P. aeruginosa Metabolome Database: Glucose 1-phosphate (PAMDB000423)

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

PAMDB000423

Identification

Name:

Glucose 1-phosphate

Description:

Glucose 1-phosphate is the direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. Glycogen phosphorylase, the product of the glgP Gene, catalyzes glycogen breakdown by removing glucose units from the nonreducing ends in Pseudomonas aeruginosa. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose, by using the enzyme UDP-glucose pyrophosphorylase. Periplasmic acid glucose-1-phosphatase (G-1-Pase) encoded by gene Agp is necessary for the growth of Pseudomonas aeruginosa in a minimal medium containing glucose-1-phosphate (G-1-P) as the sole source of carbon.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-D-glucose-1-P
α-glucose-1-phosphate
α-glucose-1-phosphoric acid
A-D-Glucopyranosyl phosphate
a-D-Glucopyranosyl phosphoric acid
A-D-Glucose 1-phosphate
a-D-Glucose 1-phosphoric acid
a-D-Glucose-1-P
A-D-Glucose-1-phosphate
a-D-Glucose-1-phosphoric acid
a-delta-Glucopyranosyl phosphate
a-delta-Glucopyranosyl phosphoric acid
a-delta-Glucose 1-phosphate
a-delta-Glucose 1-phosphoric acid
a-delta-Glucose-1-phosphate
a-delta-Glucose-1-phosphoric acid
a-Glucose-1-phosphate
a-Glucose-1-phosphoric acid
a-δ-Glucopyranosyl phosphate
a-δ-Glucopyranosyl phosphoric acid
a-δ-Glucose 1-phosphate
a-δ-Glucose 1-phosphoric acid
a-δ-Glucose-1-phosphate
a-δ-Glucose-1-phosphoric acid
Alpha-D-Glucopyranosyl phosphate
alpha-D-Glucopyranosyl phosphoric acid
Alpha-D-Glucose 1-phosphate
alpha-D-Glucose 1-phosphoric acid
Alpha-D-Glucose-1-P
Alpha-D-Glucose-1-phosphate
alpha-D-Glucose-1-phosphoric acid
Alpha-delta-Glucopyranosyl phosphate
alpha-delta-Glucopyranosyl phosphoric acid
Alpha-delta-Glucose 1-phosphate
alpha-delta-Glucose 1-phosphoric acid
Alpha-delta-glucose-1-phosphate
alpha-delta-Glucose-1-phosphoric acid
Alpha-Glucose-1-phosphate
alpha-Glucose-1-phosphoric acid
Cori ester
D-Glucopyranose 1-phosphate
D-Glucopyranose 1-phosphoric acid
D-Glucose 1-phosphate
D-Glucose 1-phosphoric acid
D-glucose-α-1-phosphate
D-Glucose-α-1-phosphoric acid
D-Glucose-1-P
D-Glucose-1-phosphate
D-Glucose-1-phosphoric acid
D-Glucose-a-1-phosphate
D-Glucose-a-1-phosphoric acid
D-Glucose-alpha-1-phosphate
D-Glucose-alpha-1-phosphoric acid
D-Glucose-α-1-phosphate
D-Glucose-α-1-phosphoric acid
Delta-Glucopyranose 1-phosphate
delta-Glucopyranose 1-phosphoric acid
Delta-Glucose 1-phosphate
delta-Glucose 1-phosphoric acid
Delta-Glucose-1-P
Delta-Glucose-1-phosphate
delta-Glucose-1-phosphoric acid
Glucose 1-phosphate
Glucose 1-phosphoric acid
Glucose monophosphate
Glucose monophosphoric acid
Glucose-1-phosphate
Glucose-1-phosphoric acid
Glucose-1P
α-D-Glucopyranosyl phosphate
α-D-Glucopyranosyl phosphoric acid
α-D-Glucose 1-phosphate
α-D-Glucose 1-phosphoric acid
α-D-Glucose-1-P
α-D-Glucose-1-phosphate
α-D-Glucose-1-phosphoric acid
α-Glucose-1-phosphate
α-Glucose-1-phosphoric acid
α-δ-Glucopyranosyl phosphate
α-δ-Glucopyranosyl phosphoric acid
α-δ-Glucose 1-phosphate
α-δ-Glucose 1-phosphoric acid
α-δ-Glucose-1-phosphate
α-δ-Glucose-1-phosphoric acid
δ-Glucopyranose 1-phosphate
δ-Glucopyranose 1-phosphoric acid
δ-Glucose 1-phosphate
δ-Glucose 1-phosphoric acid
δ-Glucose-1-P
δ-Glucose-1-phosphate
δ-Glucose-1-phosphoric acid

