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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:20 UTC
HMDB IDHMDB0001422
Secondary Accession Numbers
  • HMDB01422
Metabolite Identification
Common Name3-Hydroxy-N6,N6,N6-trimethyl-L-lysine
Description3-Hydroxy-N6,N6,N6-trimethyl-L-lysine 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. 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine is a very strong basic compound (based on its pKa). 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. Within humans, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine participates in a number of enzymatic reactions. In particular, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid can be biosynthesized from N6,N6,N6-trimethyl-L-lysine and oxoglutaric acid through its interaction with the enzyme trimethyllysine dioxygenase, mitochondrial. In addition, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine can be converted into glycine and 4-trimethylammoniobutanal through its interaction with the enzyme serine hydroxymethyltransferase, cytosolic. In humans, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine is involved in carnitine synthesis.
Structure
Data?1582752200
Synonyms
ValueSource
3-Hydroxy-N(6),N(6),N(6)-trimethyl-L-lysineHMDB
3-Hydroxy-N(6),N(6),N(6)-trimethyllysineHMDB
3-Hydroxy-N6,N6,N6-trimethyl-L-lysin-N6-iumHMDB
Chemical FormulaC9H21N2O3
Average Molecular Weight205.2746
Monoisotopic Molecular Weight205.155217548
IUPAC Name[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium
Traditional Name[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)CCCC(O)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C9H20N2O3/c1-11(2,3)6-4-5-7(12)8(10)9(13)14/h7-8,12H,4-6,10H2,1-3H3/p+1/t7?,8-/m0/s1
InChI KeyZRJHLGYVUCPZNH-MQWKRIRWSA-O
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 hydroxy acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Hydroxy acid
  • Fatty acid
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic salt
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.83 g/LALOGPS
logP-2.9ALOGPS
logP-7.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity65.15 m³·mol⁻¹ChemAxon
Polarizability22.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dl-9700000000-76e306d0df20cdf2383dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ff0-9851000000-e9d6504a39fd334e4b9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0910000000-120b9ce241c6f49b2ac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-27173a0a79897e2f7ac9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2l-9600000000-912689a68e2339f3eb51Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022613
KNApSAcK IDNot Available
Chemspider ID388565
KEGG Compound IDC01259
BioCyc IDNot Available
BiGG ID37211
Wikipedia LinkNot Available
METLIN ID6234
PubChem Compound439460
PDB IDNot Available
ChEBI ID15786
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van Vlies N, Wanders RJ, Vaz FM: Measurement of carnitine biosynthesis enzyme activities by tandem mass spectrometry: differences between the mouse and the rat. Anal Biochem. 2006 Jul 1;354(1):132-9. Epub 2006 May 2. [PubMed:16707092 ]

Enzymes

General function:
Involved in oxidation reduction
Specific function:
Converts trimethyllysine (TML) into hydroxytrimethyllysine (HTML).
Gene Name:
TMLHE
Uniprot ID:
Q9NVH6
Molecular weight:
44048.895
Reactions
N6,N6,N6-Trimethyl-L-lysine + Oxoglutaric acid + Oxygen → 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine + Succinic acid + Carbon dioxidedetails