Glucosamine 6-Phosphate
Basic information
- CAS
3616-42-0- Standard SMILES
N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COP(=O)(O)O)O[C@@H]1O- InChIKey
XHMJOUIAFHJHBW-UKFBFLRUSA-N- Molecular formula
- C6H14NO8P
- Average molar mass
- 259.15 g/mol
- Monoisotopic mass
- 259.0457034
Overview
Alpha-D-glucosamine 6-phosphate is a 2-amino-2-deoxy-D-glucopyranose 6-phosphate that has an alpha-configuration at the anomeric position. It has a role as a Saccharomyces cerevisiae metabolite and a human metabolite. It is functionally related to an alpha-D-glucosamine. It is a conjugate acid of an alpha-D-glucosamine 6-phosphate(1-).
Names & identifiers
- Preferred name
- Glucosamine 6-Phosphate
- IUPAC
- [(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
- English name
- D-Glucosamine 6-phosphate
- Molecular formula
- C6H14NO8P
- Molecular weight
- 259.15
Names & synonyms
glucosamine 6-phosphateGlcN-6-P[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methyl dihydrogen phosphate{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid(((2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl)methoxy)phosphonic acid((2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl)methyl dihydrogen phosphateRefChem:663121GlyTouCan:G97467RIG97467RID-glucosamine-6-phosphate2-amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranosealpha-D-glucosamine 6-phosphate
Show more names
GLUCOSAMINE-6-PHOSPHATEMethotrexate Impurity 24D-Glucosamine 6-phosphateGlucosamine Phosphate HydrateD-Glucosamine 6-phosphate >=98%D-Glucosamine 6-Phosphate Hydratealdehydo-D-glucosamine 6-phosphateD-Glucosamine 6-phosphateD-glucosamine 6-phosphate free acid
55722-81-11moqglucose 6-phosphorateGlucose-6-phosphoratebmse000189SCHEMBL4363568CHEBI:15873XHMJOUIAFHJHBW-UKFBFLRUSA-N
Properties
Computed structural properties
- XLogP
- -6.8
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 282
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
150 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
148.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
Physicochemical properties
- Melting point
- 127 °C · >127°C (dec.)
- Boiling point
- 652.2 · 652.2±65.0 °C(Predicted)
- Density
- 1.749 · 1.749±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Water (Slightly)
- pka
- 6.1 · pKa 6.10 /8.14(H2O,t = 26.3,c=0.01,N2)(Approximate)
- form
- Solid
- color
- White to Off-White
- biological source
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)
Applications
UsesD-Glucosamine 6-phosphate is an endogenous metabolite that can be synthesized by glutamine fructose-6-phosphate amidotransferase (GFAT). D-Glucosamine 6-phosphate can be used for the research of diabetes mellitus[1].
General DescriptionD-Glucosamine 6-phosphate, the natural form of glucosamine, is a monosaccharide produced during hexosamine biosynthesis pathway by the enzyme glucosamine-6-phosphate deaminase from the two substrates fructose 6-phosphate and glutamine.
Additional notes
DefinitionChEBI: The pyranose form of D-glucosamine 6-phosphate.
Related reactions
1 records
Compound notes
Loading…