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Record Information
Version3.6
Creation Date2006-05-22 15:12:42 UTC
Update Date2016-10-26 14:57:41 UTC
HMDB IDHMDB03219
Secondary Accession NumbersNone
Metabolite Identification
Common NameSedoheptulose
DescriptionSedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature. Sedoheptulose is a seven-carbon ketose sugar originally found in Sedum spectabile, a common perennial garden plant. Later it was shown to be widely distributed in the plants of the Crassulaceae family. The Crassulaceae, or orpine family, is a family of dicotyledons. They store water in their succulent leaves. They are found worldwide, but mostly occur in the Northern Hemisphere and southern Africa, typically in dry and/or cold areas where water may be scarce. The family includes about 1,400 species in 33 genera. As a result, this sugar is often found to be part of the human diet. This sugar, D-sedoheptulose (I), is a significant intermediary compound in the cyclic regeneration of D-ribulose. It also plays an important role as a transitory compound in the cyclic regeneration of D-ribulose for carbon dioxide fixation in plant photosynthesis. -- www.accessscience.com.
Structure
Thumb
Synonyms
ValueSource
altro-HeptuloseHMDB
D-altro-2-HeptuloseHMDB
D-altro-Hept-2-uloseHMDB
VolemuloseHMDB
Chemical FormulaC7H14O7
Average Molecular Weight210.1819
Monoisotopic Molecular Weight210.073952802
IUPAC Name1,3,4,5,6,7-hexahydroxyheptan-2-one
Traditional NameD-manno-heptulose
CAS Registry Number3019-74-7
SMILES
OCC(O)C(O)C(O)C(O)C(=O)CO
InChI Identifier
InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2
InChI KeyInChIKey=HSNZZMHEPUFJNZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility227.0 mg/mLALOGPS
logP-2.4ALOGPS
logP-3.9ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.52 m3·mol-1ChemAxon
Polarizability19.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0490000000-630d8c36c508e095915aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-bb285bc9b51a479a9bd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-07xr-9100000000-fe7ae48092a9feb86e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4890000000-de864d6b52cf2915034dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-9f02301f86e653ed6635View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9100000000-3e8b16c4d5925087b599View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap4-9820000000-5c6ebc4e0e5aaadffddaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdu-9400000000-0dc5533e380eda3a379eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-dacc8fdb74c2e64e2cedView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004279
KNApSAcK IDC00001132
Chemspider ID92980
KEGG Compound IDC02076
BioCyc IDCPD-3614
BiGG IDNot Available
Wikipedia LinkSedoheptulose
NuGOwiki LinkHMDB03219
Metagene LinkHMDB03219
METLIN ID3344
PubChem Compound102926
PDB IDNot Available
ChEBI ID130460
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pitkanen E, Sahlstrom K: The occurrence of sedoheptulose in human urine. Ann Med Exp Biol Fenn. 1968;46(3):295-300. [5731228 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:
TKTL1
Uniprot ID:
P51854
Molecular weight:
59302.195
General function:
Involved in catalytic activity
Specific function:
Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:
TALDO1
Uniprot ID:
P37837
Molecular weight:
37539.74
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
KHK
Uniprot ID:
P50053
Molecular weight:
32730.055
Reactions
Adenosine triphosphate + Sedoheptulose → ADP + Sedoheptulose 1-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis.
Gene Name:
TKTL2
Uniprot ID:
Q9H0I9
Molecular weight:
67876.625
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Acts as a modulator of macrophage activation through control of glucose metabolism (By similarity).
Gene Name:
SHPK
Uniprot ID:
Q9UHJ6
Molecular weight:
51504.425
Reactions
Adenosine triphosphate + Sedoheptulose → ADP + D-Sedoheptulose 7-phosphatedetails