Showing metabocard for S-(2-Methylpropionyl)-dihydrolipoamide-E (BMDB0006868)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:58 UTC
Update Date2020-05-21 16:28:45 UTC
BMDB IDBMDB0006868
Secondary Accession Numbers
  • BMDB06868
Metabolite Identification
Common NameS-(2-Methylpropionyl)-dihydrolipoamide-E
DescriptionS-(2-Methylpropionyl)-dihydrolipoamide-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-(2-methylpropionyl)-dihydrolipoamide-e-e is considered to be a fatty amide lipid molecule. S-(2-Methylpropionyl)-dihydrolipoamide-e is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. S-(2-Methylpropionyl)-dihydrolipoamide-e participates in a number of enzymatic reactions, within cattle. In particular, S-(2-Methylpropionyl)-dihydrolipoamide-e can be biosynthesized from 2-methyl-1-hydroxypropyl-THPP through the action of the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In addition, S-(2-Methylpropionyl)-dihydrolipoamide-e can be biosynthesized from lipoamide through the action of the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In cattle, S-(2-methylpropionyl)-dihydrolipoamide-e-e is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
S-(2-Methylpropanoyl)-dihydrolipoamideChEBI
S-(2-Methylpropionyl)-dihydrolipoamideChEBI
S-(2-Methylpropanoyl)-dihydrolipoamide-eHMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]S-(2-methylpropanoyl)dihydrolipoyllysineHMDB
Chemical FormulaC12H23NO2S2
Average Molecular Weight277.447
Monoisotopic Molecular Weight277.117020365
IUPAC Name8-[(2-methylpropanoyl)sulfanyl]-6-sulfanyloctanamide
Traditional Name8-[(2-methylpropanoyl)sulfanyl]-6-sulfanyloctanamide
CAS Registry NumberNot Available
SMILES
CC(C)C(=O)SCCC(S)CCCCC(N)=O
InChI Identifier
InChI=1S/C12H23NO2S2/c1-9(2)12(15)17-8-7-10(16)5-3-4-6-11(13)14/h9-10,16H,3-8H2,1-2H3,(H2,13,14)
InChI KeyUEFURMXXHJCLJP-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.05ALOGPS
logP2.48ChemAxon
logS-4.2ALOGPS
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 Count10ChemAxon
Refractivity76.43 m³·mol⁻¹ChemAxon
Polarizability32.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9430000000-898ad5ac7f8d34382fceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0200-1590000000-256cf1b407c15039646aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-7960000000-68678b3f077aeb471401View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9600000000-b142c6b121e61d161a14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-062c-3590000000-dd8c6dd74f1ee11d43e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0axu-6790000000-b1e8d0173e84691b6bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-ec64c5922fd146f463b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-7ce7db6d296a0c9ccd1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044l-3950000000-408139b7c147c5ffb59bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007d-9400000000-69ca2ae5bb862cef6bafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-8ed120c1f1da33069a71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmi-2940000000-f72c23450f1a5b08d40cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-daf484d53de0437afb9fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006868
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024124
KNApSAcK IDNot Available
Chemspider ID10128135
KEGG Compound IDC04424
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11953835
PDB IDNot Available
ChEBI ID17577
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Energy production and conversion
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:
P11178
Molecular weight:
51678.0
Reactions
2-Methyl-1-hydroxypropyl-ThPP → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Lipoamide → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Energy production and conversion
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:
P21839
Molecular weight:
42935.0
Reactions
2-Methyl-1-hydroxypropyl-ThPP → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Lipoamide → S-(2-Methylpropionyl)-dihydrolipoamide-Edetails
Enzyme Details
3. Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial
General function:
Energy production and conversion
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). Within this complex, the catalytic function of this enzyme is to accept, and to transfer to coenzyme A, acyl groups that are generated by the branched-chain alpha-keto acid decarboxylase component.
Gene Name:
DBT
Uniprot ID:
P11181
Molecular weight:
53410.0
Reactions
S-(2-Methylpropionyl)-dihydrolipoamide-E + Coenzyme A → Isobutyryl-CoA + Dihydrolipoamidedetails