Showing metabocard for Glucose 1-phosphate (BMDB0001586)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (11) Show 11 proteinsXML
Show more...Show more...
Record Information
Version1.0
Creation Date2016-09-30 22:47:50 UTC
Update Date2020-06-04 20:50:42 UTC
BMDB IDBMDB0001586
Secondary Accession Numbers
  • BMDB01586
Metabolite Identification
Common NameGlucose 1-phosphate
DescriptionGalactose 1-phosphate, also known as delta-glucose 1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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 Nameglucose 1-phosphate
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
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
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 Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-003r-5591470000-4932aa0d35a53458633dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0390000000-9e3307d6125b74ed8579View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05mk-2960000000-4950cd68ef81b4267967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0230-5970000000-4c2745937c6f87f89f17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-03di-0090000000-3c372084bb61e1ef4257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0002-0090000000-90411431cffd98ebe09fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0090000000-9f2b4a83b1e7bad0b54bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0290000000-0701b77382bb89dff4e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000j-0980000000-3f1ea14f9deeb0503ccbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0920000000-1563a20c1e81bd3e405bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0f79-0960000000-861f86d1031c9d86f753View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0009000000-89f3bc29378643fb7eb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000i-0109000000-cdd8143c3ba06849c689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-05g0-0905000000-51b42ad0609cced943eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-05fr-0900000000-6d206170422cec07547cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-05fr-0900000000-96d8b3ec28a5f4f92dfdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-01b9-0509000000-83bba45a888d3e2c8b46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-006t-9600000000-e6e68c22e3002384468fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-0900000000-58fa2680157a4d69ead7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-0911000000-611d985a6a959222f903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-0a7885872856fe43526bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-b437590c213fb263989dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9100000000-97504a02d14244b901cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9360000000-98c3aee1d36863dc12abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-92ad15ffc9eae3eed039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581aeView in MoNA
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Muscle
  • Semimembranosus Muscle
  • Urine
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0001586
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001159
KNApSAcK IDNot Available
Chemspider ID388311
KEGG Compound IDC00103
BioCyc IDD-glucose-1-phosphates
BiGG ID33865
Wikipedia LinkGlucose-1-phosphate
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)Not Available
General References
  1. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  2. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  3. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details
1. Alpha-1,4 glucan phosphorylase
General function:
Carbohydrate transport and metabolism
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:
B0JYK6
Molecular weight:
97288.0
Enzyme Details
2. Glucose-6-phosphatase
General function:
Involved in glucose-6-phosphatase activity
Specific function:
Hydrolyzes glucose-6-phosphate to glucose in the endoplasmic reticulum. Forms with the glucose-6-phosphate transporter (SLC37A4/G6PT) the complex responsible for glucose production through glycogenolysis and gluconeogenesis. Hence, it is the key enzyme in homeostatic regulation of blood glucose levels (By similarity).
Gene Name:
G6PC
Uniprot ID:
Q29RU6
Molecular weight:
40827.0
Reactions
Glucose 1-phosphate + Water → D-Glucose + Hydrogen phosphatedetails
Enzyme Details
3. Phosphoglucomutase-1
General function:
Carbohydrate transport and metabolism
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:
PGM1
Uniprot ID:
Q08DP0
Molecular weight:
61589.0
Reactions
Glucose 1-phosphate → Glucose 6-phosphatedetails
Uridine diphosphate glucose → Glucose 1-phosphatedetails
Enzyme Details
4. Galactose-1-phosphate uridylyltransferase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
Q0V7N7
Molecular weight:
37812.0
Enzyme Details
5. Galactose-1-phosphate uridylyltransferase
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
Q58CX1
Molecular weight:
41288.0
Reactions
Uridine diphosphategalactose + Glucose 1-phosphate → Uridine diphosphate glucose + Galactose 1-phosphatedetails
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphatedetails
Uridine diphosphategalactose + Glucose 1-phosphate → Galactose 1-phosphate + Uridine diphosphate glucosedetails
Enzyme Details
6. UTP--glucose-1-phosphate uridylyltransferase
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q07130
Molecular weight:
56903.0
Reactions
Glucose 1-phosphate + Uridine triphosphate → Uridine diphosphate glucose + Pyrophosphatedetails
Uridine diphosphate glucose + Pyrophosphate → Glucose 1-phosphate + Uridine triphosphatedetails
Enzyme Details
7. Glycogen phosphorylase, brain form
General function:
Carbohydrate transport and metabolism
Specific function:
Glycogen phosphorylase that regulates glycogen mobilization. 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:
Q3B7M9
Molecular weight:
96340.0
Enzyme Details
8. Glycogen phosphorylase, liver form
General function:
Carbohydrate transport and metabolism
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 (By similarity).
Gene Name:
PYGL
Uniprot ID:
Q0VCM4
Molecular weight:
97456.0
Reactions
Glycogen + Hydrogen phosphate → Amylose + Glucose 1-phosphatedetails
Enzyme Details
9. Glycogen phosphorylase, muscle form
General function:
Carbohydrate transport and metabolism
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:
P79334
Molecular weight:
97293.0
Enzyme Details
10. PGM2L1 protein
General function:
Not Available
Specific function:
Not Available
Gene Name:
PGM2L1
Uniprot ID:
A5PKH8
Molecular weight:
70419.0
Reactions
Glucose 1-phosphate + Glyceric acid 1,3-biphosphate → Alpha-D-Glucose 1,6-bisphosphate + 3-Phosphoglyceric aciddetails
Enzyme Details
11. UDP-glucose 4-epimerase
General function:
Not Available
Specific function:
Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine. The reaction with UDP-Gal plays a critical role in the Leloir pathway of galactose catabolism in which galactose is converted to the glycolytic intermediate glucose 6-phosphate. It contributes to the catabolism of dietary galactose and enables the endogenous biosynthesis of both UDP-Gal and UDP-GalNAc when exogenous sources are limited. Both UDP-sugar interconversions are important in the synthesis of glycoproteins and glycolipids.
Gene Name:
GALE
Uniprot ID:
Q3T105
Molecular weight:
38254.0
Reactions
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphatedetails