Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:38 UTC
HMDB IDHMDB0000985
Secondary Accession Numbers
  • HMDB0006948
  • HMDB00985
  • HMDB06948
Metabolite Identification
Common NameDihydrolipoamide
DescriptionDihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG).
Structure
Data?1582752169
Synonyms
ValueSource
6,8-DimercaptooctanamideChEBI
DihydrothioctamideChEBI
6,8-Bis-sulfanyloctanamideHMDB
6,8-Dimercapto-octanamideHMDB
6,8-DisulfanyloctanamideHMDB
Dihydrolipoamide, (+-)-isomerHMDB
Chemical FormulaC8H17NOS2
Average Molecular Weight207.357
Monoisotopic Molecular Weight207.075155551
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number3884-47-7
SMILESNot Available
InChI Identifier
InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)
InChI KeyVLYUGYAKYZETRF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentFatty amides
Alternative Parents
Substituents
  • Fatty amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular PropertiesNot Available
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.92831661259
DarkChem[M-H]-142.64131661259
AllCCS[M+H]+145.29732859911
AllCCS[M-H]-150.97632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrolipoamide,1TMS,#1C[Si](C)(C)OC(=N)CCCCC(S)CCS2065.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TMS,#2C[Si](C)(C)SC(CCS)CCCCC(=N)O2131.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TMS,#3C[Si](C)(C)SCCC(S)CCCCC(=N)O2174.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TMS,#4C[Si](C)(C)N=C(O)CCCCC(S)CCS2047.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=N)CCCCC(S)CCS2309.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TBDMS,#2CC(C)(C)[Si](C)(C)SC(CCS)CCCCC(=N)O2343.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TBDMS,#3CC(C)(C)[Si](C)(C)SCCC(S)CCCCC(=N)O2396.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dihydrolipoamide,1TBDMS,#4CC(C)(C)[Si](C)(C)N=C(O)CCCCC(S)CCS2264.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-936a7170a2da09aecf112016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoamide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9410000000-9f1410bc40e59db39d212017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 10V, Positive-QTOFsplash10-0a4l-0940000000-f34746a5ea022152ba752015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 20V, Positive-QTOFsplash10-052f-1900000000-99beaa28d558377887432015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 40V, Positive-QTOFsplash10-0m2i-9400000000-53152f2f29c03cd0cbcd2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 10V, Negative-QTOFsplash10-0ab9-1960000000-1e45a79f64407fb4dea82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 20V, Negative-QTOFsplash10-0ab9-5930000000-297b157da8ed63567faa2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 40V, Negative-QTOFsplash10-0006-9000000000-82e7dacb48c8cab103d42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 10V, Positive-QTOFsplash10-0ab9-0950000000-6272c55454b18f718c5d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 20V, Positive-QTOFsplash10-0w29-2900000000-a19052123ea01afd86132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 40V, Positive-QTOFsplash10-002v-9300000000-c0ae302dda03ee321d602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 10V, Negative-QTOFsplash10-0a4i-0090000000-1361b5d8ba6f1d1a13ef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 20V, Negative-QTOFsplash10-0pb9-5940000000-00e811c07c89a8896c7d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022352
KNApSAcK IDNot Available
Chemspider ID643
KEGG Compound IDC00579
BioCyc IDNot Available
BiGG ID35406
Wikipedia LinkDihydrolipoamide
METLIN ID5920
PubChem Compound663
PDB IDNot Available
ChEBI ID17694
Food Biomarker OntologyNot Available
VMH IDDHLAM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWeitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. [PubMed:15946682 ]
  2. Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. [PubMed:15826505 ]
  3. McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. [PubMed:15612914 ]
  4. Li XJ, Grunwald D, Mathieu J, Morel F, Stasia MJ: Crucial role of two potential cytosolic regions of Nox2, 191TSSTKTIRRS200 and 484DESQANHFAVHHDEEKD500, on NADPH oxidase activation. J Biol Chem. 2005 Apr 15;280(15):14962-73. Epub 2005 Jan 31. [PubMed:15684431 ]
  5. Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. [PubMed:15613977 ]

Enzymes

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 acyltransferase 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 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
DLST
Uniprot ID:
P36957
Molecular weight:
48754.87
General function:
Involved in acyltransferase activity
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:
DBT
Uniprot ID:
P11182
Molecular weight:
53486.635
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
DLAT
Uniprot ID:
Q86YI5
Molecular weight:
68996.0