Showing metabocard for Glucose 1-phosphate (BMDB0001586)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:50 UTC
Update Date2020-06-04 20:50:42 UTC
MCDB ID BMDB0001586
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
ValueSource
1-O-Phosphono-D-glucopyranoseChEBI
Cori esterChEBI
D-Glucose 1-phosphateChEBI
GLC-1-pChEBI
D-Glucose 1-phosphoric acidGenerator
Glucose 1-phosphoric acidGenerator
a-D-Glucopyranosyl phosphateHMDB
a-D-Glucose 1-phosphateHMDB
alpha-D-Glucopyranosyl phosphateHMDB
alpha-D-Glucose 1-phosphateHMDB
alpha-D-Glucose-1-phosphateHMDB
alpha-delta-Glucopyranosyl phosphateHMDB
alpha-delta-Glucose 1-phosphateHMDB
alpha-delta-Glucose-1-phosphateHMDB
D-Glucopyranose 1-phosphateHMDB
D-Glucose-1-pHMDB
D-Glucose-1-phosphateHMDB
delta-Glucopyranose 1-phosphateHMDB
delta-Glucose 1-phosphateHMDB
delta-Glucose-1-pHMDB
delta-Glucose-1-phosphateHMDB
Glucose monophosphateHMDB
Glucose-1-phosphateHMDB
Glucose-1PHMDB
Galactose 1-phosphoric acidHMDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-ee60e23a7f8053dae6d32016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-003r-5591470000-4932aa0d35a53458633d2017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0390000000-9e3307d6125b74ed85792012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05mk-2960000000-4950cd68ef81b42679672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0230-5970000000-4c2745937c6f87f89f172012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-03di-0090000000-3c372084bb61e1ef42572020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0002-0090000000-90411431cffd98ebe09f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0090000000-9f2b4a83b1e7bad0b54b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0290000000-0701b77382bb89dff4e22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000j-0980000000-3f1ea14f9deeb0503ccb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0920000000-1563a20c1e81bd3e405b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0f79-0960000000-861f86d1031c9d86f7532020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0009000000-89f3bc29378643fb7eb72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000i-0109000000-cdd8143c3ba06849c6892020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-05g0-0905000000-51b42ad0609cced943ea2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-05fr-0900000000-6d206170422cec07547c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-05fr-0900000000-96d8b3ec28a5f4f92dfd2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-01b9-0509000000-83bba45a888d3e2c8b462020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-006t-9600000000-e6e68c22e3002384468f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-0900000000-58fa2680157a4d69ead72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-0911000000-611d985a6a959222f9032020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9240000000-0a7885872856fe43526b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9240000000-b437590c213fb263989d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-9100000000-97504a02d14244b901cb2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9360000000-98c3aee1d36863dc12ab2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-92ad15ffc9eae3eed0392016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfc211275bafe42581ae2016-09-12View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified58 +/- 2 uM details
Detected and Quantified43 +/- 3 uM details
Detected and Quantified43 +/- 11 uM details
Detected and Quantified55 +/- 3 uM details
Detected and Quantified87 +/- 129 uM details
Detected and Quantified28 +/- 28 uM details
Detected and Quantified53 +/- 28 uM details
Detected and Quantified3.844 uM details
Detected and Quantified55 +/- 3 uM details
Detected and Quantified58 +/- 2 uM details
Detected and Quantified43 +/- 3 uM details
Detected and Quantified43 +/- 11 uM details
HMDB IDHMDB0001586
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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.