IDNot Available
Pubchem Compound ID443223
Kegg IDC11472
ChemSpider ID391487
Wikipedia IDNot Available
BioCyc IDD-BETA-D-HEPTOSE-17-DIPHOSPHATE
EcoCyc IDD-BETA-D-HEPTOSE-17-DIPHOSPHATE

Enzymes

Protein Details
1. D,D-heptose 1,7-bisphosphate phosphatase
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.
Protein Details
2. Bifunctional protein hldE
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.