Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB004121
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
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
Average Molecular Weight: 307.429
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Thia fatty acids
Alternative Parents
Substituents
  • Fatty acyl thioester
  • Thia fatty acid
  • Fatty amide
  • Thiocarboxylic acid ester
  • Primary carboxylic acid amide
  • Carboxamide group
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity78.12 m3·mol-1ChemAxon
Polarizability32.86 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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