Identification
YMDB IDYMDB00753
Namesedoheptulose 1,7-bisphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSedoheptulose 1,7-bisphosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Sedoheptulose 1,7-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). sedoheptulose 1,7-bisphosphate can be converted into D-sedoheptulose 7-phosphate; which is mediated by the enzyme sedoheptulose 1,7-bisphosphatase. In yeast, sedoheptulose 1,7-bisphosphate is involved in the metabolic pathway called the riboneogenesis pathway.
Structure
Thumb
Synonyms
  • altro-Heptulose 1,7-biphosphate
  • D-altro-Heptulose 1,7-biphosphate
  • D-Sedoheptulose 1,7-bisphosphate
  • Sedoheptulose 1,7-bisphosphate
  • altro-Heptulose 1,7-biphosphoric acid
  • Sedoheptulose 1,7-bisphosphoric acid
  • D-altro-Heptulose 1,7-biphosphoric acid
  • D-Sedoheptulose 1,7-bisphosphoric acid
  • altro Heptulose 1,7-Bisphosphate
  • D-Sedoheptulose 1,7-diphosphate
  • D-altro-Heptulose 1,7-bisphosphate
CAS number815-91-8
WeightAverage: 370.1417
Monoisotopic: 370.006613622
InChI KeyOKHXOUGRECCASI-SHUUEZRQSA-N
InChIInChI=1S/C7H16O13P2/c8-3(1-19-21(13,14)15)5(10)7(12)6(11)4(9)2-20-22(16,17)18/h3,5-8,10-12H,1-2H2,(H2,13,14,15)(H2,16,17,18)/t3-,5-,6-,7-/m1/s1
IUPAC Name{[(3S,4R,5R,6R)-3,4,5,6-tetrahydroxy-2-oxo-7-(phosphonooxy)heptyl]oxy}phosphonic acid
Traditional IUPAC Namesedoheptulose 1,7-bisphosphate
Chemical FormulaC7H16O13P2
SMILESO[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)COP(O)(O)=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
  • Heptose monosaccharide
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-1.5ALOGPS
logP-4.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area231.51 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.27 m³·mol⁻¹ChemAxon
Polarizability28.03 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
RiboneogenesisPW002511 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
sedoheptulose 1,7-bisphosphate + waterD-Sedoheptulose 7-phosphate + phosphate
KEGG Reactions
Adenosine triphosphate + D-Sedoheptulose 7-phosphatehydron + sedoheptulose 1,7-bisphosphate + ADP
sedoheptulose 1,7-bisphosphateD-Erythrose 4-phosphate + Dihydroxyacetone phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9812000000-89e1f3c83fa5fb790408JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0077-6924026000-72068c6e0e0bd236a3c3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1449000000-bdc810a6f38e6acfa267JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-4911000000-75c70e044d501546322dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000e-9800000000-37ddc2ef1990d4acc39bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00os-6922000000-b6f948267750931218e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0e8dfa987ccac2c50817JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f5325e6f93a21599e5cfJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kuznetsova, E., Xu, L., Singer, A., Brown, G., Dong, A., Flick, R., Cui, H., Cuff, M., Joachimiak, A., Savchenko, A., Yakunin, A. F. (2010). "Structure and activity of the metal-independent fructose-1,6-bisphosphatase YK23 from Saccharomyces cerevisiae." J Biol Chem 285:21049-21059.20427268
  • Clasquin, M. F., Melamud, E., Singer, A., Gooding, J. R., Xu, X., Dong, A., Cui, H., Campagna, S. R., Savchenko, A., Yakunin, A. F., Rabinowitz, J. D., Caudy, A. A. (2011). "Riboneogenesis in yeast." Cell 145:969-980.21663798
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17969
HMDB IDHMDB0060274
Pubchem Compound ID164735
Kegg IDC00447
ChemSpider ID144412
FOODB IDNot Available
Wikipedia IDSedoheptulose-bisphosphatase
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the aldol condensation of dihydroxyacetone phosphate (DHAP or glycerone-phosphate) with glyceraldehyde 3- phosphate (G3P) to form fructose 1,6-bisphosphate (FBP) in gluconeogenesis and the reverse reaction in glycolysis
Gene Name:
FBA1
Uniprot ID:
P14540
Molecular weight:
39620.5
Reactions
D-fructose 1,6-bisphosphate → glycerone phosphate + D-glyceraldehyde 3-phosphate.
General function:
ribosome biogenesis
Specific function:
Sedoheptulose 1,7-bisphosphatase involved in riboneogenesis. Dephosphorylates sedoheptulose 1,7-bisphosphate (SBP), which is converted via the non-oxidative pentose phosphate pathway to ribose-5-phosphate. Has a fructose 1,6-bisphosphatase activity in vitro, but this is probably not biologically relevant, since deletion does not affect fructose 1,6-biphosphate (FBP) levels.
Gene Name:
SHB17
Uniprot ID:
P36136
Molecular weight:
31021.71
Reactions