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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:20:38 UTC
Update Date2021-09-14 15:43:42 UTC
HMDB IDHMDB0006869
Secondary Accession Numbers
  • HMDB06869
Metabolite Identification
Common NameS-(2-Methylbutanoyl)-dihydrolipoamide
DescriptionS-(2-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in isoleucine degradation. S-(2-Methylbutanoyl)-dihydrolipoamide is normally conjugated to a lysine residue of the methylpropanoyltransferase enzyme (E stands for enzyme). The structure shown here is the free form. Specifically S-(2-Methylbutanoyl)-dihydrolipoamide-E is the 2-methylbutanoyl thioester of the reduced lipoyllysine residue in dihydrolipoyllysine-residue (2-methylpropanoyl)transferase.
Structure
Data?1582752411
Synonyms
ValueSource
S-(2-Methylbutanoyl)dihydrolipoyllysineHMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]HMDB
Chemical FormulaC13H25NO2S2
Average Molecular Weight291.473
Monoisotopic Molecular Weight291.132670429
IUPAC Name8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide
Traditional Name8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide
CAS Registry NumberNot Available
SMILES
CCC(C)C(=O)SCCC(S)CCCCC(N)=O
InChI Identifier
InChI=1S/C13H25NO2S2/c1-3-10(2)13(16)18-9-8-11(17)6-4-5-7-12(14)15/h10-11,17H,3-9H2,1-2H3,(H2,14,15)
InChI KeyUFNCWFSSEGPJNL-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

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(3.67) g/LALOGPS
logP10(2.92) g/LChemAxon
logS10(-4.4) 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 Count11ChemAxon
Refractivity81.03 m³·mol⁻¹ChemAxon
Polarizability33.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.50831661259
DarkChem[M-H]-166.21631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9440000000-877a8908188a4b9ebf152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 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-(2-Methylbutanoyl)-dihydrolipoamide 10V, Positive-QTOFsplash10-05ox-1590000000-8990b01bec1542bc86852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Positive-QTOFsplash10-0a70-6950000000-ec727734be57f42cd4292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Positive-QTOFsplash10-0a4i-9600000000-66cf65ecaa53c1f3c2822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Negative-QTOFsplash10-0ab9-4590000000-2a509e71418cfb3b64992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Negative-QTOFsplash10-0ac3-9680000000-907d9cdccee37b33c93c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Negative-QTOFsplash10-0006-9100000000-c6f4b7f06ed0787622762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Positive-QTOFsplash10-0006-0190000000-64102de5dbea75355e972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Positive-QTOFsplash10-00a6-2940000000-98da17f6a6690d13a7872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Positive-QTOFsplash10-059i-9400000000-370f86855cf150dcc7982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Negative-QTOFsplash10-0006-0090000000-431d68145b7602d0fba02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Negative-QTOFsplash10-0avi-1940000000-95224a4cc03836a7327f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Negative-QTOFsplash10-0006-9100000000-bf3e84c89d49f43b87612021-09-22Wishart 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 IDFDB024125
KNApSAcK IDNot Available
Chemspider ID389465
KEGG Compound IDC05118
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440565
PDB IDNot Available
ChEBI ID28692
Food Biomarker OntologyNot Available
VMH IDHC01376
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