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Record Information
Version3.6
Creation Date2008-08-11 15:28:31 UTC
Update Date2016-02-11 01:07:57 UTC
HMDB IDHMDB06790
Secondary Accession Numbers
  • HMDB06864
  • HMDB06934
Metabolite Identification
Common NameGalactosylglycerol
DescriptionGalactosylglycerol is an intermediate in galactose and glycerolipid metabolism (KEGG: C05401). In galactose metabolism, galactosylglycerol is reversibly produced from D-galactose and glycerol by the enzyme alpha-galactosidase [EC:3.2.1.22]. It is also the first to last step in the synthesis of glycerol and is converted from 1,2-diacyl-3-beta-D-galactosyl-sn-glycerol. It is then converted to glycerol via the enzyme beta-galactosidase [EC:3.2.1.23].
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S,5R,6R)-2-[(2R)-2,3-Dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triolHMDB
3-b-D-Galactosyl-sn-glycerolHMDB
3-beta-D-Galactosyl-sn-glycerolHMDB
3-beta-delta-Galactosyl-sn-glycerolHMDB
Azepan-2-oneHMDB
Chemical FormulaC9H18O8
Average Molecular Weight254.2344
Monoisotopic Molecular Weight254.100167552
IUPAC Name(2R,3R,4S,5R,6R)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namegalactosylglycerol
CAS Registry NumberNot Available
SMILES
OCC(O)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4?,5-,6+,7+,8-,9-/m1/s1
InChI KeyInChIKey=NHJUPBDCSOGIKX-VGPGGAHRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosylglycerols. These are glycerolipids structurally characterized by the presence of one or more sugar residues attached to glycerol via a glycosidic linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassGlycosylglycerols
Direct ParentGlycosylglycerols
Alternative Parents
Substituents
  • Glycosylglycerol
  • O-glycosyl compound
  • Glycosyl compound
  • Glycerol ether
  • Oxane
  • Monosaccharide
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility360.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.6ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area139.84 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.93 m3·mol-1ChemAxon
Polarizability24.27 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fabry diseaseSMP00525Not Available
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Gaucher DiseaseSMP00349Not Available
Globoid Cell LeukodystrophySMP00348Not Available
Krabbe diseaseSMP00526Not Available
Metachromatic Leukodystrophy (MLD)SMP00347Not Available
Sphingolipid MetabolismSMP00034map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
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 IDFDB024079
KNApSAcK IDNot Available
Chemspider ID570889
KEGG Compound IDC05401
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06790
Metagene LinkHMDB06790
METLIN IDNot Available
PubChem Compound656504
PDB IDNot Available
ChEBI ID15754
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Lipase with broad substrate specificity. Can hydrolyze both phospholipids and galactolipids. Acts preferentially on monoglycerides, phospholipids and galactolipids. Contributes to milk fat hydrolysis.
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Molecular weight:
52077.475
Reactions
1,2-diacyl-3-beta-D-galactosyl-sn-glycerol + Water → Galactosylglycerol + carboxylatesdetails
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available
Reactions
Galactosylglycerol + Water → Beta-D-Galactose + Glyceroldetails
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans. Isoform 2 has no beta-galactosidase catalytic activity, but plays functional roles in the formation of extracellular elastic fibers (elastogenesis) and in the development of connective tissue. Seems to be identical to the elastin-binding protein (EBP), a major component of the non-integrin cell surface receptor expressed on fibroblasts, smooth muscle cells, chondroblasts, leukocytes, and certain cancer cell types. In elastin producing cells, associates with tropoelastin intracellularly and functions as a recycling molecular chaperone which facilitates the secretions of tropoelastin and its assembly into elastic fibers.
Gene Name:
GLB1
Uniprot ID:
P16278
Molecular weight:
Not Available
General function:
Not Available
Specific function:
This protein is a minor sialoglycoprotein in erythrocyte membranes
Gene Name:
GYPB
Uniprot ID:
P06028
Molecular weight:
9795.6