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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:56 UTC
NP-MRD IDNP0001436
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlucosamine 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
Thumb
Synonyms
ValueSource
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranoseChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranoseGenerator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranoseGenerator
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
Glucosamine 6-phosphoric acidGenerator
2-Amino-2-deoxy-D-glucose 6-phosphateHMDB
2-Amino-2-deoxyglucose 6-phosphateHMDB
2-Amino-D-glucose-6-phosphateHMDB
D-Glucosamine 6-phosphateHMDB
D-Glucosamine phosphateHMDB
D-Glucosamine-6-phosphateHMDB
Glucosamine 6 -phosphateHMDB
Glucosamine-6-pHMDB
Glucosamine-6-phosphateHMDB
Glucose-6-phosphorateHMDB
Glucose-6-phosphoric acidHMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) esterHMDB
GLCN-6-pHMDB
Chemical FormulaC6H14NO8P
Average Mass259.1510 Da
Monoisotopic Mass259.04570 Da
IUPAC Name{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Nameα-D-glucosamine 6-phosphate
CAS Registry Number3616-42-0
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 KeyXHMJOUIAFHJHBW-UKFBFLRUSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility34.8 g/LALOGPS
logP-2.6ALOGPS
logP-4.2ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability21.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001254
DrugBank IDDB02657
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022515
KNApSAcK IDC00019580
Chemspider ID388356
KEGG Compound IDC00352
BioCyc IDCPD-13469
BiGG ID34709
Wikipedia LinkNot Available
METLIN ID6111
PubChem Compound439217
PDB IDNot Available
ChEBI ID15873
Good Scents IDNot Available
References
General References
  1. Wu G, Haynes TE, Yan W, Meininger CJ: Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. Diabetologia. 2001 Feb;44(2):196-202. [PubMed:11270676 ]
  2. Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP: Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate. J Biol Chem. 2002 Apr 26;277(17):14764-70. Epub 2002 Feb 12. [PubMed:11842094 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  4. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  5. Furchak JR, Yang P, Jennings C, Walter NG, Kennedy RT: Assay for glucosamine 6-phosphate using a ligand-activated ribozyme with fluorescence resonance energy transfer or CE-laser-induced fluorescence detection. Anal Chem. 2008 Nov 1;80(21):8195-201. doi: 10.1021/ac801410k. Epub 2008 Oct 9. [PubMed:18842060 ]