ChemFOnt: Showing chemical card for Glucosamine 6-phosphate (CFc000000969)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:30 UTC

Chemfont ID

CFc000000969

Molecule Identification

Common Name

Glucosamine 6-phosphate

Definition

Glucosamine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose	ChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)	ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose	Generator
Glucosamine 6-phosphoric acid	Generator
a-D-Glucosamine 6-(dihydrogen phosphate)	Generator
a-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
α-D-Glucosamine 6-(dihydrogen phosphate)	Generator
α-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
2-Amino-2-deoxy-D-glucose 6-phosphate	HMDB
2-Amino-2-deoxyglucose 6-phosphate	HMDB
2-Amino-D-glucose-6-phosphate	HMDB
D-Glucosamine 6-phosphate	HMDB
D-Glucosamine phosphate	HMDB
D-Glucosamine-6-phosphate	HMDB
Glucosamine 6 -phosphate	HMDB
Glucosamine-6-P	HMDB
Glucosamine-6-phosphate	HMDB
Glucose-6-phosphorate	HMDB
Glucose-6-phosphoric acid	HMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester	HMDB
GLCN-6-P	MeSH, HMDB

Chemical Formula

C₆H₁₄NO₈P

Average Molecular Weight

259.151

Monoisotopic Molecular Weight

259.045702941

IUPAC Name

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

Traditional Name

α-D-glucosamine 6-phosphate

CAS Registry Number

55722-81-1

SMILES

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

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

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

Substituents

Hexose phosphate
Monosaccharide phosphate
Amino saccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Hemiacetal
1,2-diol
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Amine
Primary amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2-amino-2-deoxy-D-glucopyranose 6-phosphate (CHEBI:15873 )

Functional Ontology

Not Available

Placenta (HMDB: HMDB0001254)

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0001254)

Cytoplasm (HMDB: HMDB0001254)

Source

Endogenous

Endogenous (HMDB: HMDB0001254)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (HMDB: HMDB0001254)
Amino Sugar Metabolism (PathBank: SMP0063580)
Glutamate Metabolism (PathBank: SMP0087278)
Amino Sugar and Nucleotide Sugar Metabolism III (PathBank: SMP0121303)
Peptidoglycan Biosynthesis II (PathBank: SMP0122239)
Lipopolysaccharide Biosynthesis (PathBank: SMP0121299)
Peptidoglycan Biosynthesis I (PathBank: SMP0121305)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Lipopolysaccharide Biosynthesis II (PathBank: SMP0122112)
Lipopolysaccharide Biosynthesis III (PathBank: SMP0122237)
Amino Sugar and Nucleotide Sugar Metabolism II (PathBank: SMP0000906)
N-Acetylneuraminate, N-Acetylmannosamine, and N-Acetylglucosamine Degradation (PathBank: SMP0002044)
Amino Sugar and Nucleotide Sugar Metabolism (PathBank: SMP0002331)
Chitin Biosynthesis (PathBank: SMP0094667)

Disease pathway

4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Homocarnosinosis (HMDB: HMDB0001254)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Tay-Sachs Disease (PathBank: SMP0120545)
Homocarnosinosis (PathBank: SMP0120494)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001254)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	34.8 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	21.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon