Record Information
Version1.0
Creation date2011-09-21 00:12:27 UTC
Update date2019-11-26 03:21:02 UTC
Primary IDFDB022340
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLipoamide
DescriptionLipoamide is the oxidized form of glutathione. (PMID:8957191) Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2). [HMDB]. Lipoamide is found in many foods, some of which are pepper (c. frutescens), black crowberry, common salsify, and wild leek.
CAS Number940-69-2
Structure
Thumb
Synonyms
SynonymSource
1,2-Dithiolane-3-pentanamideChEBI
alpha-Lipoic acid amideChEBI
LipoacinChEBI
ThioctamideChEBI
Thioctic acid amideChEBI
Vitamin NChEBI
a-Lipoate amideGenerator
a-Lipoic acid amideGenerator
alpha-Lipoate amideGenerator
Α-lipoate amideGenerator
Α-lipoic acid amideGenerator
Thioctate amideGenerator
5-(1,2-Dithiolan-3-yl)-pentanamideHMDB
5-(1,2-Dithiolan-3-yl)pentanamideHMDB
5-(1,2-Dithiolan-3-yl)valeramideHMDB
5-(Dithiolan-3-yl)valeramideHMDB
alpha-LipoateHMDB
alpha-Lipoic acidHMDB
DL-6-Thioctic amideHMDB
DL-LipoamideHMDB
LipamideHMDB
LipoamidHMDB
LipoicinHMDB
LipozymeHMDB
LypoaranHMDB
PathoclonHMDB
ThioamiHMDB
ThioctamidHMDB
ThiotominHMDB
TicolinHMDB
1,2-Dithiolane-3-valeramideHMDB
6,8-Thioctic amideHMDB
alpha-Lipoic amideHMDB
Lipoamide, (+-)-isomerHMDB
5-(1,2-dithiolan-3-yl)-pentanamidehmdb
5-(1,2-dithiolan-3-yl)pentanamidehmdb
Alpha-lipoic acid amidehmdb
dl-6-Thioctic amidehmdb
DL-lipoamidehmdb
Thioctic acid amide (jan)hmdb
Vitamin nhmdb
α-lipoate amideGenerator
α-lipoic acid amideGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.3ALOGPS
logP1.31ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.19 m³·mol⁻¹ChemAxon
Polarizability22.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H15NOS2
IUPAC name5-(1,2-dithiolan-3-yl)pentanamide
InChI IdentifierInChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
InChI KeyFCCDDURTIIUXBY-UHFFFAOYSA-N
Isomeric SMILESNC(=O)CCCCC1CCSS1
Average Molecular Weight205.341
Monoisotopic Molecular Weight205.059505487
Classification
Description Belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoamides
Direct ParentLipoamides
Alternative Parents
Substituents
  • Lipoamide
  • Fatty amide
  • Fatty acyl
  • 1,2-dithiolane
  • Carboxamide group
  • Organic disulfide
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSLipoamide, 2 TMS, GC-MS Spectrumsplash10-014i-6963000000-7e1887d53c2801b09961Spectrum
GC-MSLipoamide, 1 TMS, GC-MS Spectrumsplash10-017l-3920000000-a3a7a08acf06d41c9b73Spectrum
GC-MSLipoamide, non-derivatized, GC-MS Spectrumsplash10-014i-6963000000-7e1887d53c2801b09961Spectrum
GC-MSLipoamide, non-derivatized, GC-MS Spectrumsplash10-017l-3920000000-a3a7a08acf06d41c9b73Spectrum
GC-MSLipoamide, non-derivatized, GC-MS Spectrumsplash10-014i-1910000000-b6ee336856e354af8114Spectrum
GC-MSLipoamide, non-derivatized, GC-MS Spectrumsplash10-00di-3900000000-60cad9dd198c3ad64ed7Spectrum
Predicted GC-MSLipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f96-9800000000-ac967ad86beefc26c983Spectrum
Predicted GC-MSLipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-24fca44fc025dbd6be18Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ziu-9700000000-7dfd23f450bdfd581100Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056u-9000000000-13583c4eb6b06a56c392Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-052r-2920000000-a4fb7176abf63e581f5eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-2900000000-10a079a84f024494ae23Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udl-9400000000-7a03c741edae36dff9cfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-50512172ce038bce2995Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-7652a33c17a37b6914aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-0df59a6540bede8a4a79Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-2920000000-a4fb7176abf63e581f5eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-158c946037c5d7bb3e50Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udl-9400000000-7a03c741edae36dff9cfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-fa779b1c88469a732321Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1900000000-9e4b6873b24c66cf9f69Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0900000000-b37ce6b25b9feef09b96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0940000000-d79e1aa52057e567d71fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3900000000-abd8148048c5f282d889Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adr-9500000000-9769c619660ab6af46d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zml-1920000000-79d57d488cb8fbc804a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdo-4910000000-d264eaf6e242c36bc563Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-289d2f20046f7819a7caSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID840
ChEMBL IDCHEMBL1403899
KEGG Compound IDC00248
Pubchem Compound ID863
Pubchem Substance IDNot Available
ChEBI ID17460
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00962
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34384
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLipoamide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine dehydrogenase [decarboxylating], mitochondrialGLDCP23378
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference