Showing metabocard for 5-Hydroxylysine (BMDB0000450)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:56 UTC
Update Date2020-05-11 20:36:58 UTC
BMDB IDBMDB0000450
Secondary Accession Numbers
  • BMDB00450
Metabolite Identification
Common Name5-Hydroxylysine
Description5-Hydroxylysine, also known as lysine, 5 hydroxy, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 5-Hydroxylysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. In cattle, 5-hydroxylysine is involved in the metabolic pathway called the lysine degradation pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S,5R)-5-HydroxylysineChEBI
(5R)-5-Hydroxy-L-lysineChEBI
alpha,epsilon-Diamino-delta-hydroxycaproic acidChEBI
L-Erythro-5-hydroxylysineChEBI
L-Normal-5-hydroxylysineChEBI
5-Hydroxy-L-lysineKegg
a,epsilon-Diamino-delta-hydroxycaproateGenerator
a,epsilon-Diamino-delta-hydroxycaproic acidGenerator
alpha,epsilon-Diamino-delta-hydroxycaproateGenerator
Α,epsilon-diamino-δ-hydroxycaproateGenerator
Α,epsilon-diamino-δ-hydroxycaproic acidGenerator
Lysine, 5 hydroxyMeSH
2,6-Diamino-5-hydroxyhexanoic acidMeSH
5 HydroxylysineMeSH
HydroxylysineMeSH
(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acidMeSH
2,6 Diamino 5 hydroxyhexanoic acidMeSH
a,epsilon-diamino-δ-hydroxycaproateGenerator, HMDB
a,epsilon-diamino-δ-hydroxycaproic acidGenerator, HMDB
(2S,5R)-2,6-diamino-5-HydroxyhexanoateHMDB
5-Hydroxy-lysineHMDB
D-Hydroxy-L-lysineHMDB
D-HydroxylysineHMDB
delta-DL-HydroxylysineHMDB
delta-Hydroxy-L-lysineHMDB
delta-HydroxylysineHMDB
erythro-5-Hydroxy-L-lysineHMDB
Hydroxy-lysineHMDB
L-D-HydroxylysineHMDB
L-delta-HydroxylysineHMDB
Procollagen 5-hydroxy-L-lysineHMDB
Procollagen L-erythro-5-hydroxy-L-lysineHMDB
5-HYDROXYLYSINEChEBI
Chemical FormulaC6H14N2O3
Average Molecular Weight162.187
Monoisotopic Molecular Weight162.100442324
IUPAC Name(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid
Traditional NameL-hydroxylysine
CAS Registry Number1190-94-9
SMILES
NC[C@H](O)CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1
InChI KeyYSMODUONRAFBET-UHNVWZDZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • 1,2-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility23 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.8ALOGPS
logP-4.4ChemAxon
logS-0.12ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.17 m³·mol⁻¹ChemAxon
Polarizability16.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000450
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012682
KNApSAcK IDNot Available
Chemspider ID2297721
KEGG Compound IDC16741
BioCyc IDCPD-14226
BiGG ID53055
Wikipedia LinkHydroxylysine
METLIN ID5439
PubChem Compound3032849
PDB IDNot Available
ChEBI ID18040
References
Synthesis ReferenceAllevi, P.; Anastasia, M. Synthesis of all four possible stereoisomers of 5-hydroxylysine. Tetrahedron: Asymmetry (2000), 11(15), 3151-3160.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]