Glucosylgalactosyl hydroxylysine (CHEM021848)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:56 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021848
Identification
Common NameGlucosylgalactosyl hydroxylysine
ClassSmall Molecule
DescriptionGlucosylgalactosyl hydroxylysine is a Glycoside of hydroxylysine. Hydroxylation of lysine is an important post-translational modification of collagen, (PMID 10928217) a reaction catalyzed by the enzyme Lysyl hydroxylase (EC 1.14.11.4) forming hydroxylysine in collagens and other proteins with collagen-like amino acid sequences, by the hydroxylation of lysine residues in X-lys-gly sequences. The hydroxylysine residues formed in the lysyl hydroxylase reaction have 2 important functions: first, their hydroxy groups serve as sites of attachment for carbohydrate units, either the monosaccharide galactose or the disaccharide glucosylgalactose; and second, they are essential for the stability of the intermolecular collagen crosslinks. (OMIM 153454) Hydroxylysine-deficient skin collagen is manifested in Ehlers-Danlos syndrome, type VIA, A heritable disorder of connective tissue (PMID 5016372) [HMDB]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2alpha-Glucosylgalactosyl-O-hydroxylysineHMDB
2-O-a-D-Glucopyranosyl-O-b-D-galactopyranosylhydroxylysineHMDB
2-O-alpha-D-Glucopyranosyl-O-beta-D-galactopyranosylhydroxylysineHMDB
2-O-alpha-delta-Glucopyranosyl-O-beta-delta-galactopyranosylhydroxylysineHMDB
5-[O-a-D-Glucopyranosyl-(1->2)-b-D-galactopyranosyloxy]-L-lysineHMDB
5-[O-alpha-D-Glucopyranosyl-(1->2)-beta-D-galactopyranosyloxy]-L-lysineHMDB
5-[O-alpha-delta-Glucopyranosyl-(1->2)-beta-delta-galactopyranosyloxy]-L-lysineHMDB
GlucopyranosylgalactopyranosylhydroxylysineHMDB
Glucosido-galactosyl-hydroxylysineHMDB
Glucosyl galactosyl-D-hydroxylysineHMDB
Glucosyl galactosyl-delta-hydroxylysineHMDB
GlucosylgalactosylhydroxylysineHMDB
Hydroxylysine-galactose-glucoseHMDB
Hydroxylysine-glucose-galactoseHMDB
L-5-((2-O-alpha-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy)-lysineHMDB
L-5-((2-O-alpha-delta-Glucopyranosyl-beta-delta-galactopyranosyl)oxy)-lysineHMDB
1,2 alpha-Glucosylgalactosyl-O-hydroxylysineHMDB
(2S)-2,6-Diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoateHMDB
Chemical FormulaC18H34N2O13
Average Molecular Mass486.468 g/mol
Monoisotopic Mass486.206 g/mol
CAS Registry Number32448-35-4
IUPAC Name(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid
Traditional Name(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid
SMILESNCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O
InChI IdentifierInChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1
InChI KeyUTIRJVJBKWSIOX-SRMFCGEKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Oxane
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Primary alcohol
  • Primary aliphatic amine
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • 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 Solubility82.2 g/LALOGPS
logP-3.6ALOGPS
logP-8ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)1.76ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area267.87 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity104 m³·mol⁻¹ChemAxon
Polarizability46.29 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-05q9-6125900000-0de572c676dd4f3e5e71Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0hh9-9500134000-e2f856e837ca6a15e9b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_69) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_31) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_101) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_171) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_172) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_173) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_200) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_215) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_71) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_72) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_73) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_184) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_186) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_297) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_298) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_301) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_307) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_308) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_327) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_342) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_349) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 30V, Positivesplash10-03fs-0910000000-79c09465fc3edc81cabeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07bb-0924600000-194b269d426da482f1f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bb-0922100000-f940966d1894b78b8a95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xs-1911000000-85b476e6f54ee25e2bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08g3-1904500000-c5212557085785075a62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0901100000-cb344df736c38c1e895dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-c93fab31d1d97345d410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0102900000-35cae597085109df5d12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdu-6903500000-ca992383cfddb3d00925Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9222000000-d094ca3b799998628fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0000900000-726c99d526e648fbee4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1902800000-7c98f8d7a23c2ffd7139Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9202100000-4d1e13c37067063c24ecSpectrum
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 IDHMDB0000585
FooDB IDFDB022130
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5567
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID109059
ChEBI ID89573
PubChem Compound ID122304
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Garza, Hector; Bennett, Nelson Jr.; Rodriguez, Gladys P. Improved rapid method for the isolation, purification and identification of collagen glycosides. Journal of Chromatography, A (1996), 732(2), 385-389.
2. Savolainen ER, Kero M, Pihlajaniemi T, Kivirikko KI: Deficiency of galactosylhydroxylysyl glucosyltransferase, an enzyme of collagen synthesis, in a family with dominant epidermolysis bullosa simplex. N Engl J Med. 1981 Jan 22;304(4):197-204.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. Ono S, Shimizu N, Imai T, Rodriguez GP: Urinary collagen metabolite excretion in amyotrophic lateral sclerosis. Muscle Nerve. 2001 Jun;24(6):821-5.
9. Rodriguez GP, Claus-Walker J: Measurement of hydroxylysine glycosides in urine and its application to spinal cord injury. J Chromatogr. 1984 Jun 8;308:65-73.
10. Szulc P, Seeman E, Delmas PD: Biochemical measurements of bone turnover in children and adolescents. Osteoporos Int. 2000;11(4):281-94.
11. Pinnell SR, Krane SM, Kenzora JE, Glimcher MJ: A heritable disorder of connective tissue. Hydroxylysine-deficient collagen disease. N Engl J Med. 1972 May 11;286(19):1013-20.
12. Bank, Ruud A., Beekman, B., Tenni, R., TeKoppele, Johan M. Pre-column derivatization method for the measurement of glycosylated hydroxylysines of collagenous proteins. Journal of Chromatography, B: Biomedical Sciences and Applications (1997), 703(1 + 2), 267-272
13. Kakimoto, Y., Akazawa, S. 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