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Showing metabocard for S-(2-Methylpropionyl)-dihydrolipoamide-E (HMDB0006868)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:15:34 UTC
Update Date2020-02-26 21:26:51 UTC
HMDB IDHMDB0006868
Secondary Accession Numbers
  • HMDB06868
Metabolite Identification
Common NameS-(2-Methylpropionyl)-dihydrolipoamide-E
DescriptionS-(2-Methylpropionyl)-dihydrolipoamide-E is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15977). It is the second to last step in the synthesis of branched chain fatty acid and is converted from 2-methyl-1-hydroxypropyl-ThPP via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to isobutyryl-CoA via the enzyme dihydrolipoyllysine-residue (2-methylpropanoyl)transferase [EC:2.3.1.168].
Structure
Data?1582752411
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9430000000-898ad5ac7f8d34382fceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0200-1590000000-256cf1b407c15039646aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-7960000000-68678b3f077aeb471401Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9600000000-b142c6b121e61d161a14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-062c-3590000000-dd8c6dd74f1ee11d43e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0axu-6790000000-b1e8d0173e84691b6bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-ec64c5922fd146f463b0Spectrum
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 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
Food Biomarker OntologyNot Available
VMH ID2MPDHL
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
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
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
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
Enzyme Details
3. Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial
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