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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:23 -0600
Update Date	2015-10-15 16:14:32 -0600
Secondary Accession Numbers	ECMDB20192
Identification
Name:	Sedoheptulose 1,7-bisphosphate
Description	Sedoheptulose 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xac3bcfe8> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharide phosphates
Alternative Parents	Heptoses Glycerone phosphates Monoalkyl phosphates Beta-hydroxy ketones Acyloins Alpha-hydroxy ketones Secondary alcohols Polyols Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.3 g/L ALOGPS logP -1.5 ALOGPS logP -4.1 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.01 ChemAxon pKa (Strongest Basic) -3.5 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 231.51 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 65.27 m³·mol⁻¹ ChemAxon Polarizability 27.83 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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:	sedoheptulose bisphosphate bypass PWY0-1517
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-1449000000-3c02a67a86debad115da View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-006w-4911000000-3da0cb05dba80c23029a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0005-9810000000-ccfb662079550b0c93f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00os-6922000000-fc350c1e09e5af190393 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9300000000-6a31d2e20b15c2f291de View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-3501cbf5d338c1280144 View 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
Links
External Links:	Resource Link CHEBI ID 17969 HMDB ID Not Available Pubchem Compound ID 1193 Kegg ID C00447 ChemSpider ID 1156 Wikipedia ID Sedoheptulose-bisphosphatase BioCyc ID D-SEDOHEPTULOSE-1-7-P2 EcoCyc ID D-SEDOHEPTULOSE-1-7-P2

Enzymes