Chemical Formula:

C₆H₁₃O₉P

Average Molecular Weight:

260.1358

Monoisotopic Molecular Weight:

260.029718526

InChI Key:

HXXFSFRBOHSIMQ-VFUOTHLCSA-N

InChI:

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1

CAS number:

59-56-3

IUPAC Name:

{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional IUPAC Name:

α-D-glucose 1-phosphate

SMILES:

OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](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

Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Secondary alcohol
Polyol
1,2-diol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranose 1-phosphate (CHEBI:29042 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	1000.0 mg/mL [MERCK INDEX (1996)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	32.3 mg/mL	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol^-1	ChemAxon
Polarizability	20.72 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:

Water + Glucose 1-phosphate > Phosphate + D-glucose
Glycogen + Phosphate <> a limit dextrin + Glucose 1-phosphate
Glucose 1-phosphate <> α-D-glucose 6-phosphate
Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate
a 1,4-α-D-glucan + Phosphate <> a 1,4-α-D-glucan + Glucose 1-phosphate
Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate
Phosphate <> Glucose 1-phosphate
Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose
Galactose 1-phosphate + Galactose 1-phosphate > Glucose 1-phosphate
Galactose 1-phosphate + UDP-Glucose + Galactose 1-phosphate > Uridine diphosphategalactose + Glucose 1-phosphate + Uridine diphosphategalactose
Thymidine 5'-triphosphate + Hydrogen ion + Glucose 1-phosphate > Pyrophosphate + dTDP-D-Glucose

More...

Pathways:

Amino sugar and nucleotide sugar metabolism pae00520
Galactose metabolism pae00052
Glycolysis / Gluconeogenesis pae00010
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Pentose and glucuronate interconversions pae00040
Pentose phosphate pathway pae00030
Polyketide sugar unit biosynthesis pae00523
Purine metabolism pae00230
Starch and sucrose metabolism pae00500
Streptomycin biosynthesis pae00521

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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	13C NMR Spectrum	Not Available

References

References:

