Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:34:01 UTC
Update Date2024-04-20 06:11:56 UTC
Metabolite IDMMDBc0033083
Metabolite Identification
Common NameD-fructose 1-phosphate
DescriptionFructose 1-phosphate, also known as D-fructose-1-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. Metabolism of fructose thus essentially results in intermediates of glycolysis. The final product of glycolysis (pyruvate) may then undergo gluconeogenesis, enter the TCA cycle or be stored as fatty acids. Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, fructose 1-phosphate participates in a number of enzymatic reactions. In particular, fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. Because fructokinase has a high Vmax fructose entering cells is quickly phosphorylated to fructose 1-phosphate. In humans, fructose 1-phosphate is involved in fructose intolerance, hereditary. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It is generated mainly by hepatic fructokinase but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule. Aldolase B converts it into glyceraldehyde and dihydroxyacetone phosphate (DHAP). Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness.
Structure
Synonyms
ValueSource
1-O-Phosphono-D-fructoseChEBI
D-Fructose 1-phosphoric acidGenerator
D-Fructose 1-phosphateChEBI
Fructose-1-phosphoric acidGenerator
Molecular FormulaC6H13O9P
Average Mass260.1358
Monoisotopic Mass260.029718526
IUPAC Name{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]oxy}phosphonic acid
Traditional Namefructose 1-phosphate
CAS Registry Number15978-08-2
SMILES
[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1
InChI KeyZKLLSNQJRLJIGT-UYFOZJQFSA-N