Showing Metabocard for D-glucosamine 6-phosphate (BASm0003660)

Common NameD-glucosamine 6-phosphate
DescriptionGlucosamine 6-phosphate (CAS: 3616-42-0) is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is a member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID:11270676 , 11842094 ).
Structure
Molecular FormulaC6H14NO8P
Average Mass259.15100
Monoisotopic Mass259.04570
IUPAC Name{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r,6s)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number55722-81-1
SMILES[NH3+][C@H]1C(O)O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1
InChI KeyXHMJOUIAFHJHBW-UKFBFLRUSA-N
CHEBI IDCHEBI:58725
HMDB IDHMDB0001254
Pathways
NameSMPDB/PathBank
Amino Sugar Metabolism
Glutamate Metabolism
2-Hydroxyglutric Aciduria (D And L Form)
Sialuria or French Type Sialuria
Salla Disease/Infantile Sialic Acid Storage Disease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Homocarnosinosis
Tay-Sachs Disease
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease
Succinic semialdehyde dehydrogenase deficiency
StateSolid
Water Solubility3.48e+01 g/l
logP-2.60
logS-0.87
pKa (Strongest Acidic)1.22
pKa (Strongest Basic)8.23
Hydrogen Acceptor Count8
Hydrogen Donor Count6
Polar Surface Area162.7 Ų
Rotatable Bond Count3
Physiological Charge-1
Formal Charge0
Refractivity48.45 m³·mol⁻¹
Polarizability20.95

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