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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:05 UTC
HMDB IDHMDB0000600
Secondary Accession Numbers
  • HMDB00600
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 ).
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
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
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
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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point257.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility63.3 g/LALOGPS
logP-3ALOGPS
logP-5.3ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)3.91ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.01 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbl-9331000000-55f681ebb00dbb5b63adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-01c0-3922126000-4608c9d1673267935e9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0319000000-e7265dc7d65b37c43370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c04-5934000000-12517f6dca52703813c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-7910000000-7645fde658d953975315View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0692000000-ce838deeac1950cd5317View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nu9-0961000000-0121d6fb23dab2a0d448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-6910000000-955acf234208503cf736View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen 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
NameSMPDB/PathwhizKEGG
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
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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011652
KNApSAcK IDNot Available
Chemspider ID17215976
KEGG Compound IDC05547
BioCyc IDPROCOLLAGEN-5-GALACTOSYLOXY-L-LYSINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5576
PubChem Compound22833535
PDB IDNot Available
ChEBI 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
  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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. .