Structure via PubChem · Public domain (PubChem)
D-mannoheptulose
Sign in to saveAlso known as D-manno-heptulose
Mannoheptulose is a heptose, a monosaccharide with seven carbon atoms, and a ketose, with the characteristic carbonyl group of the carbohydrate present on a secondary carbon (functioning as a ketone group). The sugar alcohol form of mannoheptulose is known as perseitol.
Chemical data
- Formula
- C7H14O7
- Molecular weight
- 210.18 g/mol
- IUPAC name
- (3S,4S,5R,6R)-1,3,4,5,6,7-hexahydroxyheptan-2-one
- SMILES
- C([C@H]([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O)O
- InChIKey
- HSNZZMHEPUFJNZ-QMTIVRBISA-N
- XLogP
- -3.9
- Polar surface area
- 138 Ų
- H-bond donors
- 6
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
110 papers- D-mannoheptulose phosphorylation by hexokinase isoenzymes.International journal of molecular medicine · 2001
- Uptake of D-mannoheptulose by rat erythrocytes, hepatocytes and parotid cells.International journal of molecular medicine · 2001
- Uptake of D-mannoheptulose by normal and tumoral pancreatic islet cells.International journal of molecular medicine · 2001
- Effects of D-mannoheptulose upon D-glucose metabolism in pancreatic B and non-B islet cells.International journal of molecular medicine · 2002
- D-mannoheptulose uptake and its metabolic and secretory effects in human pancreatic islets.International journal of molecular medicine · 2000
via PubMed
Wikidata facts
Show 9 more facts
- chemical formula
- C₇H₁₄O₇
- isomeric SMILES
- C([C@H]([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O)O
- canonical SMILES
- C(C(C(C(C(C(=O)CO)O)O)O)O)O
- found in taxon
- Papaver somniferum
- Commons category
- Mannoheptulose
- stereoisomer of
- sedoheptulose
- density
- 1.7
- refractive index
- 1.597
- melting point
- 149
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Inhibition of hexokinases
- Inhibition of insulin secretion
- Natural occurrence
- References
Mannoheptulose is a heptose, a monosaccharide with seven carbon atoms, and a ketose, with the characteristic carbonyl group of the carbohydrate present on a secondary carbon (functioning as a ketone group). The sugar alcohol form of mannoheptulose is known as perseitol.
==Inhibition of hexokinases== Mannoheptulose is a competitive and non-competitive inhibitor of both hexokinase and the related liver isozyme glucokinase. By blocking the enzyme hexokinase, it prevents glucose phosphorylation, the first step in the fundamental biochemical pathway of glycolysis. As a result, the breakdown of glucose is inhibited.
Excerpted from Wikipedia’s “D-mannoheptulose” article, available under the CC BY-SA 4.0 licence.