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D-Sedoheptulose 7-phosphate (YMDB00196)

Identification
YMDB IDYMDB00196
NameD-Sedoheptulose 7-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Sedoheptulose 7-phosphate, also known as D-sedoheptulose-7-p, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. D-Sedoheptulose 7-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Sedoheptulose 7-phosphate exists in all eukaryotes, ranging from yeast to humans. Within yeast, D-sedoheptulose 7-phosphate participates in a number of enzymatic reactions. In particular, D-sedoheptulose 7-phosphate can be biosynthesized from sedoheptulose 1,7-bisphosphate through its interaction with the enzyme sedoheptulose 1,7-bisphosphatase. In addition, D-sedoheptulose 7-phosphate and D-glyceraldehyde 3-phosphate can be converted into xylulose 5-phosphate and D-ribose 5-phosphate; which is mediated by the enzyme transketolase. In yeast, D-sedoheptulose 7-phosphate is involved in the metabolic pathway called the riboneogenesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 7-(dihydrogen phosphate) sedoheptulose
  • 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
  • D-Sedoheptulose 7-phosphoric acid
CAS number2646-35-7
WeightAverage: 290.1618
Monoisotopic: 290.040283212
InChI KeyCBIDVWSRUUODHL-QTSLKERKSA-N
InChIInChI=1S/C7H15O10P/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15/h3-6,8-12H,1-2H2,(H2,13,14,15)/t3-,4-,5-,6+,7?/m1/s1
IUPAC Name{[(2R,3S,4R,5S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxyphosphonic acid
Chemical FormulaC7H15O10P
SMILES[H]OC([H])([H])C1(O[H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility30.7 g/LALOGPS
logP-2.3ALOGPS
logP-3.5ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.2 m³·mol⁻¹ChemAxon
Polarizability23.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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
xylitol degradationPW002433 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Xylulose 5-phosphate + D-Ribose 5-phosphate → L-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
Xylulose 5-phosphate + D-Ribose 5-phosphate → D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate ↔ Xylulose 5-phosphate + D-Ribose 5-phosphate
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate → D-Erythrose 4-phosphate + β-D-fructofuranose 6-phosphate
sedoheptulose 1,7-bisphosphate + water → D-Sedoheptulose 7-phosphate + phosphate
KEGG Reactions
Adenosine triphosphate + D-Sedoheptulose 7-phosphate → hydron + sedoheptulose 1,7-bisphosphate + ADP
D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate ↔ D-Erythrose 4-phosphate + Fructose 6-phosphate
alpha-D-ribose 5-phosphate + Xylulose 5-phosphate ↔ D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05u2-9760000000-23220eac824fb093768eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-4300149000-6fba19ca6cd4460a42b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1490000000-d647c8b819afa525ac31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-6940000000-948baa6c0020169263a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-6900000000-f2ead32bc69a7827f273JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-009i-8790000000-18c40c04e91399064edeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b41f9c2b1d3edf3ab828JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-63453353080e28955933JSpectraViewer
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:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15721
HMDB IDHMDB01068
Pubchem Compound ID616
Kegg IDC00281
ChemSpider ID17216052
FOODB IDFDB022407
Wikipediasedoheptulose 7-phosphate
BioCyc IDD-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.
Protein Details
5. Sedoheptulose 1,7-bisphosphatase
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