You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:48 UTC
HMDB IDHMDB01068
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Sedoheptulose 7-phosphate
DescriptionD-Sedoheptulose 7-phosphate is an intermediate of the Pentose phosphate pathway (PPP) that has two functions: the generation of NADPH for reductive syntheses and oxidative stress responses within cells, and the formation of ribose residues for nucleotide and nucleic acid biosynthesis. (PMID 16055050 )It is formed by transketolase and acted upon (degraded) by transaldolase. Sedoheptulose 7-phosphate can be increased in the blood of patients affected with a transaldolase deficiency (TALDO1; EC 2.2.1.2). (PMID 12881455 ) Sedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature. (wikipedia).
Structure
Thumb
Synonyms
ValueSource
7-(Dihydrogen phosphate) sedoheptuloseHMDB
D-Sedoheptulose-7-PHMDB
D-Sedoheptulose-7-phosphateHMDB
Heptulose-7-phosphateHMDB
Sedoheptulose 7-phosphateHMDB
Sedoheptulose-7-PHMDB
Sedoheptulose-7-phosphateHMDB
Chemical FormulaC7H15O10P
Average Molecular Weight290.1618
Monoisotopic Molecular Weight290.040283212
IUPAC Name{[(2R,3S,4R,5S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5S)-3,4,5,6-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]methoxyphosphonic acid
CAS Registry Number2646-35-7
SMILES
OCC1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=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
InChI KeyInChIKey=CBIDVWSRUUODHL-QTSLKERKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
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 Solubility30.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.2 m3·mol-1ChemAxon
Polarizability23.55 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Glucose-6-phosphate dehydrogenase deficiencySMP00518Not Available
Pentose Phosphate PathwaySMP00031map00030
Ribose-5-phosphate isomerase deficiencySMP00519Not Available
Transaldolase deficiencySMP00520Not Available
Warburg EffectSMP00654Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.15 +/- 0.66 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified0.89 +/- 0.41 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified74.9 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified1.15 +/- 0.44 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.299 +/- 0.236 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.360 +/- 1.20 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.19 +/- 0.84 uMAdult (>18 years old)BothTransaldolase deficiency details
SalivaDetected and Quantified0.91 +/- 0.26 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified0.84 +/- 0.13 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified1.60 +/- 1.55 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  1. Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [12881455 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022407
KNApSAcK IDNot Available
Chemspider ID17216052
KEGG Compound IDC00281
BioCyc IDD-SEDOHEPTULOSE-7-P
BiGG ID34485
Wikipedia Linksedoheptulose 7-phosphate
NuGOwiki LinkHMDB01068
Metagene LinkHMDB01068
METLIN ID5980
PubChem Compound22833559
PDB IDNot Available
ChEBI ID15721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. [15882454 ]
  2. Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. [16055050 ]
  3. Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [12881455 ]
  4. Thornalley PJ, Jahan I, Ng R: Suppression of the accumulation of triosephosphates and increased formation of methylglyoxal in human red blood cells during hyperglycaemia by thiamine in vitro. J Biochem (Tokyo). 2001 Apr;129(4):543-9. [11275553 ]
  5. Makarov SA, Kudriavtseva GV, Kolotilova AI: [Effect of prostaglandins F2 and F2 alpha on the pentosephosate pathway in human blood platelets] Vopr Med Khim. 1983 Sep-Oct;29(5):27-32. [6316661 ]

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
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Aminofructose 6-phosphate + D-Ribose 5-phosphate → Iminoerythrose 4-phosphate + D-Sedoheptulose 7-phosphatedetails
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
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Fructose 6-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Beta-D-Fructose 6-phosphatedetails
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
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Aminofructose 6-phosphate + D-Ribose 5-phosphate → Iminoerythrose 4-phosphate + D-Sedoheptulose 7-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
Reactions
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Aminofructose 6-phosphate + D-Ribose 5-phosphate → Iminoerythrose 4-phosphate + D-Sedoheptulose 7-phosphatedetails
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