Showing metabocard for Lipoyllysine (BMDB0095991)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-10 16:59:25 UTC
Update Date2020-04-22 18:55:22 UTC
BMDB IDBMDB0095991
Secondary Accession Numbers
  • BMDB95991
Metabolite Identification
Common NameLipoyllysine
DescriptionLipoyllysine belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Based on a literature review very few articles have been published on Lipoyllysine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
DL-Lipoyl-L-lysineHMDB
Lipoyl-N-epsilon-lysineHMDB
mono-1,2-Dithiolane-3-pentanoateHMDB
mono-1,2-Dithiolane-3-pentanoate-L-lysineHMDB
mono-1,2-Dithiolane-3-pentanoic acidHMDB
(2R)-2-Amino-6-{[5-(1,2-dithiolan-3-yl)-1-hydroxypentylidene]amino}hexanoateGenerator
LipoyllysineMeSH
Chemical FormulaC14H26N2O3S2
Average Molecular Weight334.498
Monoisotopic Molecular Weight334.138484088
IUPAC Name(2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid
Traditional Name(2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid
CAS Registry NumberNot Available
SMILES
N[C@H](CCCCNC(=O)CCCCC1CCSS1)C(O)=O
InChI Identifier
InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)/t11?,12-/m1/s1
InChI KeyCOTIXRRJLCSLLS-PIJUOVFKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoamides
Direct ParentLipoamides
Alternative Parents
Substituents
  • Lipoamide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • 1,2-dithiolane
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organic disulfide
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.02ALOGPS
logP-0.82ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity88.98 m³·mol⁻¹ChemAxon
Polarizability36.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012996
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029239
KNApSAcK IDNot Available
Chemspider ID35032557
KEGG Compound IDNot Available
BioCyc IDProtein-6-N-lipoyl-lysine
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481572
PDB IDNot Available
ChEBI ID175262
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available