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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-21 17:57:28 UTC
HMDB IDHMDB0000962
Secondary Accession Numbers
  • HMDB00962
  • HMDB06877
  • HMDB06950
Metabolite Identification
Common NameLipoamide
DescriptionLipoamide 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. (Wikipedia). 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).
Structure
Thumb
Synonyms
ValueSource
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-valeramideMeSH
6,8-Thioctic amideMeSH
alpha-Lipoic amideMeSH
Lipoamide, (+-)-isomerMeSH
Chemical FormulaC8H15NOS2
Average Molecular Weight205.341
Monoisotopic Molecular Weight205.059505487
IUPAC Name5-(1,2-dithiolan-3-yl)pentanamide
Traditional Namelipoamide
CAS Registry Number940-69-2
SMILES
NC(=O)CCCCC1CCSS1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as lipoamides. These are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDithiolanes
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
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126.0 - 129.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 mg/mLALOGPS
logP2.3ALOGPS
logP1.31ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.19 m3·mol-1ChemAxon
Polarizability22.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-6963000000-7e1887d53c2801b09961View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017l-3920000000-a3a7a08acf06d41c9b73View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-MSsplash10-014i-6963000000-7e1887d53c2801b09961View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-017l-3920000000-a3a7a08acf06d41c9b73View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-1910000000-b6ee336856e354af8114View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-3900000000-60cad9dd198c3ad64ed7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-24fca44fc025dbd6be18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ziu-9700000000-7dfd23f450bdfd581100View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056u-9000000000-13583c4eb6b06a56c392View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-052r-2920000000-a4fb7176abf63e581f5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-2900000000-10a079a84f024494ae23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udl-9400000000-7a03c741edae36dff9cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-50512172ce038bce2995View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-7652a33c17a37b6914aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-0df59a6540bede8a4a79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-2920000000-a4fb7176abf63e581f5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-158c946037c5d7bb3e50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zfr-9800000000-b01332176d6829b1eaa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udl-9400000000-7a03c741edae36dff9cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9100000000-7b44dfbfcbb0cc516254View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-fa779b1c88469a732321View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1900000000-9e4b6873b24c66cf9f69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations
  • Saliva
Tissue Location
  • Placenta
Pathways
NameSMPDB/PathwhizKEGG
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyPw000061Pw000061 greyscalePw000061 simpleNot Available
2-aminoadipic 2-oxoadipic aciduriaPw000696Pw000696 greyscalePw000696 simpleNot Available
2-ketoglutarate dehydrogenase complex deficiencyPw000525Pw000525 greyscalePw000525 simpleNot Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyPw000063Pw000063 greyscalePw000063 simpleNot Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type IPw000065Pw000065 greyscalePw000065 simpleNot Available
Displaying entries 1 - 5 of 44 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.153 +/- 0.182 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.278 +/- 0.208 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.281 +/- 0.203 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.424 +/- 0.941 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.439 +/- 0.254 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.549 +/- 0.674 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022340
KNApSAcK IDNot Available
Chemspider ID840
KEGG Compound IDC00248
BioCyc IDLIPOAMIDE
BiGG ID34384
Wikipedia LinkLipoamide
NuGOwiki LinkHMDB0000962
METLIN ID3372
PubChem Compound863
PDB IDNot Available
ChEBI ID17460
References
Synthesis ReferenceXu, Yaming; Li, Zhitian; Gu, Yunlong. Synthesis of thioctamide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Arner ES, Nordberg J, Holmgren A: Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74. [PubMed:8769129 ]
  2. Nordman T, Xia L, Bjorkhem-Bergman L, Damdimopoulos A, Nalvarte I, Arner ES, Spyrou G, Eriksson LC, Bjornstedt M, Olsson JM: Regeneration of the antioxidant ubiquinol by lipoamide dehydrogenase, thioredoxin reductase and glutathione reductase. Biofactors. 2003;18(1-4):45-50. [PubMed:14695919 ]
  3. Oizumi J, Hayakawa K: Liberation of lipoate by human serum lipoamidase from bovine heart pyruvate dehydrogenase. Biochem Biophys Res Commun. 1989 Jul 31;162(2):658-63. [PubMed:2502979 ]
  4. Nakai T, Nakagawa N, Maoka N, Masui R, Kuramitsu S, Kamiya N: Ligand-induced conformational changes and a reaction intermediate in branched-chain 2-oxo acid dehydrogenase (E1) from Thermus thermophilus HB8, as revealed by X-ray crystallography. J Mol Biol. 2004 Apr 2;337(4):1011-33. [PubMed:15033367 ]
  5. Wynn RM, Machius M, Chuang JL, Li J, Tomchick DR, Chuang DT: Roles of His291-alpha and His146-beta' in the reductive acylation reaction catalyzed by human branched-chain alpha-ketoacid dehydrogenase: refined phosphorylation loop structure in the active site. J Biol Chem. 2003 Oct 31;278(44):43402-10. Epub 2003 Aug 5. [PubMed:12902323 ]
  6. Panak KC, Ruiz OA, Giorgieri SA, Diaz LE: Direct determination of glutathione in human blood by micellar electrokinetic chromatography: simultaneous determination of lipoamide and lipoic acid. Electrophoresis. 1996 Oct;17(10):1613-6. [PubMed:8957191 ]

Enzymes

General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
P08559
Molecular weight:
43295.255
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
Reactions
Dihydrolipoamide + NAD → Lipoamide + NADH + Hydrogen Iondetails
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
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular weight:
48179.59
General function:
Involved in lyase activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The P protein binds the alpha-amino group of glycine through its pyridoxal phosphate cofactor; CO(2) is released and the remaining methylamine moiety is then transferred to the lipoamide cofactor of the H protein.
Gene Name:
GLDC
Uniprot ID:
P23378
Molecular weight:
112728.805