Sedoheptulose 1,7-bisphosphate (ECMDB20192) (M2MDB001038)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (664)
Record Information
Version2.0
Creation Date2012-05-31 14:32:23 -0600
Update Date2015-10-15 16:14:32 -0600
Secondary Accession Numbers
  • ECMDB20192
Identification
Name:Sedoheptulose 1,7-bisphosphate
DescriptionSedoheptulose 1,7-bisphosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. Sedoheptulose-1,7-bisphosphate is invovled in the photosynthetic Calvin cycle. Sedoheptulose-1,7-bisphosphatase (SBPase) is an enzyme unique to photosynthetic organisms and has a key role in regulating the photosynthetic Calvin cycle through which nearly all carbon enters the biosphere. (PMID 9758762)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • D-Altro-Heptulose 1,7-biphosphate
  • D-altro-Heptulose 1,7-biphosphoric acid
  • D-Sedoheptulose 1,7-bisphosphate
  • D-Sedoheptulose 1,7-bisphosphoric acid
  • D-Sedoheptulose-1,7-bisphosphate
  • D-Sedoheptulose-1,7-bisphosphoric acid
  • D-Sedoheptulose-1,7-diphosphate
  • D-Sedoheptulose-1,7-diphosphoric acid
  • D-Sedoheptulose-1,7-P2
  • D-sedoheptulose-1,7-P2
  • D-SEDOHEPTULOSE-1-7-P2
  • SBP
  • Sedoheptulose 1,7-bisphosphate
  • Sedoheptulose 1,7-bisphosphoric acid
Chemical Formula:C7H16O13P2
Weight:Average: 370.1417
Monoisotopic: 370.006613622
InChI Key:OKHXOUGRECCASI-SHUUEZRQSA-N
InChI:InChI=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
CAS number:815-91-8
IUPAC Name:{[3,4,5,6-tetrahydroxy-2-oxo-7-(phosphonooxy)heptyl]oxy}phosphonic acid
Traditional IUPAC Name:[3,4,5,6-tetrahydroxy-2-oxo-7-(phosphonooxy)heptyl]oxyphosphonic acid
SMILES:O[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 DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability27.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Sedoheptulose 1,7-bisphosphate <> Dihydroxyacetone phosphate + D-Erythrose 4-phosphate
Adenosine triphosphate + D-Sedoheptulose 7-phosphate > ADP + Hydrogen ion + Sedoheptulose 1,7-bisphosphate
Dihydroxyacetone phosphate + D-Erythrose 4-phosphate < Sedoheptulose 1,7-bisphosphate
SMPDB Pathways:Not Available
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1449000000-3c02a67a86debad115daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-4911000000-3da0cb05dba80c23029aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9810000000-ccfb662079550b0c93f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00os-6922000000-fc350c1e09e5af190393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-6a31d2e20b15c2f291deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3501cbf5d338c1280144View in MoNA
References
References:
  • Dunford, R. P., Catley, M. A., Raines, C. A., Lloyd, J. C., Dyer, T. A. (1998). "Purification of active chloroplast sedoheptulose-1,7-bisphosphatase expressed in Escherichia coli." Protein Expr Purif 14:139-145. Pubmed: 9758762
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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 ID17969
HMDB IDNot Available
Pubchem Compound ID1193
Kegg IDC00447
ChemSpider ID1156
Wikipedia IDSedoheptulose-bisphosphatase
BioCyc IDD-SEDOHEPTULOSE-1-7-P2
EcoCyc IDD-SEDOHEPTULOSE-1-7-P2

Enzymes

Protein Details
1. 6-phosphofructokinase isozyme 1
General function:
Involved in ATP binding
Specific function:
ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
Gene Name:
pfkA
Uniprot ID:
P0A796
Molecular weight:
34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate.
Protein Details
2. Fructose-bisphosphate aldolase class 1
General function:
Involved in catalytic activity
Specific function:
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:
fbaB
Uniprot ID:
P0A991
Molecular weight:
38109
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.
Protein Details
3. Fructose-bisphosphate aldolase class 2
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:
fbaA
Uniprot ID:
P0AB71
Molecular weight:
39147
Reactions
D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate.