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Human Metabolome Database Version 3.5

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Showing metabocard for Glucose 1-phosphate (HMDB01586)

Record Information
Version 3.5
Creation Date 2005-11-20 15:13:08 -0700
Update Date 2013-02-08 17:10:48 -0700
HMDB ID HMDB01586
Secondary Accession Numbers
  • HMDB01306
Metabolite Identification
Common Name Glucose 1-phosphate
Description The 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name [(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
CAS Registry Number 59-56-3
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 Key HXXFSFRBOHSIMQ-GASJEMHNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Starch and sucrose metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 32.3 g/L ALOGPS
LogP -2.00 ALOGPS
LogP -3.1 ChemAxon
LogS -0.91 ALOGPS
pKa (strongest acidic) 1.16 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.8 ChemAxon
Polarizability 20.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
Pathways
Name SMPDB Link KEGG Link
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Lactose Synthesis SMP00444 Not Available
Glycolysis SMP00040 map00010 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Nucleotide Sugars Metabolism SMP00010 map00520 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021830
KNApSAcK ID Not Available
Chemspider ID 388311 Link_out
KEGG Compound ID C00103 Link_out
BioCyc ID GLC-1-P Link_out
BiGG ID 33865 Link_out
Wikipedia Link Glucose 1-phosphate Link_out
NuGOwiki Link HMDB01586 Link_out
Metagene Link HMDB01586 Link_out
METLIN ID 6331 Link_out
PubChem Compound 439165 Link_out
PDB ID Not Available
ChEBI ID 16077 Link_out
References
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) 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  7. Kamei A, Kato M: Contribution of glycation to human lens coloration. Chem Pharm Bull (Tokyo). 1991 May;39(5):1272-6. Pubmed: 1914002 Link_out
  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 Link_out
  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 Link_out
  10. Gannon MC, Khan MA, Nuttall FQ: Glucose appearance rate after the ingestion of galactose. Metabolism. 2001 Jan;50(1):93-8. Pubmed: 11172481 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP1
Uniprot ID: P22413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 3
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP3
Uniprot ID: O14638 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, liver form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGL
Uniprot ID: P06737 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, muscle form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGM
Uniprot ID: P11217 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, brain form
Reactions:
  • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
Gene Name: PYGB
Uniprot ID: P11216 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UTP--glucose-1-phosphate uridylyltransferase
Reactions:
  • UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose [RN:R00289]
Gene Name: UGP2
Uniprot ID: Q16851 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactose-1-phosphate uridylyltransferase
Reactions:
  • UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose [RN:R00955]
Gene Name: GALT
Uniprot ID: P07902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine diphosphate glucose pyrophosphatase
Reactions:
  • UDP-sugar + H2O = UMP + alpha-D-aldose 1-phosphate [RN:R03986]
Gene Name: NUDT14
Uniprot ID: O95848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglucomutase-1
Reactions:
  • alpha-D-glucose 1-phosphate = D-glucose 6-phosphate [RN:R08639]
Gene Name: PGM1
Uniprot ID: P36871 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoacetylglucosamine mutase
Reactions:
  • N-acetyl-alpha-D-glucosamine 1-phosphate = N-acetyl-D-glucosamine 6-phosphate [RN:R08193]
Gene Name: PGM3
Uniprot ID: O95394 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosylceramidase
Reactions:
  • D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498]
Gene Name: GBA
Uniprot ID: P04062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoglucomutase-2
Reactions:
  • alpha-D-ribose 1-phosphate = D-ribose 5-phosphate [RN:R01057]
Gene Name: PGM2
Uniprot ID: Q96G03 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose 1,6-bisphosphate synthase
Reactions:
  • 3-phospho-D-glyceroyl phosphate + alpha-D-glucose 1-phosphate = 3-phospho-D-glycerate + alpha-D-glucose 1,6-bisphosphate [RN:R01660]
Gene Name: PGM2L1
Uniprot ID: Q6PCE3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA