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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:43 UTC
HMDB IDHMDB01526
Secondary Accession Numbers
  • HMDB06951
Metabolite Identification
Common NameS-Acetyldihydrolipoamide
DescriptionS-Acetyldihydrolipoamide is a thio-acetylated form of dihydrolipoamide. The molecule is commonly conjugated to lysine residues. The structure shown is the free form of the molecule. Pyruvate dehydrogenase complex. The reaction is 2-(alpha-hydroxyethyl)-TPP + lipoamide => S-acetyldihydrolipoamide + TPP [Homo sapiens], occuring in mitochondrial matrix. (reactome.org). S-Acetyldihydrolipoamide is an intermediate in alanine, aspartate and pyruvate metabolism and glycolysis/gluconeogenesis (KEGG:C01136). It is converted from 2-hydroxyethyl-THPP and lipoamide via the enzyme pyruvate dehydrogenase (EC:1.2.4.1). It is then converted to acetyl-CoA via the enzyme pyruvate dehydrogenase E2 component (dihydrolipoamide acetyltransferase) (EC:2.3.1.12).
Structure
Thumb
Synonyms
  1. 6-Acetylsulfanyl-8-sulfanyl-octanamide
  2. 6-S-Acetyldihydrolipoamide
  3. S-Acetyldihydrolipoamide
  4. S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate
  5. S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid
Chemical FormulaC10H19NO2S2
Average Molecular Weight249.393
Monoisotopic Molecular Weight249.085720237
IUPAC Name6-(acetylsulfanyl)-8-sulfanyloctanamide
Traditional IUPAC Name6-(acetylsulfanyl)-8-sulfanyloctanamide
CAS Registry NumberNot Available
SMILES
CC(=O)SC(CCS)CCCCC(N)=O
InChI Identifier
InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)
InChI KeyARGXEXVCHMNAQU-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassDithiolanes
Sub ClassLipoamides
Other Descriptors
  • Aliphatic Acyclic Compounds
  • N-acyl Amines
  • S-substituted dihydrolipoamide(ChEBI)
  • a small molecule(Cyc)
Substituents
  • Alkylthiol
  • Carboxamide Group
  • Carboxylic Thioester
  • Primary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
  • Thiol (Sulfanyl Compound)
Direct ParentLipoamides
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 solubility0.035 g/LALOGPS
logP2.46ALOGPS
logP1.24ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)10.19ChemAxon
pKa (strongest basic)-0.58ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area60.16ChemAxon
rotatable bond count9ChemAxon
refractivity67.23ChemAxon
polarizability27.66ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022671
KNApSAcK IDNot Available
Chemspider ID1046
KEGG Compound IDC01136
BioCyc IDS-ACETYLDIHYDROLIPOAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01526
Metagene LinkHMDB01526
METLIN ID6299
PubChem Compound1076
PDB IDNot Available
ChEBI ID16807
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yang YS, Frey PA: Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide. Biochemistry. 1986 Dec 16;25(25):8173-8. Pubmed: 3101735
  2. Butterworth PJ, Tsai CS, Eley MH, Roche TE, Reed LJ: A kinetic study of dihydrolipoyl transacetylase from bovine kidney. J Biol Chem. 1975 Mar 10;250(5):1921-5. Pubmed: 1089667
  3. O'Connor TP, Roche TE, Paukstelis JV: 13C nuclear magnetic resonance study of the pyruvate dehydrogenase-catalyzed acetylation of dihydrolipoamide. J Biol Chem. 1982 Mar 25;257(6):3110-2. Pubmed: 6801041

Enzymes

General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
P08559
Molecular weight:
43295.255
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
DLAT
Uniprot ID:
Q86YI5
Molecular weight:
68996.0