We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Metabolome Database



Showing metabocard for S-Acetyldihydrolipoamide (BMDB01526)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:53
Accession Number BMDB01526
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).
Synonyms
  1. 6-S-Acetyldihydrolipoamide
  2. 6-acetylsulfanyl-8-sulfanyl-octanamide
  3. S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate
  4. S-acetyldihydrolipoamide
  5. S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid
Chemical IUPAC Name S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate
Chemical Formula C10H19NO2S2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Lipoamides and Derivatives
Sub Class
  • Miscellaneous lipoamides
Family
  • Mammalian_Metabolite
Species
  • primary carboxylic acid amide; thiocarboxylic acid ester; thiol (sulfanyl compound); alkylthiol
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 249.393
Monoisotopic Molecular Weight 249.085724
Isomeric SMILES CC(=O)SC(CCS)CCCCC(N)=O
Canonical SMILES CC(=O)SC(CCS)CCCCC(N)=O
KEGG Compound ID C01136 Link Image
BioCyc ID S-ACETYLDIHYDROLIPOAMIDE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 6299 Link Image
PubChem Compound 1076 Link Image
PubChem Substance 3152 Link Image
ChEBI ID 16807 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0355 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.46 [Predicted by ALOGPS]; 1.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Alanine and aspartate metabolism
  • Pyruvate Metabolism
HMDB Pathways
Name Alanine and aspartate metabolism
Image Show Link Image
Name Pyruvate Metabolism
Image Show Link Image
KEGG Pathways
Name Alanine and aspartate metabolism
Image Show Link Image
Name Pyruvate Metabolism
Image Show Link Image
SimCell Pathways
Name Alanine and aspartate metabolism
Image Show Link Image
Graph Show Link Image
SBML Download (XML) Link Image
Name Pyruvate Metabolism
Image Show Link Image
Graph
SBML
General References Not Available