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Showing Compound S-Acetyldihydrolipoamide (FDB022671)

Record Information
Version1.0
Creation date2011-09-21 00:17:43 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022671
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). [HMDB]. S-Acetyldihydrolipoamide is found in many foods, some of which are burdock, wax apple, atlantic herring, and cloudberry.
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
6-S-AcetyldihydrolipoamideChEBI
6-Acetylsulfanyl-8-sulfanyl-octanamideHMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioateHMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acidHMDB
6-acetylsulfanyl-8-sulfanyl-octanamidehmdb
S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioatehmdb
S-[6-amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acidhmdb
S-acetyldihydrolipoamidehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP2.46ALOGPS
logP1.24ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.16 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.23 m³·mol⁻¹ChemAxon
Polarizability27.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H19NO2S2
IUPAC name6-(acetylsulfanyl)-8-sulfanyloctanamide
InChI IdentifierInChI=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
Isomeric SMILESCC(=O)SC(CCS)CCCCC(N)=O
Average Molecular Weight249.393
Monoisotopic Molecular Weight249.085720237
Classification
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
  • Carboxamide group
  • Primary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Alkylthiol
  • Carboxylic acid derivative
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Acetyldihydrolipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9310000000-0f17192770cd2eed81e2Spectrum
Predicted GC-MSS-Acetyldihydrolipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-0390000000-f4f7a106ce708d65c83c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5590000000-4df718aaa87a6fbbd7952015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-4900000000-d4adb6f2a43bf9e5b1b92015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-2290000000-229a9fb285c737cc2c9f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-6590000000-6678ae77fcef8223dec92015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5de0a80883e527f54fbb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0490000000-9d67c94cbf8b72b1f3122021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01x0-1940000000-dafc5697832c093d72242021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tf-9600000000-853bdf0beb7957a18af32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1390000000-2259a6df55463871f9882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5950000000-5706c02348bf4fe9bb552021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9200000000-a65938d00822602054fb2021-09-24View Spectrum
NMRNot Available
ChemSpider ID1046
ChEMBL IDNot Available
KEGG Compound IDC01136
Pubchem Compound ID1076
Pubchem Substance IDNot Available
ChEBI ID16807
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01526
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference