Record Information
Version1.0
Creation date2011-09-21 00:40:16 UTC
Update date2015-07-21 06:58:00 UTC
Primary IDFDB024123
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-(3-Methylbutanoyl)-dihydrolipoamide-E
DescriptionS-(3-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15975 ). It is the second to last step in the synthesis of branched chain fatty acid and is converted from 3-methyl-hydroxybutyl-ThPP via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to 3-methylbutanoyl-CoA via the enzyme dihydrolipoyllysine-residue (2-methylpropanoyl)transferase[EC:2.3.1.168]. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
S-(3-Methylbutanoyl)-dihydrolipoamideChEBI
S-(3-Methylbutanoyl)dihydrolipoyllysineHMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]HMDB
S-(3-Methylbutanoyl)-dihydrolipoamide-Ehmdb
S-(3-methylbutanoyl)dihydrolipoyllysinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.35ALOGPS
logP2.67ChemAxon
logS-4.4ALOGPS
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 Count11ChemAxon
Refractivity81 m³·mol⁻¹ChemAxon
Polarizability33.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H25NO2S2
IUPAC name8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide
InChI IdentifierInChI=1S/C13H25NO2S2/c1-10(2)9-13(16)18-8-7-11(17)5-3-4-6-12(14)15/h10-11,17H,3-9H2,1-2H3,(H2,14,15)
InChI KeyKMUSXGCRMMQDBP-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC(=O)SCCC(S)CCCCC(N)=O
Average Molecular Weight291.473
Monoisotopic Molecular Weight291.132670429
Classification
Description Belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentFatty acyl thioesters
Alternative Parents
Substituents
  • Fatty acyl thioester
  • Fatty amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Alkylthiol
  • Carboxylic acid derivative
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties - Experimental
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-(3-Methylbutanoyl)-dihydrolipoamide-E, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9330000000-7645e890a76a3a061254Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adl-1590000000-73c597c9ff41eaa096daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bo-9860000000-959ec4437326b233f8c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r03-8900000000-a1e7f4573030a9fe253dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-3290000000-451e0e77862833c4f8a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05al-9460000000-643c13495fbd0a3ab1fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9100000000-be2cd4708826cfbabdffSpectrum
NMRNot Available
ChemSpider ID389466
ChEMBL IDNot Available
KEGG Compound IDC05119
Pubchem Compound ID440566
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06867
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
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrialDBTP11182
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference