FComEx: Glucosamine 6-phosphate (PC000620)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:32 UTC

Update date

2017-01-19 02:36:30 UTC

FoodComEx ID

PC000620

FoodDB Record

FDB022515

Chemical Information

Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate is normally produced in endothelial cells via the 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. 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) [HMDB]

CAS Number

3616-42-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-amino-2-Deoxy-6-O-ONO-a-D-glucopyranose	Generator
2-amino-2-Deoxy-6-O-ONO-alpha-D-glucopyranose	ChEBI
2-amino-2-Deoxy-6-O-ONO-α-D-glucopyranose	Generator
2-amino-2-Deoxy-D-glucose 6-ate	HMDB
2-Amino-2-deoxy-D-glucose 6-phosphate	hmdb
2-amino-2-Deoxyglucose 6-ate	HMDB
2-Amino-2-deoxyglucose 6-phosphate	hmdb
2-amino-D-Glucose-6-ate	HMDB
2-Amino-D-glucose-6-phosphate	hmdb
a-D-Glucosamine 6-(dihydrogen ate)	Generator
a-D-Glucosamine 6-(dihydrogen ic acid)	Generator
alpha-D-Glucosamine 6-(dihydrogen ate)	ChEBI
alpha-D-Glucosamine 6-(dihydrogen ic acid)	Generator
D-Glucosamine 6-ate	HMDB
D-Glucosamine 6-phosphate	hmdb
D-Glucosamine ate	HMDB
D-Glucosamine phosphate	hmdb
D-Glucosamine-6-ate	HMDB
D-Glucosamine-6-phosphate	hmdb
Glucosamine 6 -ate	HMDB
Glucosamine 6 -phosphate	hmdb
GLUCOSAMINE 6-ATE	ChEBI
GLUCOSAMINE 6-ic acid	Generator
Glucosamine 6-Phosphate	hmdb
Glucosamine 6-phosphic acid	hmdb
Glucosamine-6-ate	HMDB
glucosamine-6-P	hmdb
glucosamine-6-phosphate	hmdb
Glucose-6-orate	HMDB
Glucose-6-oric acid	HMDB
Glucose-6-phosphorate	hmdb
Glucose-6-phosphoric acid	hmdb
Oric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester	HMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester	hmdb
α-D-glucosamine 6-(dihydrogen ate)	Generator
α-D-glucosamine 6-(dihydrogen ic acid)	Generator

Chemical Formula

C6H14NO8P

IUPAC name

{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid

InChI Identifier

InChI=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 Key

XHMJOUIAFHJHBW-UKFBFLRUSA-N

Isomeric SMILES

N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O

Average Molecular Weight

259.151

Monoisotopic Molecular Weight

259.045702941

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents