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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameGalactosylhydroxylysine
DescriptionGalactosylhydroxylysine is released during bone resorption and elevated in subjects with metabolic bone loss. Galactosylhydroxylysine is a sensitive and specific marker of bone resorption. (PMID 10222355 ).
Procollagen (5-galactosyloxy)-L-lysineHMDB
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosyl-amino acids. These 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
  • Glycosyl-amino-acid
  • N-hydroxyl-alpha-amino acid
  • N-glycosyl compound
  • Glycosyl compound
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Oxane
  • Monosaccharide
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • N-organohydroxylamine
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point257.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility63.3 mg/mLALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.94 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.01 m3·mol-1ChemAxon
Polarizability31.73 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
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 Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Blood Platelet
  • Embryo
  • Fetus
  • IMR-90 Cells (Fetal Lung Diploid Fibroblasts)
  • Skin (Cultured Fibroblasts)
  • WI-38 Cells (Fetal Lung Diploid Fibroblasts)
PathwaysNot Available
Normal Concentrations
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
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
  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. [10457275 ]
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. [10222355 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011652
KNApSAcK IDNot Available
Chemspider ID17215976
KEGG Compound IDC05547
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00600
Metagene LinkHMDB00600
PubChem Compound22833535
PDB IDNot Available
ChEBI IDNot Available
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
  1. Kelleher PC: Urinary excretion of hydroxyproline, hydroxylysine and hydroxylysine glycosides by patients with Paget's disease of bone and carcinoma with metastases in bone. Clin Chim Acta. 1979 Mar 15;92(3):373-9. [436278 ]
  2. Schroder CH, Monnens LA, van Lith-Zanders HM, Trijbels JM, Veerkamp JH: The urinary excretion of total hydroxylysine and its glycosides in normal persons, and in patients suffering from Alport's syndrome--contribution of the peptide-bound fraction. Nephron. 1987;47(4):253-7. [3696326 ]
  3. Schroder CH, Langeveld JP, van Raay-Selten BH, Trijbels FJ, de Graaf R, Veerkamp JH, Monnens LA: Urinary excretion of hydroxylysine and its glycosides in normal persons of different ages--influence of maturation. Int J Pediatr Nephrol. 1985 Oct-Dec;6(4):239-44. [2419268 ]
  4. Schroder CH, Monnens LA, van Lith-Zanders HM, Trijbels JM, Veerkamp JH, Langeveld JP: Urinary excretion of hydroxylysine and its glycosides in Alport's syndrome and several other glomerulopathies. Nephron. 1986;44(2):103-7. [3774073 ]
  5. Grazioli V, Alfano M, Stenico A, Casari E: Urinary output of hydroxylysine glycosides and pyridinium cross-links in detecting rat bone collagen turnover rate. FEBS Lett. 1996 Jun 17;388(2-3):134-8. [8690072 ]
  6. Marabini R, Sirtori P, Chionna R, Barzizza L, Rubinacci A: Galactosylhydroxylysine and pyridinium cross links in monitoring the bone response to hormone replacement therapy. J Endocrinol Invest. 1996 Mar;19(3):154-8. [8743280 ]
  7. Leigh SD, Ju HS, Lundgard R, Daniloff GY, Liu V: Development of an immunoassay for urinary galactosylhydroxylysine. J Immunol Methods. 1998 Nov 1;220(1-2):169-78. [9839938 ]
  8. Sirtori P, Sosio C, Polo RM, Tenni R, Rubinacci A: A comparative study on biochemical markers of bone collagen breakdown in post-menopausal women. Pharmacol Res. 1997 Sep;36(3):229-35. [9367668 ]
  9. LoCascio V, Braga V, Bertoldo F, Bettica P, Pasini AF, Stefani L, Moro L: Effect of bisphosphonate therapy and parathyroidectomy on the urinary excretion of galactosylhydroxylysine in primary hyperparathyroidism. Clin Endocrinol (Oxf). 1994 Jul;41(1):47-51. [8050131 ]
  10. 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. [10222355 ]
  11. Casetta B, Romanello M, Moro L: A rapid and simple method for quantitation of urinary hydroxylysyl glycosides, indicators of collagen turnover, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(23):2238-41. [11114034 ]
  12. Plebani M, Bernardi D, Meneghetti MF, Ujka F, Zaninotto M: Biological variability in assessing the clinical value of biochemical markers of bone turnover. Clin Chim Acta. 2000 Sep;299(1-2):77-86. [10900294 ]
  13. Moro, L., Romanello, M. Galactosylhydroxylysine and bone metabolism: an updated review. Cells and Materials (1997), 7(4), 329-332
  14. Kakimoto, Y., Akazawa, Shigenori. Isolation and identification of NG,NG- and NG,N'G-dimethylarginine, N -mono-, di-, and trimethyllysine, and glucosylgalactosyl- and galactosyl- -hydroxylysine from human urine. Journal of Biological Chemistry (1970), 245(21), 5751-8