Common NameD-mannose 6-phosphate
DescriptionMannose 6-phosphate, also known as alpha-D-mannose-6-p or man-6-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. Mannose 6-phosphate exists in all eukaryotes, ranging from yeast to humans. Within humans, mannose 6-phosphate participates in a number of enzymatic reactions. In particular, mannose 6-phosphate can be converted into fructose 6-phosphate through its interaction with the enzyme mannose-6-phosphate isomerase. In addition, mannose 6-phosphate can be biosynthesized from D-mannose through the action of the enzyme hexokinase-1. Mannose 6-phosphate is a potent competitive inhibitor of pinocytosis of human platelet beta-glucuronidase and it is a necessary component of the recognition marker on the enzyme for pinocytosis by human fibroblasts as well (PMID 908752 ). In humans, mannose 6-phosphate is involved in fructose intolerance, hereditary.
Structure
Molecular FormulaC6H13O9P
Average Mass260.13580
Monoisotopic Mass260.02972
IUPAC Name{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4s,5s,6r)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number3672-15-9
SMILESO=P([O-])([O-])OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1
InChI KeyNBSCHQHZLSJFNQ-RWOPYEJCSA-N
CHEBI IDCHEBI:58735
HMDB IDHMDB0001078
Pathways
NameSMPDB/PathBank
Fructose and mannose metabolism
Fructosuria
Fructose intolerance, hereditary
StateSolid
Water Solubility3.14e+01 g/l
logP-2.06
logS-0.92
pKa (Strongest Acidic)1.22
pKa (Strongest Basic)-3.65
Hydrogen Acceptor Count8
Hydrogen Donor Count6
Polar Surface Area156.91 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity46.80 m³·mol⁻¹
Polarizability20.43

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