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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:12:07 UTC
Update Date2021-09-14 14:57:29 UTC
HMDB IDHMDB0006867
Secondary Accession Numbers
  • HMDB06867
Metabolite Identification
Common 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].
Structure
Data?1582752411
Synonyms
ValueSource
S-(3-Methylbutanoyl)-dihydrolipoamideChEBI
S-(3-Methylbutanoyl)dihydrolipoyllysineHMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]HMDB
Chemical FormulaC13H25NO2S2
Average Molecular Weight291.473
Monoisotopic Molecular Weight291.132670429
IUPAC Name8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide
Traditional Name8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide
CAS Registry NumberNot Available
SMILES
CC(C)CC(=O)SCCC(S)CCCCC(N)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect

Adverse health effect

Disposition

Source

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 Solubility0.011 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.41631661259
DarkChem[M-H]-164.34131661259
DeepCCS[M+H]+168.61230932474
DeepCCS[M-H]-165.94930932474
DeepCCS[M-2H]-201.33330932474
DeepCCS[M+Na]+177.42730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
S-(3-Methylbutanoyl)-dihydrolipoamide-ECC(C)CC(=O)SCCC(S)CCCCC(N)=O3487.3Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-ECC(C)CC(=O)SCCC(S)CCCCC(N)=O2122.8Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-ECC(C)CC(=O)SCCC(S)CCCCC(N)=O2447.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C2485.6Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C2351.7Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C3712.1Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C2483.7Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C2326.4Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C3110.8Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2537.2Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2537.6Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C2974.5Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2514.9Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2441.3Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C3045.0Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2602.4Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2632.4Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C2757.1Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C2741.3Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C2584.2Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C3682.0Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C2714.7Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C2536.5Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C3179.9Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C3035.3Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2908.1Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C3058.4Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2996.7Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2826.7Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3168.7Standard polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1CC(C)CC(=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)C3325.8Semi standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1CC(C)CC(=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)C3146.4Standard non polar33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1CC(C)CC(=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)C3002.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9330000000-7645e890a76a3a0612542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-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-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Positive-QTOFsplash10-0adl-1590000000-73c597c9ff41eaa096da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Positive-QTOFsplash10-05bo-9860000000-959ec4437326b233f8c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Positive-QTOFsplash10-0r03-8900000000-a1e7f4573030a9fe253d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Negative-QTOFsplash10-0abc-3290000000-451e0e77862833c4f8a02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Negative-QTOFsplash10-05al-9460000000-643c13495fbd0a3ab1fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Negative-QTOFsplash10-000x-9100000000-be2cd4708826cfbabdff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Negative-QTOFsplash10-0006-0090000000-d3adc271f810363a2afc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Negative-QTOFsplash10-0avi-3960000000-19b3ed40b330088672342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Negative-QTOFsplash10-0006-9000000000-179d1961f85de3e540222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Positive-QTOFsplash10-052f-0290000000-2ee95e606494ba3b1dc02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Positive-QTOFsplash10-05ai-2790000000-dd330a5aa1d579c5bdd52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Positive-QTOFsplash10-000i-9500000000-dae67f00fee8e6329c5f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB024123
KNApSAcK IDNot Available
Chemspider ID389466
KEGG Compound IDC05119
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440566
PDB IDNot Available
ChEBI ID27462
Food Biomarker OntologyNot Available
VMH IDHC01377
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 branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58
General function:
Involved in acyltransferase activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
DBT
Uniprot ID:
P11182
Molecular weight:
53486.635