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Record Information
Version3.6
Creation Date2005-11-20 22:13:08 UTC
Update Date2014-10-29 20:42:15 UTC
HMDB IDHMDB01586
Secondary Accession Numbers
  • HMDB01306
Metabolite Identification
Common NameGlucose 1-phosphate
DescriptionThe direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. Free glucose 1-phosphate can also react with UTP to form UDP-glucose. It can then return to the greater glycogen structure via glycogen synthase.
Structure
Thumb
Synonyms
  1. a-D-Glucopyranosyl phosphate
  2. a-D-Glucose 1-phosphate
  3. alpha-D-Glucopyranosyl phosphate
  4. alpha-D-Glucose 1-phosphate
  5. alpha-D-Glucose-1-phosphate
  6. alpha-delta-Glucopyranosyl phosphate
  7. alpha-delta-Glucose 1-phosphate
  8. alpha-delta-Glucose-1-phosphate
  9. Cori ester
  10. D-Glucopyranose 1-phosphate
  11. D-Glucose 1-phosphate
  12. D-Glucose-1-P
  13. D-Glucose-1-phosphate
  14. delta-Glucopyranose 1-phosphate
  15. delta-Glucose 1-phosphate
  16. delta-Glucose-1-P
  17. delta-Glucose-1-phosphate
  18. Glucose 1-phosphate
  19. Glucose monophosphate
  20. Glucose-1-phosphate
  21. Glucose-1P
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Name[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
CAS Registry Number59-56-3
SMILES
OC[C@H]1OC(OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyHXXFSFRBOHSIMQ-GASJEMHNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility32.3 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8ChemAxon
Polarizability20.66ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue Location
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Lactose SynthesisSMP00444Not Available
Nucleotide Sugars MetabolismSMP00010map00520
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.32 +/- 0.69 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.07 +/- 0.26 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified0.94 +/- 0.22 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified2.26 +/- 2.53 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021830
KNApSAcK IDNot Available
Chemspider ID388311
KEGG Compound IDC00103
BioCyc IDGLC-1-P
BiGG ID33865
Wikipedia LinkGlucose 1-phosphate
NuGOwiki LinkHMDB01586
Metagene LinkHMDB01586
METLIN ID6331
PubChem Compound439165
PDB IDNot Available
ChEBI ID16077
References
Synthesis ReferenceWeinhausel, 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)Download (PDF)
General References
  1. Kamei A: Glycation and insolubility of human lens protein. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2787-91. Pubmed: 1464110
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. Kamei A, Kato M: Contribution of glycation to human lens coloration. Chem Pharm Bull (Tokyo). 1991 May;39(5):1272-6. Pubmed: 1914002
  8. 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
  9. 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
  10. Gannon MC, Khan MA, Nuttall FQ: Glucose appearance rate after the ingestion of galactose. Metabolism. 2001 Jan;50(1):93-8. Pubmed: 11172481
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
Reactions
Uridine diphosphate glucose + Water → Uridine 5'-monophosphate + Glucose 1-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
Reactions
Uridine diphosphate glucose + Water → Uridine 5'-monophosphate + Glucose 1-phosphatedetails
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:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
Reactions
(1,4-alpha-D-glucosyl)(n) + Phosphoric acid → (1,4-alpha-D-glucosyl)(n-1) + Glucose 1-phosphatedetails
Starch + Phosphoric acid → Amylose + Glucose 1-phosphatedetails
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:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355
Reactions
(1,4-alpha-D-glucosyl)(n) + Phosphoric acid → (1,4-alpha-D-glucosyl)(n-1) + Glucose 1-phosphatedetails
Starch + Phosphoric acid → Amylose + Glucose 1-phosphatedetails
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:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
Reactions
(1,4-alpha-D-glucosyl)(n) + Phosphoric acid → (1,4-alpha-D-glucosyl)(n-1) + Glucose 1-phosphatedetails
Starch + Phosphoric acid → Amylose + Glucose 1-phosphatedetails
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q16851
Molecular weight:
55676.36
Reactions
Uridine triphosphate + Glucose 1-phosphate → Pyrophosphate + Uridine diphosphate glucosedetails
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
P07902
Molecular weight:
43362.83
Reactions
Uridine diphosphate glucose + Galactose 1-phosphate → Glucose 1-phosphate + Uridine diphosphategalactosedetails
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Hydrolyzes UDP-glucose to glucose 1-phosphate and UMP and ADP-ribose to ribose 5-phosphate and AMP. The physiological substrate is probably UDP-glucose. Poor activity on other substrates such as ADP-glucose, CDP-glucose, GDP-glucose and GDP-mannose.
Gene Name:
NUDT14
Uniprot ID:
O95848
Molecular weight:
24118.085
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:
PGM1
Uniprot ID:
P36871
Molecular weight:
63789.985
Reactions
Glucose 1-phosphate → Glucose 6-phosphatedetails
Glucose 1-phosphate → Glucose 6-phosphatedetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P.
Gene Name:
PGM3
Uniprot ID:
O95394
Molecular weight:
62940.905
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GBA
Uniprot ID:
P04062
Molecular weight:
59715.745
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of the nucleoside breakdown products ribose-1-phosphate and deoxyribose-1-phosphate to the corresponding 5-phosphopentoses. May also catalyze the interconversion of glucose-1-phosphate and glucose-6-phosphate. Has low glucose 1,6-bisphosphate synthase activity.
Gene Name:
PGM2
Uniprot ID:
Q96G03
Molecular weight:
68282.765
Reactions
Glucose 1-phosphate → Glucose 6-phosphatedetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Glucose 1,6-bisphosphate synthase using 1,3-bisphosphoglycerate as a phosphate donor and a series of 1-phosphate sugars as acceptors, including glucose 1-phosphate, mannose 1-phosphate, ribose 1-phosphate and deoxyribose 1-phosphate. 5 or 6-phosphosugars are bad substrates, with the exception of glucose 6-phosphate. Also synthesizes ribose 1,5-bisphosphate. Has only low phosphopentomutase and phosphoglucomutase activities.
Gene Name:
PGM2L1
Uniprot ID:
Q6PCE3
Molecular weight:
70441.085
Reactions
Glyceric acid 1,3-biphosphate + Glucose 1-phosphate → 3-Phosphoglyceric acid + Alpha-D-Glucose 1,6-bisphosphatedetails
General function:
Not Available
Specific function:
Specific and highly efficient GDP-D-glucose phosphorylase regulating the levels of GDP-D-glucose in cells.
Gene Name:
GDPGP1
Uniprot ID:
Q6ZNW5
Molecular weight:
42362.06
Reactions
GDP-glucose + Phosphoric acid → Glucose 1-phosphate + Guanosine diphosphatedetails