Showing metabocard for Galactose 1-phosphate (BMDB0000645)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:12 UTC
Update Date2020-06-04 20:29:23 UTC
BMDB IDBMDB0000645
Secondary Accession Numbers
  • BMDB00645
Metabolite Identification
Common NameGalactose 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-alpha-D-galactopyranoseChEBI
alpha-D-Gal-1-pChEBI
alpha-D-Galactopyranose 1-phosphateChEBI
alpha-D-Galactopyranose, 1-(dihydrogen phosphate)ChEBI
alpha-D-Galactopyranosyl phosphateChEBI
alpha-D-Galactosyl phosphateChEBI
Galactose-1-phosphateChEBI
1-O-Phosphono-a-D-galactopyranoseGenerator
1-O-Phosphono-α-D-galactopyranoseGenerator
a-D-Gal-1-pGenerator
Α-D-gal-1-pGenerator
a-D-Galactopyranose 1-phosphateGenerator
a-D-Galactopyranose 1-phosphoric acidGenerator
alpha-D-Galactopyranose 1-phosphoric acidGenerator
Α-D-galactopyranose 1-phosphateGenerator
Α-D-galactopyranose 1-phosphoric acidGenerator
a-D-Galactopyranose, 1-(dihydrogen phosphate)Generator
a-D-Galactopyranose, 1-(dihydrogen phosphoric acid)Generator
alpha-D-Galactopyranose, 1-(dihydrogen phosphoric acid)Generator
Α-D-galactopyranose, 1-(dihydrogen phosphate)Generator
Α-D-galactopyranose, 1-(dihydrogen phosphoric acid)Generator
a-D-Galactopyranosyl phosphateGenerator
a-D-Galactopyranosyl phosphoric acidGenerator
alpha-D-Galactopyranosyl phosphoric acidGenerator
Α-D-galactopyranosyl phosphateGenerator
Α-D-galactopyranosyl phosphoric acidGenerator
a-D-Galactosyl phosphateGenerator
a-D-Galactosyl phosphoric acidGenerator
alpha-D-Galactosyl phosphoric acidGenerator
Α-D-galactosyl phosphateGenerator
Α-D-galactosyl phosphoric acidGenerator
Galactose-1-phosphoric acidGenerator
Galactose 1-phosphoric acidGenerator
a-D-Galactose-1-phosphateHMDB
a-D-Galactose-1-phosphoric acidHMDB
alpha-D-Galactose-1-phosphoric acidHMDB
Α-D-galactose-1-phosphateHMDB
Α-D-galactose-1-phosphoric acidHMDB
Galactose-1-phosphate, (beta-L-gal)-isomerHMDB
Galactose-1-phosphate, 14C-labeledHMDB
Galactose-1-phosphate, disilver (+1) salt, (D-gal)-isomerHMDB
Galactose-1-phosphate, sodium saltHMDB
Galactose-1-phosphate, (beta-D-gal)-isomerHMDB
1-(Dihydrogen phosphate) galactitolHMDB
1-Phosphate a-D-galactopyranoseHMDB
a-D-1-(Dihydrogen phosphate) galactopyranoseHMDB
a-D-Galactose 1-phosphateHMDB
alpha-D-1-(Dihydrogen phosphate) galactopyranoseHMDB
alpha-D-Galactose 1-phosphateHMDB
D-Galactose 1-phosphateHMDB
Galactopyranose 1-phosphateHMDB
D-Galactopyranose 1-phosphateHMDB
D-Galactopyranose 1-phosphoric acidHMDB
D-Galactose 1-phosphoric acidHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Namegalactose 1 phosphate
CAS Registry Number2255-14-3
SMILES
OC[C@H]1O[C@H](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-FPRJBGLDSA-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 SolubilityNot AvailableNot 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
Polarizability20.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Erythrocyte
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified561 - 2070 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000645
DrugBank IDDB02317
Phenol Explorer Compound IDNot Available
FooDB IDFDB001159
KNApSAcK IDC00007391
Chemspider IDNot Available
KEGG Compound IDC00446
BioCyc IDGALACTOSE-1P
BiGG IDNot Available
Wikipedia LinkGalactose_1-phosphate
METLIN IDNot Available
PubChem Compound123912
PDB IDNot Available
ChEBI ID17973
References
Synthesis ReferenceChen Jie; Yager Claire; Reynolds Robert; Palmieri Michael; Segal Stanton Erythrocyte galactose 1-phosphate quantified by isotope-dilution gas chromatography-mass spectrometry. Clinical chemistry (2002), 48(4), 604-12.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  2. 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 ]
  3. 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 ]
  4. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  5. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Enzymes

Enzyme Details
1. Galactokinase
General function:
Carbohydrate transport and metabolism
Specific function:
Major enzyme for galactose metabolism.
Gene Name:
GALK1
Uniprot ID:
A6H768
Molecular weight:
42227.0
Reactions
D-Galactose + Adenosine triphosphate → Galactose 1-phosphate + ADPdetails
Enzyme Details
2. 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
3. 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
4. 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