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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:04 UTC
Update Date2023-02-21 17:17:44 UTC
HMDB IDHMDB0012210
Secondary Accession Numbers
  • HMDB12210
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).
Structure
Data?1676999864
Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-Dimercapto-octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
Dihydro-alpha-lipoic acidChEBI
Dihydro-lipoic acidChEBI
Dihydrothioctic acidChEBI
Dihydrolipoic acidKegg
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-Dimercapto-octanoateGenerator
6,8-DimercaptooctanoateGenerator
Dihydro-a-lipoateGenerator
Dihydro-a-lipoic acidGenerator
Dihydro-alpha-lipoateGenerator
Dihydro-α-lipoateGenerator
Dihydro-α-lipoic acidGenerator
Dihydro-lipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Dihydrolipoic acid, (+-)-isomerMeSH, HMDB
Dihydrolipoic acid, sodium saltMeSH, HMDB
Chemical FormulaC8H16O2S2
Average Molecular Weight208.341
Monoisotopic Molecular Weight208.059171136
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
CAS Registry Number462-20-4
SMILES
OC(=O)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyIZFHEQBZOYJLPK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Thia fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.24ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity55.94 m³·mol⁻¹ChemAxon
Polarizability23.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.17531661259
DarkChem[M-H]-142.31631661259
DeepCCS[M+H]+147.24730932474
DeepCCS[M-H]-144.76530932474
DeepCCS[M-2H]-180.34930932474
DeepCCS[M+Na]+155.57930932474
AllCCS[M+H]+145.232859911
AllCCS[M+H-H2O]+141.832859911
AllCCS[M+NH4]+148.532859911
AllCCS[M+Na]+149.432859911
AllCCS[M-H]-150.632859911
AllCCS[M+Na-2H]-152.532859911
AllCCS[M+HCOO]-154.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrolipoateOC(=O)CCCCC(S)CCS3224.6Standard polar33892256
DihydrolipoateOC(=O)CCCCC(S)CCS1676.0Standard non polar33892256
DihydrolipoateOC(=O)CCCCC(S)CCS1814.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrolipoate,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(S)CCS1917.3Semi standard non polar33892256
Dihydrolipoate,1TMS,isomer #2C[Si](C)(C)SC(CCS)CCCCC(=O)O1978.8Semi standard non polar33892256
Dihydrolipoate,1TMS,isomer #3C[Si](C)(C)SCCC(S)CCCCC(=O)O2027.9Semi standard non polar33892256
Dihydrolipoate,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C1994.1Semi standard non polar33892256
Dihydrolipoate,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C2009.5Standard non polar33892256
Dihydrolipoate,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C2285.5Standard polar33892256
Dihydrolipoate,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C2052.5Semi standard non polar33892256
Dihydrolipoate,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C2010.4Standard non polar33892256
Dihydrolipoate,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C2389.1Standard polar33892256
Dihydrolipoate,2TMS,isomer #3C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C2127.0Semi standard non polar33892256
Dihydrolipoate,2TMS,isomer #3C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C2129.4Standard non polar33892256
Dihydrolipoate,2TMS,isomer #3C[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C2490.6Standard polar33892256
Dihydrolipoate,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C2171.9Semi standard non polar33892256
Dihydrolipoate,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C2206.3Standard non polar33892256
Dihydrolipoate,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C2193.5Standard polar33892256
Dihydrolipoate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS2139.8Semi standard non polar33892256
Dihydrolipoate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SC(CCS)CCCCC(=O)O2211.1Semi standard non polar33892256
Dihydrolipoate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCCC(S)CCCCC(=O)O2264.2Semi standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C2501.6Semi standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C2446.5Standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C2477.7Standard polar33892256
Dihydrolipoate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C2563.6Semi standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C2451.7Standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C2576.3Standard polar33892256
Dihydrolipoate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C2647.4Semi standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C2558.9Standard non polar33892256
Dihydrolipoate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCCC(CCCCC(=O)O)S[Si](C)(C)C(C)(C)C2588.8Standard polar33892256
Dihydrolipoate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2898.9Semi standard non polar33892256
Dihydrolipoate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2816.2Standard non polar33892256
Dihydrolipoate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2522.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dihydrolipoate GC-EI-TOF (Non-derivatized)splash10-0007-5920000000-99648df42c67f7327a1d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrolipoate GC-EI-TOF (Non-derivatized)splash10-0007-5920000000-99648df42c67f7327a1d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kij-5900000000-7564ff734a37b263a7ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9520000000-35f52ace937d40f6ba6e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrolipoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOFsplash10-00di-0900000000-832657635f2c81515eac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOFsplash10-00di-1900000000-832657635f2c81515eac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOFsplash10-0ab9-0690000000-bb3d2691ed5ceb749b8c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Positive-QTOFsplash10-0a4l-0920000000-203769a6e5514dfdacce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOFsplash10-0bvl-0900000000-e0d6ca4b105aaeae3f102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Positive-QTOFsplash10-06vi-9500000000-30fa7bade921a70952d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOFsplash10-0ab9-0960000000-352daa80c3d73329d4b82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOFsplash10-0a4i-1930000000-dee930722526f680e10d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Negative-QTOFsplash10-053r-9300000000-c53948709f447f46266c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Positive-QTOFsplash10-0a4i-0930000000-266230745999efddf6dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Positive-QTOFsplash10-0ufr-2900000000-24ea3b6c12cfdd8e2cac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Positive-QTOFsplash10-0006-9300000000-a87ea4acfc88c77960a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 10V, Negative-QTOFsplash10-0a4i-0190000000-212b987ce9dfd82aaeb62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 20V, Negative-QTOFsplash10-0a4r-3920000000-1948f3bf848db6d6ef452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrolipoate 40V, Negative-QTOFsplash10-001l-9400000000-39e9224d6c07b378fb5a2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB028855
KNApSAcK IDNot Available
Chemspider ID408
KEGG Compound IDC02147
BioCyc ID6-S-ACETYL-DIHYDROLIPOATE
BiGG IDNot Available
Wikipedia LinkDihydrolipoic_acid
METLIN IDNot Available
PubChem Compound421
PDB IDNot Available
ChEBI ID18047
Food Biomarker OntologyNot Available
VMH IDC02147
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prehn JH, Karkoutly C, Nuglisch J, Peruche B, Krieglstein J: Dihydrolipoate reduces neuronal injury after cerebral ischemia. J Cereb Blood Flow Metab. 1992 Jan;12(1):78-87. [PubMed:1345759 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.