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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 17:04:10 UTC
Update Date2021-09-14 15:47:32 UTC
HMDB IDHMDB0006878
Secondary Accession Numbers
  • HMDB06878
Metabolite Identification
Common NameS-Acetyldihydrolipoamide-E
DescriptionS-Acetyldihydrolipoamide-E 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, S-acetyldihydrolipoamide-e is considered to be a fatty amide. Based on a literature review very few articles have been published on S-Acetyldihydrolipoamide-E.
Structure
Data?1582752412
Synonyms
ValueSource
8-S-AcetyldihydrolipoamideChEBI
Dihydrolipoyllysine-residue acetyltransferase]S-acetyldihydrolipoyllysineHMDB
Chemical FormulaC10H19NO2S2
Average Molecular Weight249.393
Monoisotopic Molecular Weight249.085720237
IUPAC Name8-(acetylsulfanyl)-6-sulfanyloctanamide
Traditional Name8-S-acetyldihydrolipoamide
CAS Registry NumberNot Available
SMILES
CC(=O)SCCC(S)CCCCC(N)=O
InChI Identifier
InChI=1S/C10H19NO2S2/c1-8(12)15-7-6-9(14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)
InChI KeyWXCOTNFMLYTGPZ-UHFFFAOYSA-N
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
  • 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
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.035 g/LALOGPS
logP10(2.49) g/LALOGPS
logP10(1.24) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)10.06ChemAxon
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
Polarizability27.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.37431661259
DarkChem[M-H]-153.30131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
S-Acetyldihydrolipoamide-ECC(=O)SCCC(S)CCCCC(N)=O3305.9Standard polar33892256
S-Acetyldihydrolipoamide-ECC(=O)SCCC(S)CCCCC(N)=O1944.5Standard non polar33892256
S-Acetyldihydrolipoamide-ECC(=O)SCCC(S)CCCCC(N)=O2256.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
S-Acetyldihydrolipoamide-E,1TMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C2263.6Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,1TMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C2177.4Standard non polar33892256
S-Acetyldihydrolipoamide-E,1TMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C3555.2Standard polar33892256
S-Acetyldihydrolipoamide-E,1TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C2241.1Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,1TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C2121.0Standard non polar33892256
S-Acetyldihydrolipoamide-E,1TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C2964.4Standard polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2345.6Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2351.5Standard non polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2871.1Standard polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2307.3Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2239.3Standard non polar33892256
S-Acetyldihydrolipoamide-E,2TMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2896.2Standard polar33892256
S-Acetyldihydrolipoamide-E,3TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2442.1Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,3TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2448.2Standard non polar33892256
S-Acetyldihydrolipoamide-E,3TMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2635.3Standard polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C2516.0Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C2416.6Standard non polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #1CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C3541.4Standard polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C2477.7Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C2340.0Standard non polar33892256
S-Acetyldihydrolipoamide-E,1TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C3038.3Standard polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2837.7Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2735.8Standard non polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2916.1Standard polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2796.6Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2646.9Standard non polar33892256
S-Acetyldihydrolipoamide-E,2TBDMS,isomer #2CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2992.7Standard polar33892256
S-Acetyldihydrolipoamide-E,3TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C3151.8Semi standard non polar33892256
S-Acetyldihydrolipoamide-E,3TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2995.9Standard non polar33892256
S-Acetyldihydrolipoamide-E,3TBDMS,isomer #1CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2860.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - S-Acetyldihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9520000000-69d3dd2c0fb35a09a40e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Acetyldihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Acetyldihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 10V, Positive-QTOFsplash10-0l3r-2390000000-505da9922f406629961e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 20V, Positive-QTOFsplash10-05cr-3970000000-cc3ec97184b82e8019472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 40V, Positive-QTOFsplash10-0kk9-9400000000-5a4de4b7148728d86afb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 10V, Negative-QTOFsplash10-074j-1490000000-752a8225d9d8c0f7b0152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 20V, Negative-QTOFsplash10-006x-9780000000-18b1e21830fcd3117bfd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 40V, Negative-QTOFsplash10-0006-9000000000-bc1ab1e0a03f30f870d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 10V, Positive-QTOFsplash10-0gb9-0490000000-2e23dadf862c86f5506a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 20V, Positive-QTOFsplash10-001i-5960000000-c4503c60da932f3770342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 40V, Positive-QTOFsplash10-0006-9200000000-4c9e81472727ea87088b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 10V, Negative-QTOFsplash10-0002-0090000000-3f52d189c9f520524a282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 20V, Negative-QTOFsplash10-00di-9560000000-fe21c84846a737aa792b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide-E 40V, Negative-QTOFsplash10-006x-9000000000-cf0fb5bec2c2b1c037bf2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024131
KNApSAcK IDNot Available
Chemspider ID21865772
KEGG Compound IDC16255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24906332
PDB IDNot Available
ChEBI ID50623
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
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:
PDHB
Uniprot ID:
P11177
Molecular weight:
39233.1
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 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:
PDHA2
Uniprot ID:
P29803
Molecular weight:
42932.855
General function:
Involved in acyltransferase activity
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:
DLAT
Uniprot ID:
P10515
Molecular weight:
68996.03
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular weight:
48179.59
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
DLAT
Uniprot ID:
Q86YI5
Molecular weight:
68996.0