Common Name6-phospho-d-gluconate
Description6-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconic acid-6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans. Within humans, 6-phosphogluconic acid participates in a number of enzymatic reactions. In particular, 6-phosphogluconic acid can be biosynthesized from gluconolactone; which is mediated by the enzyme 6-phosphogluconolactonase. In addition, 6-phosphogluconic acid can be converted into D-ribulose 5-phosphate through the action of the enzyme 6-phosphogluconate dehydrogenase, decarboxylating. In humans, 6-phosphogluconic acid is involved in the metabolic disorder called the transaldolase deficiency pathway. Outside of the human body, 6-Phosphogluconic acid has been detected, but not quantified in several different foods, such as cascade huckleberries, common chokecherries, half-highbush blueberries, american cranberries, and okra.
Structure
Molecular FormulaC6H13O10P
Average Mass276.13520
Monoisotopic Mass276.02463
IUPAC Name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
Traditional Name6-phosphogluconic acid
CAS Registry Number921-62-0
SMILESO=C([O-])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1
InChI KeyBIRSGZKFKXLSJQ-SQOUGZDYSA-N
CHEBI IDCHEBI:58759
HMDB IDHMDB0001316
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Warburg Effect
StateSolid
Water Solubility2.07e+01 g/l
logP-2.27
logS-1.12
pKa (Strongest Acidic)1.49
pKa (Strongest Basic)-3.54
Hydrogen Acceptor Count9
Hydrogen Donor Count7
Polar Surface Area184.98 Ų
Rotatable Bond Count7
Physiological Charge-3
Formal Charge0
Refractivity49.14 m³·mol⁻¹
Polarizability21.60

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