Arthur PG, Kent JC, Hartmann PE: Microanalysis of the metabolic intermediates of lactose synthesis in human milk and plasma using bioluminescent methods. Anal Biochem. 1989 Feb 1;176(2):449-56. Pubmed: 2742136
Bollaert PE, Levy B, Nace L, Laterre PF, Larcan A: Hemodynamic and metabolic effects of rapid correction of hypophosphatemia in patients with septic shock. Chest. 1995 Jun;107(6):1698-701. Pubmed: 7781370
Chen YT, Kato T: Liver-specific glucose-6-phosphatase is not present in human placenta. J Inherit Metab Dis. 1985;8(2):92-4. Pubmed: 3023746
Gannon MC, Khan MA, Nuttall FQ: Glucose appearance rate after the ingestion of galactose. Metabolism. 2001 Jan;50(1):93-8. Pubmed: 11172481
Gella FJ, Cusso R: Glycogen phosphorylase from normal and leukemic human leucocytes: kinetic parameters of the active form. Rev Esp Fisiol. 1980 Mar;36(1):1-6. Pubmed: 7394270
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
Kamei A, Kato M: Contribution of glycation to human lens coloration. Chem Pharm Bull (Tokyo). 1991 May;39(5):1272-6. Pubmed: 1914002
Kamei A: Glycation and insolubility of human lens protein. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2787-91. Pubmed: 1464110
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
Kodentsova VM, Glinka EIu: [Changes in kinetic properties of pyridoxal-dependent enzymes during dietary vitamin B6 deficiency in rats] Ukr Biokhim Zh. 1990 Jan-Feb;62(1):44-9. Pubmed: 2110692
Krause EG, Will H, Bohm M, Wollenberger A: The assay of glycogen phosphorylase in human blood serum and its application to the diagnosis of myocardial infarction. Clin Chim Acta. 1975 Jan 20;58(2):145-54. Pubmed: 1122638
Lai K, Elsas LJ: Structure-function analyses of a common mutation in blacks with transferase-deficiency galactosemia. Mol Genet Metab. 2001 Sep-Oct;74(1-2):264-72. Pubmed: 11592823
Lang A, Groebe H, Hellkuhl B, von Figura K: A new variant of galactosemia: galactose-1-phosphate uridylytransferase sensitive to product inhibition by glucose 1-phosphate. Pediatr Res. 1980 May;14(5):729-34. Pubmed: 6247691
Lederer B, Van Hoof F, Van den Berghe G, Hers H: Glycogen phosphorylase and its converter enzymes in haemolysates of normal human subjects and of patients with type VI glycogen-storage disease. A study of phosphorylase kinase deficiency. Biochem J. 1975 Apr;147(1):23-35. Pubmed: 168880
Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. Pubmed: 11439108
Mahadevan-Jansen A, Mitchell MF, Ramanujam N, Malpica A, Thomsen S, Utzinger U, Richards-Kortum R: Near-infrared Raman spectroscopy for in vitro detection of cervical precancers. Photochem Photobiol. 1998 Jul;68(1):123-32. Pubmed: 9679458
Nakashima H, Suo H, Ochiai J, Sugie H, Kawamura Y: [A case of adult onset phosphoglucomutase deficiency] Rinsho Shinkeigaku. 1992 Jan;32(1):42-7. Pubmed: 1385770
Palombi M, Bochicchio O, Gargiulo M, Sammarco M: [Alternative therapy of deep venous thrombosis in patients at hemorrhagic risk] Minerva Chir. 1994 Mar;49(3):189-94. Pubmed: 8028729
Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
Pezzarossa A, Cavazzini G, Coscelli C, Butturini U: [Modifications induced by glucose-1-phosphate on carbohydrate utilization curve after venous loading. Results in normal subjects (preliminary note)] Boll Soc Ital Biol Sper. 1972 Jun 30;48(12):318-21. Pubmed: 5070100
Reinken L, Obladen M, Dockx-Reinken F, Lindemann C: [The effect of osteopenia prevention in very small premature infants on hormonal parameters of calcium metabolism and bone mineralization] Klin Padiatr. 1989 May-Jun;201(3):177-82. Pubmed: 2739343
Suzuki K, Kayamori Y, Katayama Y: Development of an enzymatic method for the assay of serum magnesium using phosphoglucomutase and glucose-6-phosphate dehydrogenase. Clin Biochem. 1991 Jun;24(3):249-53. Pubmed: 1831412
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
Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. Pubmed: 2018547

Synthesis Reference:

Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	29042
HMDB ID	HMDB01586
Pubchem Compound ID	65533
Kegg ID	C00103
ChemSpider ID	388311
Wikipedia	Glucose 1-phosphate
BioCyc ID	GLC-1-P
EcoCyc ID	GLC-1-P

Enzymes

Protein Details

• Glycogen phosphorylase

General function:: Involved in phosphorylase activity
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
Gene Name:: glgP
Locus Tag:: PA2144
Molecular weight:: 92 kDa

Reactions

(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.

Protein Details

• UTP--glucose-1-phosphate uridylyltransferase_

General function:: Involved in UTP:glucose-1-phosphate uridylyltransferase activity
Specific function:: May play a role in stationary phase survival
Gene Name:: galU
Locus Tag:: PA2023
Molecular weight:: 31.2 kDa

Reactions

UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.

Protein Details

• Protein mazG

General function:: Involved in nucleoside-triphosphate diphosphatase activity
Specific function:: Specific function unknown
Gene Name:: mazG
Locus Tag:: PA0935
Molecular weight:: 31.2 kDa

Reactions

ATP + H(2)O = AMP + diphosphate.

Protein Details

• Phosphoglucomutase

General function:: Involved in intramolecular transferase activity, phosphotransferases
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:: pgm
Locus Tag:: PA5131
Molecular weight:: 55.6 kDa

Reactions

Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate.

Protein Details

• Glucose-1-phosphate thymidylyltransferase 1

General function:: Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:: Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:: rmlA1
Locus Tag:: PA5163
Molecular weight:: 32.5 kDa

Reactions

dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.

Glucose 1-phosphate (PAMDB000423)

Structure for Glucose 1-phosphate (PAMDB000423)

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters