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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:02 UTC
HMDB IDHMDB0000600
Secondary Accession Numbers
  • HMDB00600
Metabolite Identification
Common NameGalactosylhydroxylysine
DescriptionGalactosylhydroxylysine, also known as hydroxylysine-galactose, belongs to the class of organic compounds known as glycosyl-amino acids. Glycosyl-amino acids are compounds consisting of saccharide linked through a glycosyl linkage (O-, N-, or S-) to an amino acid. Galactosylhydroxylysine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make galactosylhydroxylysine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Galactosylhydroxylysine.
Structure
Thumb
Synonyms
ValueSource
5-(beta-D-Galactopyranosyloxy)-L-lysineHMDB
5-(beta-delta-Galactopyranosyloxy)-L-lysineHMDB
5-O-beta-D-Galactopyranosylhydroxy-L-lysineHMDB
5-O-beta-delta-Galactopyranosylhydroxy-L-lysineHMDB
beta-1-Galactosyl-O-hydroxylysineHMDB
Galactopyranosylhydroxy-L-lysineHMDB
Galactosyl-delta-hydroxylysineHMDB
Hydroxylysine-galactoseHMDB
L-5-(beta-D-Galactopyranosyloxy)-lysineHMDB
L-5-(beta-delta-Galactopyranosyloxy)-lysineHMDB
O-beta-D-Galactopyranosylhydroxy-L-lysineHMDB
O-beta-delta-Galactopyranosylhydroxy-L-lysineHMDB
Procollagen (5-galactosyloxy)-L-lysineHMDB
(2S)-6-Amino-2-{n-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoateHMDB
Chemical FormulaC12H24N2O8
Average Molecular Weight324.3276
Monoisotopic Molecular Weight324.153265754
IUPAC Name(2S)-6-amino-2-{N-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoic acid
Traditional Namegalactosylhydroxylysine
CAS Registry Number32448-36-5
SMILES
NCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C12H24N2O8/c13-4-2-1-3-6(12(19)20)14(21)11-10(18)9(17)8(16)7(5-15)22-11/h6-11,15-18,21H,1-5,13H2,(H,19,20)/t6-,7+,8-,9-,10+,11?/m0/s1
InChI KeyRCPOVANIIKXVTB-YPPRVYOWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosyl-amino acids. Glycosyl-amino acids are compounds consisting of saccharide linked through a glycosyl linkage (O-, N-, or S-) to an amino acid.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlycosyl-amino acids
Alternative Parents
Substituents
  • Glycosyl-amino-acid
  • Hexose monosaccharide
  • Glycosyl compound
  • N-glycosyl compound
  • N-hydroxyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Oxane
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Amino acid
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Oxacycle
  • N-organohydroxylamine
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point257.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.061 +/- 0.008 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.35 (0.45-2.3) umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.01 uMAdult (>18 years old)BothPaget's disease (osteitis deformans) details
UrineDetected and Quantified1.03 +/- 0.48 umol/mmol creatinineAdult (>18 years old)FemaleOsteoporosis details
UrineDetected and Quantified1.35 +/- 0.82 umol/mmol creatinineAdult (>18 years old)FemaleOsteoporosis details
Associated Disorders and Diseases
Disease References
Paget's disease
  1. Al-Dehaimi AW, Blumsohn A, Eastell R: Serum galactosyl hydroxylysine as a biochemical marker of bone resorption. Clin Chem. 1999 May;45(5):676-81. [PubMed:10222355 ]
Osteoporosis
  1. Lo Cascio V, Bertoldo F, Gambaro G, Gasperi E, Furlan F, Colapietro F, Lo Cascio C, Campagnola M: Urinary galactosyl-hydroxylysine in postmenopausal osteoporotic women: A potential marker of bone fragility. J Bone Miner Res. 1999 Aug;14(8):1420-4. [PubMed:10457275 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112162
KNApSAcK IDNot Available
Chemspider ID17215976
KEGG Compound IDC05547
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5576
PubChem Compound22833535
PDB IDNot Available
ChEBI ID165859
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000196
Good Scents IDNot Available
References
Synthesis ReferenceAdamczyk, Maciej; Reddy, Rajarathnam E.; Rege, Sushil D. Synthesis of galactosylhydroxylysine and its analogs. Synthetic Communications (2000), 30(18), 3281-3290.
Material Safety Data Sheet (MSDS)Not Available
General References