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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 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
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