Human Metabolome Database Version 3.5

Showing metabocard for Lipoamide (HMDB00962)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:53 -0600
HMDB ID HMDB00962
Secondary Accession Numbers
  • HMDB06877
  • HMDB06950
Metabolite Identification
Common Name Lipoamide
Description Lipoamide is the oxidized form of glutathione. (PMID:8957191 Link_out). 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. (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,2-Dithiolane-3-pentanamide
  2. 5-(1,2-Dithiolan-3-yl)-pentanamide
  3. 5-(1,2-Dithiolan-3-yl)pentanamide
  4. 5-(1,2-Dithiolan-3-yl)valeramide
  5. 5-(Dithiolan-3-yl)valeramide
  6. alpha-Lipoate
  7. alpha-Lipoic acid
  8. alpha-Lipoic acid amide
  9. Dl-6-Thioctic amide
  10. DL-lipoamide
  11. Lipamide
  12. Lipoacin
  13. Lipoamid
  14. Lipoicin
  15. Lipozyme
  16. Lypoaran
  17. Pathoclon
  18. Thioami
  19. Thioctamid
  20. Thioctamide
  21. Thioctic acid amide
  22. Thioctic acid amide (jan)
  23. Thiotomin
  24. Ticolin
  25. Vitamin N
Chemical Formula C8H15NOS2
Average Molecular Weight 205.341
Monoisotopic Molecular Weight 205.059505487
IUPAC Name 5-(1,2-dithiolan-3-yl)pentanamide
Traditional IUPAC Name lipoamide
CAS Registry Number 940-69-2
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 Key FCCDDURTIIUXBY-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Dithiolanes
Sub Class Lipoamides
Other Descriptors
  • Dithiolanes
  • N-acyl Amines
  • Primary amides(Lipidmaps)
  • a small molecule(Cyc)
  • dithiolanes(ChEBI)
  • monocarboxylic acid amide(ChEBI)
Substituents
  • Carboxamide Group
  • Organic Disulfide
  • Primary Carboxylic Acid Amide
Direct Parent Lipoamides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 126.0 - 129.0 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.1 g/L ALOGPS
LogP 2.30 ALOGPS
LogP 1.31 ChemAxon
LogS -3.31 ALOGPS
pKa (strongest acidic) 16.45 ChemAxon
pKa (strongest basic) -0.58 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 43.09 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 56.19 ChemAxon
Polarizability 22.38 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations Not Available
Tissue Location
  • Placenta
Pathways
Name SMPDB Link KEGG Link
Valine, Leucine and Isoleucine Degradation SMP00032 map00280 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022340
KNApSAcK ID Not Available
Chemspider ID 840 Link_out
KEGG Compound ID C00248 Link_out
BioCyc ID LIPOAMIDE Link_out
BiGG ID 34384 Link_out
Wikipedia Link Lipoamide Link_out
NuGOwiki Link HMDB00962 Link_out
Metagene Link HMDB00962 Link_out
METLIN ID 3372 Link_out
PubChem Compound 863 Link_out
PDB ID Not Available
ChEBI ID 17460 Link_out
References
Synthesis Reference Xu, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
Reactions: Not Available
Gene Name: PDHA1
Uniprot ID: P08559 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dihydrolipoyl dehydrogenase, mitochondrial
Reactions:
Dihydrolipoamide + NAD unknown Lipoamide + NADH + Hydrogen Ion details
Gene Name: DLD
Uniprot ID: P09622 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
Reactions: Not Available
Gene Name: BCKDHA
Uniprot ID: P12694 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoglutarate dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: OGDH
Uniprot ID: Q02218 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycine dehydrogenase [decarboxylating], mitochondrial
Reactions: Not Available
Gene Name: GLDC
Uniprot ID: P23378 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA