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Identification
YMDB IDYMDB00044
NameGlucosamine 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlucosamine 6-phosphate is produced by the enzyme fructose 6-phosphate amidotransferase from L-glutamine amide and D-fructose 6-phosphate.
Structure
Thumb
Synonyms
  • 2-amino-2-Deoxy-6-O-phosphono-a-D-glucopyranose
  • 2-amino-2-Deoxy-6-O-phosphono-alpha-D-glucopyranose
  • 2-amino-2-Deoxy-6-O-phosphono-α-D-glucopyranose
  • 2-Amino-2-deoxy-D-glucose 6-phosphate
  • 2-Amino-2-deoxyglucose 6-phosphate
  • 2-Amino-D-glucose-6-phosphate
  • a-D-Glucosamine 6-(dihydrogen phosphate)
  • a-D-Glucosamine 6-(dihydrogen phosphoric acid)
  • alpha-D-Glucosamine 6-(dihydrogen phosphate)
  • alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)
  • D-Glucosamine 6-phosphate
  • D-Glucosamine phosphate
  • D-Glucosamine-6-phosphate
  • GLCN-6-P
  • Glucosamine 6 -phosphate
  • Glucosamine 6-Phosphate
  • Glucosamine 6-phosphate, disodium salt
  • Glucosamine 6-phosphate, monosodium salt
  • Glucosamine 6-phosphic acid
  • Glucosamine 6-phosphoric acid
  • glucosamine-6-P
  • glucosamine-6-phosphate
  • Glucose-6-phosphorate
  • Glucose-6-phosphoric acid
  • Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester
  • α-D-glucosamine 6-(dihydrogen phosphate)
  • α-D-glucosamine 6-(dihydrogen phosphoric acid)
  • Α-D-glucosamine 6-(dihydrogen phosphate)
  • Α-D-glucosamine 6-(dihydrogen phosphoric acid)
CAS number3616-42-0
WeightAverage: 259.151
Monoisotopic: 259.045702941
InChI KeyXHMJOUIAFHJHBW-UKFBFLRUSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameα-D-glucosamine 6-phosphate
Chemical FormulaC6H14NO8P
SMILES[H]O[C@@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])N([H])[H]
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
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability20.95 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Amino sugar and nucleotide sugar metabolismec00520 Map00520
SMPDB Reactions
Beta-D-Fructose 6-phosphate + L-GlutamineGlucosamine 6-phosphate + L-Glutamic acid
Glucosamine 6-phosphate + Acetyl-CoACoenzyme A + hydron + N-acetyl-D-glucosamine 6-phosphate
KEGG Reactions
water + Glucosamine 6-phosphateFructose 6-phosphate + Ammonium
Fructose 6-phosphate + L-GlutamineL-Glutamic acid + Glucosamine 6-phosphate
Acetyl-CoA + Glucosamine 6-phosphateN-acetyl-D-glucosamine 6-phosphate + hydron + Coenzyme A
alpha-D-glucosamine 1-phosphateGlucosamine 6-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Dummitt, B., Micka, W. S., Chang, Y. H. (2005). "Yeast glutamine-fructose-6-phosphate aminotransferase (Gfa1) requires methionine aminopeptidase activity for proper function." J Biol Chem 280:14356-14360.15699032
  • Mio, T., Yamada-Okabe, T., Arisawa, M., Yamada-Okabe, H. (1999). "Saccharomyces cerevisiae GNA1, an essential gene encoding a novel acetyltransferase involved in UDP-N-acetylglucosamine synthesis." J Biol Chem 274:424-429.9867860
  • Watzele, G., Tanner, W. (1989). "Cloning of the glutamine:fructose-6-phosphate amidotransferase gene from yeast. Pheromonal regulation of its transcription." J Biol Chem 264:8753-8758.2656689
Synthesis Reference:Cacioppo, F.; Pandolfo, L.; Arena, E. Synthesis of glucosamine 6-phosphate in tissues of rachitic rats. Giorn. Biochim. (1964), 13(4), 249-55.
External Links:
ResourceLink
CHEBI ID15873
HMDB IDHMDB01254
Pubchem Compound ID439217
Kegg IDC00352
ChemSpider ID25056834
FOODB IDFDB022515
Wikipedia IDNot Available
BioCyc IDD-GLUCOSAMINE-6-P

Enzymes

General function:
Involved in metabolic process
Specific function:
Involved in amino sugar synthesis (formation of chitin, supplies the amino sugars of asparagine-linked oligosaccharides of glycoproteins)
Gene Name:
Not Available
Uniprot ID:
A2P2R3
Molecular weight:
29272.0
Reactions
L-glutamine + D-fructose 6-phosphate → L-glutamate + D-glucosamine 6-phosphate.
General function:
Involved in metabolic process
Specific function:
Involved in amino sugar synthesis (formation of chitin, supplies the amino sugars of asparagine-linked oligosaccharides of glycoproteins)
Gene Name:
GFA1
Uniprot ID:
P14742
Molecular weight:
80046.0
Reactions
L-glutamine + D-fructose 6-phosphate → L-glutamate + D-glucosamine 6-phosphate.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P
Gene Name:
PCM1
Uniprot ID:
P38628
Molecular weight:
62066.10156
Reactions
N-acetyl-alpha-D-glucosamine 1-phosphate → N-acetyl-D-glucosamine 6-phosphate.
General function:
Involved in N-acetyltransferase activity
Specific function:
Acetyl-CoA + D-glucosamine 6-phosphate = CoA + N-acetyl-D-glucosamine 6-phosphate
Gene Name:
GNA1
Uniprot ID:
P43577
Molecular weight:
18134.80078
Reactions
Acetyl-CoA + D-glucosamine 6-phosphate → CoA + N-acetyl-D-glucosamine 6-phosphate.