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Showing Compound Dihydrolipoate (FDB028855)

Record Information
Version1.0
Creation date2011-09-21 01:46:12 UTC
Update date2019-11-26 03:21:29 UTC
Primary IDFDB028855
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]. Dihydrolipoate is found in many foods, some of which are radish (variety), rapini, mamey sapote, and brassicas.
CAS Number462-20-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
6,8-bis-sulfanyloctanoatehmdb
6,8-bis-sulfanyloctanoic acidhmdb
6,8-dimercapto-Octanoatehmdb
6,8-dimercapto-Octanoic acidhmdb
6,8-disulfanyloctanoatehmdb
6,8-disulfanyloctanoic acidhmdb
D,l-dihydrolipoatehmdb
D,l-dihydrolipoic acidhmdb
dihydro-a-lipoatehmdb
dihydro-a-lipoic acidhmdb
dihydro-DL-alpha-lipoatehmdb
dihydro-DL-alpha-lipoic acidhmdb
dihydro-Lipoatehmdb
dihydro-Lipoic acidhmdb
dihydro-α-lipoateGenerator
dihydro-α-lipoic acidGenerator
dihydrolipoatehmdb
dihydrolipoic acidhmdb
dl-Dihydro-a-6-thioctic acidhmdb
dl-Dihydro-alpha-6-thioctic acidhmdb
reduced DL-6,8-Thioctic acidhmdb
reduced Lipoatehmdb
reduced Lipoic acidhmdb
Predicted 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
Chemical FormulaC8H16O2S2
IUPAC name6,8-disulfanyloctanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CCCCC(S)CCS
Average Molecular Weight208.341
Monoisotopic Molecular Weight208.059171136
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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-MSDihydrolipoate, non-derivatized, GC-MS Spectrumsplash10-0007-5920000000-99648df42c67f7327a1dSpectrum
GC-MSDihydrolipoate, non-derivatized, GC-MS Spectrumsplash10-0007-5920000000-99648df42c67f7327a1dSpectrum
Predicted GC-MSDihydrolipoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kij-5900000000-7564ff734a37b263a7acSpectrum
Predicted GC-MSDihydrolipoate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9520000000-35f52ace937d40f6ba6eSpectrum
Predicted GC-MSDihydrolipoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDihydrolipoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-832657635f2c81515eac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-832657635f2c81515eac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0690000000-bb3d2691ed5ceb749b8c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0920000000-203769a6e5514dfdacce2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvl-0900000000-e0d6ca4b105aaeae3f102017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vi-9500000000-30fa7bade921a70952d52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0960000000-352daa80c3d73329d4b82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1930000000-dee930722526f680e10d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9300000000-c53948709f447f46266c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0930000000-266230745999efddf6dd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-2900000000-24ea3b6c12cfdd8e2cac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-a87ea4acfc88c77960a62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-212b987ce9dfd82aaeb62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-3920000000-1948f3bf848db6d6ef452021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9400000000-39e9224d6c07b378fb5a2021-09-25View Spectrum
NMRNot Available
ChemSpider ID408
ChEMBL IDNot Available
KEGG Compound IDC02147
Pubchem Compound ID421
Pubchem Substance IDNot Available
ChEBI ID18047
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12210
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Glycine and Serine MetabolismSMP00004 map00260
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference