Showing metabocard for Dihydrolipoamide (BMDB0000985)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:29 UTC
Update Date2020-05-21 16:28:44 UTC
BMDB IDBMDB0000985
Secondary Accession Numbers
  • BMDB00985
Metabolite Identification
Common NameDihydrolipoamide
DescriptionDihydrolipoamide 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, dihydrolipoamide is considered to be a fatty amide lipid molecule. Dihydrolipoamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydrolipoamide exists in all living species, ranging from bacteria to humans. Dihydrolipoamide participates in a number of enzymatic reactions, within cattle. In particular, Dihydrolipoamide can be converted into lipoamide; which is catalyzed by the enzyme dihydrolipoyl dehydrogenase E3. In addition, Dihydrolipoamide can be biosynthesized from S-(3-methylbutanoyl)-dihydrolipoamide-e; which is mediated by the enzyme lipoamide acyltransferase component OF branched-chain alpha-keto acid dehydrogenase complex, mitochondrial. In cattle, dihydrolipoamide is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6,8-DimercaptooctanamideChEBI
DihydrothioctamideChEBI
6,8-Bis-sulfanyloctanamideHMDB
6,8-Dimercapto-octanamideHMDB
6,8-DisulfanyloctanamideHMDB
Dihydrolipoamide, (+-)-isomerHMDB
Chemical FormulaC8H17NOS2
Average Molecular Weight207.357
Monoisotopic Molecular Weight207.075155551
IUPAC Name6,8-disulfanyloctanimidic acid
Traditional Namedihydrothioctamide
CAS Registry Number3884-47-7
SMILES
OC(=N)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
InChI KeyVLYUGYAKYZETRF-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
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.22ALOGPS
logP1.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.68ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area44.08 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.7 m³·mol⁻¹ChemAxon
Polarizability23.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000985
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022352
KNApSAcK IDNot Available
Chemspider ID643
KEGG Compound IDC00579
BioCyc IDNot Available
BiGG ID35406
Wikipedia LinkDihydrolipoamide
METLIN ID5920
PubChem Compound663
PDB IDNot Available
ChEBI ID17694
References
Synthesis ReferenceWeitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Pyruvate dehydrogenase protein X component
General function:
Energy production and conversion
Specific function:
Required for anchoring dihydrolipoamide dehydrogenase (E3) to the dihydrolipoamide transacetylase (E2) core of the pyruvate dehydrogenase complexes of eukaryotes. This specific binding is essential for a functional PDH complex.
Gene Name:
PDHX
Uniprot ID:
P22439
Molecular weight:
53886.0
Reactions
S-Acetyldihydrolipoamide-E + Coenzyme A → Dihydrolipoamide + Acetyl-CoAdetails
Enzyme Details
2. 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-(3-Methylbutanoyl)-dihydrolipoamide-E + Coenzyme A → Isovaleryl-CoA + Dihydrolipoamidedetails
S-(2-Methylpropionyl)-dihydrolipoamide-E + Coenzyme A → Isobutyryl-CoA + Dihydrolipoamidedetails