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(S)-Succinyldihydrolipoamide (M2MDB004121)

Record Information
Version2.0
Creation Date2012-11-06 04:55:28 -0700
Update Date2015-06-03 17:27:29 -0600
Secondary Accession Numbers
  • ECMDB23731
Identification
Name:(S)-Succinyldihydrolipoamide
Description(S)-Succinyldihydrolipoamide is a metabolite (a product as well as a substrate) in glutamate degradation. It is also invovled in citrate cycle and is a reactant for oxoglutarate dehydrogenase (EC 1.2.4.2) and dihydrolipoyllysine-residue succinyltransferase (EC 2.3.1.61).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 4-[(3R)-8-amino-8-oxo-1-Sulfanyloctan-3-yl]sulfanyl-4-oxobutanoate
  • 4-[(3R)-8-amino-8-oxo-1-sulfanyloctan-3-yl]sulfanyl-4-oxobutanoic acid
  • 4-[(3R)-8-amino-8-oxo-1-Sulphanyloctan-3-yl]sulphanyl-4-oxobutanoate
  • 4-[(3R)-8-amino-8-oxo-1-Sulphanyloctan-3-yl]sulphanyl-4-oxobutanoic acid
  • S-succinyl-dihydrolipoamide
  • S-Succinyldihydrolipoamide
Chemical Formula:C12H21NO4S2
Weight:Average: 307.429
Monoisotopic: 307.091199545
InChI Key:RJCJWONCSKSHES-SECBINFHSA-N
InChI:InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(7-8-18)19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)/t9-/m1/s1
CAS number:Not Available
IUPAC Name:4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid
Traditional IUPAC Name:4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid
SMILES:NC(=O)CCCC[C@H](CCS)SC(=O)CCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Thia fatty acid
  • Fatty acyl thioester
  • Fatty amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Alkylthiol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP1.97ALOGPS
logP1.06ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity78.12 m³·mol⁻¹ChemAxon
Polarizability32.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Succinyl-CoA + Dihydrolipoamide + Succinyl-CoA + Dihydrolipoamide > Coenzyme A + (S)-Succinyldihydrolipoamide
SMPDB Pathways:
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ukc-9880000000-d66345c90ce5eb67fa60View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9533000000-a1ebe0f3e16866573001View 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, Positivesplash10-0596-0190000000-b49046dab0850898c889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-2190000000-474bcff100b398100e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nt9-4910000000-247a7886ecdb5a884d7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0596-0190000000-b49046dab0850898c889View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-2190000000-474bcff100b398100e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0nt9-4910000000-247a7886ecdb5a884d7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5294000000-672a48ef8e666cb0ee5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9360000000-f9e4f05adcb51d48447cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9100000000-d7f410ba584f3aad89ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1229000000-d6ef878a291e343f754aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7970000000-eff246297f1390d8e037View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9500000000-66fb2d1c65f8ee705da4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0369000000-035798c3620974bb7aabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1910000000-e3af53d75b9037036cfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-5900000000-f70f4c6e3a3b250e485fView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17432
HMDB IDHMDB01177
Pubchem Compound ID439425
Kegg IDC01169
ChemSpider ID388536
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). It contains multiple copies of three enzymatic components:pyruvate dehydrogenase (E1), dihydrolipoamide acetyltransferase (E2) and lipoamide dehydrogenase (E3)
Gene Name:
aceF
Uniprot ID:
P06959
Molecular weight:
66096
Reactions
Acetyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine = CoA + enzyme N(6)-(S-acetyldihydrolipoyl)lysine.