Galactosylhydroxylysine (CHEM021849)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:57 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021849
Identification
Common NameGalactosylhydroxylysine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass324.328 g/mol
Monoisotopic Mass324.153 g/mol
CAS Registry Number32448-36-5
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
SMILESNCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability31.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbl-9331000000-55f681ebb00dbb5b63adSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-01c0-3922126000-4608c9d1673267935e9eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positivesplash10-03fs-0900000000-b277425c7b2baf2e1ce0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0319000000-e7265dc7d65b37c43370Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c04-5934000000-12517f6dca52703813c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-7910000000-7645fde658d953975315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0692000000-ce838deeac1950cd5317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nu9-0961000000-0121d6fb23dab2a0d448Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-6910000000-955acf234208503cf736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-feb8033fade4ec36b163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1900000000-9887ff59cd8b2608215eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9500000000-2e6b65bbf11b1b8a689fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0309000000-6517fbb0bf566b43f2d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5769000000-812154ea65e633cab3a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-4900000000-d6a34ed61253e7556f1dSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000600
FooDB IDFDB112162
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5576
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17215976
ChEBI ID165859
PubChem Compound ID22833535
Kegg Compound IDC05547
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Adamczyk, Maciej; Reddy, Rajarathnam E.; Rege, Sushil D. Synthesis of galactosylhydroxylysine and its analogs. Synthetic Communications (2000), 30(18), 3281-3290.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. Moro, L., Romanello, M. Galactosylhydroxylysine and bone metabolism: an updated review. Cells and Materials (1997), 7(4), 329-332
15. 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