P. aeruginosa Metabolome Database: Glucosamine 6-phosphate (PAMDB000310)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000310

Identification

Name:

Glucosamine 6-phosphate

Description:

Glucosamine 6-phosphate is normally produced via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines. 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. (PMID 11270676, 11842094)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Amino-2-deoxy-D-glucose 6-phosphate
2-amino-2-Deoxy-D-glucose 6-phosphoric acid
2-Amino-2-deoxyglucose 6-phosphate
2-amino-2-Deoxyglucose 6-phosphoric acid
2-Amino-D-glucose-6-phosphate
2-amino-D-Glucose-6-phosphoric acid
D-Glucosamine 6-phosphate
D-Glucosamine 6-phosphoric acid
D-Glucosamine phosphate
D-Glucosamine phosphoric acid
D-glucosamine-6-P
D-Glucosamine-6-phosphate
D-Glucosamine-6-phosphoric acid
Glc-6P
Glucosamine 6 -phosphate
Glucosamine 6 -phosphoric acid
Glucosamine 6-Phosphate
Glucosamine 6-phosphoric acid
Glucosamine-6-P
Glucosamine-6-phosphate
Glucosamine-6-phosphoric acid
Glucose-6-phosphate
Glucose-6-phosphorate
Glucose-6-phosphoric acid
Phosphate mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester
Phosphorate mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester

Chemical Formula:

C₆H₁₄NO₈P

Average Molecular Weight:

259.151

Monoisotopic Molecular Weight:

259.045702941

InChI Key:

XHMJOUIAFHJHBW-UKFBFLRUSA-N

InChI:

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

CAS number:

3616-42-0

IUPAC Name:

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

Traditional IUPAC Name:

α-D-glucosamine 6-phosphate

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

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

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	34.8 mg/mL	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	20.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Amino sugar and nucleotide sugar metabolism pae00520
Galactose metabolism pae00052
Lipopolysaccharide biosynthesis pae00540
Metabolic pathways pae01100
Phosphotransferase system (PTS) pae02060

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0970000000-095ba413dfd29c80b445	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9500000000-e4e82ba86236d6046d0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-bd232a0933f76298e943	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03di-0190000000-778d1a36aaf5c9b3c846	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
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
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Wu, G., Haynes, T. E., Yan, W., Meininger, C. J. (2001). "Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine." Diabetologia 44:196-202. Pubmed: 11270676

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	15873
HMDB ID	HMDB01254
Pubchem Compound ID	439217
Kegg ID	C00352
ChemSpider ID	388356
Wikipedia ID	Not Available
BioCyc ID	D-GLUCOSAMINE-6-P
EcoCyc ID	D-GLUCOSAMINE-6-P
Ligand Expo	GLP

Enzymes

Protein Details

• Glucosamine--fructose-6-phosphate aminotransferase [isomerizing]

General function:: Involved in metabolic process
Specific function:: Catalyzes the first step in hexosamine metabolism, converting fructose-6P into glucosamine-6P using glutamine as a nitrogen source
Gene Name:: glmS
Locus Tag:: PA5549
Molecular weight:: 66.3 kDa

Reactions

L-glutamine + D-fructose 6-phosphate = L-glutamate + D-glucosamine 6-phosphate.

Protein Details

• Phosphoglucosamine mutase

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: Catalyzes the conversion of glucosamine-6-phosphate to glucosamine-1-phosphate. Can also catalyze the formation of glucose-6-P from glucose-1-P, although at a 1400-fold lower rate
Gene Name:: glmM
Locus Tag:: PA4749
Molecular weight:: 47.8 kDa

Reactions

Alpha-D-glucosamine 1-phosphate = D-glucosamine 6-phosphate.

Protein Details

• deacetylase of acs and cheY, regulates chemotaxis

General function:: Not Available
Specific function:: Not Available
Gene Name:: cobB
Locus Tag:: PA1273
Molecular weight:: 46.5 kDa

Glucosamine 6-phosphate (PAMDB000310)

Structure for Glucosamine 6-phosphate (PAMDB000310)

Enzymes

Reactions

Reactions

Transporters