Sedoheptulose 7-phosphate (YMDB00752)

Identification

YMDB ID

YMDB00752

Name

Sedoheptulose 7-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Sedoheptulose 7-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Sedoheptulose 7-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Sedoheptulose 7-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote). In yeast, sedoheptulose 7-phosphate is involved in the metabolic pathway called the riboneogenesis pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

7-(dihydrogen phosphate) sedoheptulose
altro-heptulose 7-phosphate
D-altro-Heptulose 7-phosphate
D-Sedoheptulose 7-phosphate
D-Sedoheptulose 7-phosphic acid
d-sedoheptulose-7-p
D-sedoheptulose-7-phosphate
heptulose-7-phosphate
Sedoheptulose 7-phosphate
Sedoheptulose-7-p
sedoheptulose-7-phosphate
Altro-heptulose 7-phosphoric acid
D-Altro-heptulose 7-phosphoric acid
D-Sedoheptulose 7-phosphoric acid
Sedoheptulose 7-phosphoric acid

CAS number

2646-35-7

Weight

Average: 290.1618
Monoisotopic: 290.040283212

InChI Key

JDTUMPKOJBQPKX-GBNDHIKLSA-N

InChI

InChI=1S/C7H15O10P/c8-1-3(9)5(11)7(13)6(12)4(10)2-17-18(14,15)16/h4-8,10-13H,1-2H2,(H2,14,15,16)/t4-,5-,6-,7+/m1/s1

IUPAC Name

{[(2R,3R,4R,5S)-2,3,4,5,7-pentahydroxy-6-oxoheptyl]oxy}phosphonic acid

Traditional IUPAC Name

sedoheptulose-7-phosphate

Chemical Formula

C₇H₁₅O₁₀P

SMILES

OCC(=O)[C@@H](O)[C@H](O)[C@H](O)[C@H](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

Substituents

Heptose monosaccharide
Monosaccharide 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
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoheptose phosphate (CHEBI:15721 )
sedoheptulose derivative (CHEBI:15721 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	25.1 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	184.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	54.4 m³·mol⁻¹	ChemAxon
Polarizability	23.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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

Organoleptic Properties

Not Available

SMPDB Pathways

Riboneogenesis	PW002511
xylitol degradation	PW002433

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05gj-7950000000-ec16725906be0353fe5c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-3590000000-beb43376b75330818dfd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9710000000-da3e7cbb0d13e0a9852f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-bf280537f2111db2fa33	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-9730000000-95d5d8154dd52ae89762	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-013bf5e975401d875686	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ed1b1f0cc92369220eba	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
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
Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
Pitkanen, J. P., Rintala, E., Aristidou, A., Ruohonen, L., Penttila, M. (2005). "Xylose chemostat isolates of Saccharomyces cerevisiae show altered metabolite and enzyme levels compared with xylose, glucose, and ethanol metabolism of the original strain." Appl Microbiol Biotechnol 67:827-837.15630585
Banki, K., Halladay, D., Perl, A. (1994). "Cloning and expression of the human gene for transaldolase. A novel highly repetitive element constitutes an integral part of the coding sequence." J Biol Chem 269:2847-2851.8300619

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15721
HMDB ID	HMDB01068
Pubchem Compound ID	46878379
Kegg ID	C00281
ChemSpider ID	24784759
FOODB ID	Not Available
Wikipedia	Sedoheptulose_7-phosphate
BioCyc ID	D-SEDOHEPTULOSE-7-P

Enzymes

Protein Details

1. Transketolase 2

General function:: Involved in catalytic activity
Specific function:: Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:: TKL2
Uniprot ID:: P33315
Molecular weight:: 75028.79688

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.

Protein Details

2. Transaldolase NQM1

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: NQM1
Uniprot ID:: P53228
Molecular weight:: 37253.30078

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.

Protein Details

3. Transketolase 1

General function:: Involved in catalytic activity
Specific function:: Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate
Gene Name:: TKL1
Uniprot ID:: P23254
Molecular weight:: 73805.0

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-ribose 5-phosphate + D-xylulose 5-phosphate.

Protein Details

4. Transaldolase

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway
Gene Name:: TAL1
Uniprot ID:: P15019
Molecular weight:: 37036.0

Reactions

Sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate → D-erythrose 4-phosphate + D-fructose 6-phosphate.

Structure for #<Compound:0xa7165754>

Enzymes

Reactions

Reactions

Reactions

Reactions