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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-glyceraldehyde 3-phosphate and D-sedoheptulose 7-phosphate can be converted into D-erythrose 4-phosphate and β-D-fructofuranose 6-phosphate; which is catalyzed by the enzyme transaldolase. In addition, D-glyceraldehyde 3-phosphate and D-sedoheptulose 7-phosphate can be biosynthesized from 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 xylitol degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
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