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Identification
YMDB IDYMDB00899
NameDihydrolipoamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDihydrolipoamide belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, dihydrolipoamide is considered to be a fatty amide lipid molecule. Dihydrolipoamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • 6,8-bis-sulfanyloctanamide
  • 6,8-dimercapto-Octanamide
  • 6,8-dimercaptooctanamide
  • 6,8-disulfanyloctanamide
  • dihydrolipoamide
  • Dihydrothioctamide
  • Dihydrolipoamide, (+-)-isomer
CAS number3884-47-7
WeightAverage: 207.357
Monoisotopic: 207.075155551
InChI KeyVLYUGYAKYZETRF-UHFFFAOYSA-N
InChIInChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
IUPAC Name6,8-disulfanyloctanimidic acid
Traditional IUPAC Namedihydrothioctamide
Chemical FormulaC8H17NOS2
SMILES[H]OC(=N[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(S[H])C([H])([H])C([H])([H])S[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentFatty amides
Alternative Parents
Substituents
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.099 g/LALOGPS
logP2.22ALOGPS
logP1.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.68ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area44.08 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.7 m³·mol⁻¹ChemAxon
Polarizability23.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NAD + DihydrolipoamideNADH + lipoamide + hydron
S(8)-aminomethyldihydrolipoamide + 5,6,7,8-Tetrahydrofolic acid5,10-Methylene-THF + Ammonium + Dihydrolipoamide
Coenzyme A + S(8)-succinyldihydrolipoamideDihydrolipoamide + Succinyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Niu, X. D., Browning, K. S., Behal, R. H., Reed, L. J. (1988). "Cloning and nucleotide sequence of the gene for dihydrolipoamide acetyltransferase from Saccharomyces cerevisiae." Proc Natl Acad Sci U S A 85:7546-7550.3050999
  • Ruttkay-Nedecky, B., Subik, J. (1990). "The OGD1 gene, affecting 2-oxoglutarate dehydrogenase in S. cerevisiae, is closely linked to HIS5 on chromosome IX." Curr Genet 17:85-88.2178788
Synthesis Reference:Weitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3.
External Links:
ResourceLink
CHEBI ID17694
HMDB IDHMDB00985
Pubchem Compound ID663
Kegg IDC00579
ChemSpider ID643
FOODB IDFDB022352
WikipediaDihydrolipoamide
BioCyc IDDIHYDROLIPOAMIDE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the alpha- ketoacid dehydrogenase complexes. This includes the pyruvate dehydrogenase complex, which catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). Acts also as component of the glycine cleavage system (glycine decarboxylase complex), which catalyzes the degradation of glycine
Gene Name:
LPD1
Uniprot ID:
P09624
Molecular weight:
54009.69922
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD(+) → protein N(6)-(lipoyl)lysine + NADH.