Human Metabolome Database Version 3.5

Showing metabocard for S-Acetyldihydrolipoamide (HMDB01526)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:43 -0700
HMDB ID HMDB01526
Secondary Accession Numbers
  • HMDB06951
Metabolite Identification
Common Name S-Acetyldihydrolipoamide
Description S-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H19NO2S2
Average Molecular Weight 249.393
Monoisotopic Molecular Weight 249.085720237
IUPAC Name 6-(acetylsulfanyl)-8-sulfanyloctanamide
Traditional IUPAC Name 6-(acetylsulfanyl)-8-sulfanyloctanamide
CAS Registry Number Not 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 Key ARGXEXVCHMNAQU-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Dithiolanes
Sub Class Lipoamides
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 Parent Lipoamides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.035 g/L ALOGPS
LogP 2.46 ALOGPS
LogP 1.24 ChemAxon
LogS -3.85 ALOGPS
pKa (strongest acidic) 10.19 ChemAxon
pKa (strongest basic) -0.58 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 60.16 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 67.23 ChemAxon
Polarizability 27.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022671
KNApSAcK ID Not Available
Chemspider ID 1046 Link_out
KEGG Compound ID C01136 Link_out
BioCyc ID S-ACETYLDIHYDROLIPOAMIDE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01526 Link_out
Metagene Link HMDB01526 Link_out
METLIN ID 6299 Link_out
PubChem Compound 1076 Link_out
PDB ID Not Available
ChEBI ID 16807 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
Reactions: Not Available
Gene Name: PDHA1
Uniprot ID: P08559 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dihydrolipoamide S-acetyltransferase
Reactions: Not Available
Gene Name: DLAT
Uniprot ID: Q86YI5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA