Record Information
Version1.0
Creation date2011-09-21 00:17:08 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022631
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLipoic acid
DescriptionA vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia [HMDB]
CAS Number1200-22-2
Structure
Thumb
Synonyms
SynonymSource
(+)-alpha-Lipoic acidChEBI, HMDB
(R)-(+)-LipoateChEBI, KEGG
(R)-(+)-Lipoic acidChEBI, Generator
(R)-1,2-Dithiolane-3-pentanoic acidChEBI, HMDB
(R)-1,2-Dithiolane-3-valeric acidChEBI, HMDB
(R)-6,8-Thioctic acidChEBI, HMDB
alpha-Lipoic acidChEBI, HMDB
Lipoic acidChEBI, HMDB
R-(+)-Lipoic acidChEBI, KEGG
R-LAChEBI, HMDB
RLAChEBI, HMDB
Thioctic acidChEBI, HMDB
Thioctic acid D-formChEBI, HMDB
(+)-a-LipoateGenerator, HMDB
(+)-a-Lipoic acidGenerator, HMDB
(+)-alpha-LipoateGenerator, HMDB
(+)-α-lipoateGenerator, HMDB
(+)-α-lipoic acidGenerator, HMDB
(R)-LipoateGenerator
(R)-1,2-Dithiolane-3-pentanoateGenerator, HMDB
(R)-1,2-Dithiolane-3-valerateGenerator, HMDB
(R)-6,8-ThioctateGenerator, HMDB
a-LipoateGenerator, HMDB
a-Lipoic acidGenerator, HMDB
alpha-LipoateGenerator, HMDB
α-lipoateGenerator, HMDB
α-Lipoic acidGenerator, HMDB
LipoateGenerator, HMDB
R-(+)-LipoateGenerator
ThioctateGenerator, HMDB
Thioctate D-formGenerator, HMDB
Acid, alpha-lipoicMeSH, HMDB
alpha Lipoic acidMeSH, HMDB
1,2-Dithiolane-3R-pentanoic acidKEGG
1,2-Dithiolane-3R-pentanoateGenerator
(R)-Lipoic acidKEGG
(3R)-1,2-Dithiolane-3-pentanoic acidHMDB
(R)-(+)-1,2-Dithiolane-3-pentanoic acidHMDB
(R)-(+)-alpha-Lipoic acidHMDB
(R)-(+)-α-Lipoic acidHMDB
(R)-5-(1,2-Dithiolan-3-yl)pentanoicacidHMDB
(R)-alpha-Lipoic acidHMDB
(R)-α-Lipoic acidHMDB
ALAHMDB
alpha-(+)-Lipoic acidHMDB
α-(+)-Lipoic acidHMDB
1,2-Dithiolane-3-valeric acidHMDB
5-(1,2-Dithiolan-3-yl)pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)valeric acidHMDB
6,8-Thioctic acidHMDB
6-Thioctic acidHMDB
(+-)-1,2-Dithiolane-3-pentanoatehmdb
(+-)-1,2-Dithiolane-3-pentanoic acidhmdb
(+-)-1,2-Dithiolane-3-valeratehmdb
(+-)-1,2-Dithiolane-3-valeric acidhmdb
(RS)-alpha-Lipoatehmdb
(RS)-alpha-Lipoic acidhmdb
(RS)-Lipoatehmdb
(RS)-Lipoic acidhmdb
(S)-(−)-lipoic acidHMDB
(S)-1,2-Dithiolane-3-pentanoic acidHMDB
(S)-alpha-Lipoic acidHMDB
1,2-Dithiolane-3-pentanoatehmdb
1,2-Dithiolane-3-pentanoic acidhmdb
1,2-Dithiolane-3-valeratehmdb
5-(1,2-Dithiolan-3-yl)pentanoatehmdb
5-(1,2-Dithiolan-3-yl)valeratehmdb
5-(Dithiolan-3-yl)valeratehmdb
5-(Dithiolan-3-yl)valeric acidhmdb
5-[3-(1,2-dithiolanyl)]pentanoatehmdb
5-[3-(1,2-dithiolanyl)]pentanoic acidhmdb
6-Thioctatehmdb
6-Thiotatehmdb
6-Thiotic acidhmdb
6,8-Dithiooctanoatehmdb
6,8-Dithiooctanoic acidhmdb
6,8-Thioctatehmdb
6,8-Thiotatehmdb
6,8-Thiotic acidhmdb
acetate replacing factorhmdb
Acetate-replacing factorhmdb
alpha Lipoatehmdb
alpha-Liponatehmdb
alpha-Liponic acidhmdb
alpha-Liponsaeurehmdb
Biletanhmdb
delta-[3-(1,2-dithiacyclopentyl)]pentanoatehmdb
delta-[3-(1,2-dithiacyclopentyl)]pentanoic acidhmdb
DL-1,2-Dithiolane 3-valeratehmdb
DL-1,2-Dithiolane 3-valeric acidhmdb
DL-6-Thioctatehmdb
DL-6-Thioctic acidhmdb
DL-6,8-Dithiooctanoatehmdb
DL-6,8-Dithiooctanoic acidhmdb
DL-6,8-Thioctatehmdb
DL-6,8-Thioctic acidhmdb
DL-alpha-Lipoatehmdb
DL-alpha-Lipoic acidhmdb
dl-Lipoatehmdb
dl-Lipoic acidhmdb
dl-Thioctatehmdb
dl-Thioctic acidhmdb
DL-Thioctic acid > 98%hmdb
Heparliponhmdb
L-1,2-Dithiolane 3-valeric acidHMDB
L-6-Thioctic acidHMDB
L-6,8-Thioctic acidHMDB
Liphmdb
liponatehmdb
liponic acidhmdb
Liposanhmdb
Lipothionhmdb
Protogen Ahmdb
Pyruvate oxidation factorhmdb
R-Lipoatehmdb
R-Lipoic acidhmdb
Rac-lipoatehmdb
Rac-lipoic acidhmdb
S-LAHMDB
SLAHMDB
Thioctacidhmdb
Thioctanhmdb
Thioctic acid d-formhmdb
Thioctic acid dl-formhmdb
Thioctic acid L-formHMDB
Thioctidasehmdb
Thioctsanhmdb
Thioktsaeurehmdb
Thiooctanoatehmdb
Thiooctanoic acidhmdb
Tioctacidhmdb
Tioctanhmdb
Tioctidasihmdb
Tioctidasi acetate replacing factorhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.75ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability21.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H14O2S2
IUPAC name5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
InChI IdentifierInChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
InChI KeyAGBQKNBQESQNJD-SSDOTTSWSA-N
Isomeric SMILESOC(=O)CCCC[C@@H]1CCSS1
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
Classification
Description Belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoic acids and derivatives
Direct ParentLipoic acids and derivatives
Alternative Parents
Substituents
  • Lipoic_acid_derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • 1,2-dithiolane
  • Organic disulfide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
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
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-4900000000-59fc063b5aa5a8b5db19Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MSLipoic acid, non-derivatized, GC-MS Spectrumsplash10-0aba-3900000000-46fc1d57abcc26f6720eSpectrum
GC-MSLipoic acid, non-derivatized, GC-MS Spectrumsplash10-0aba-3900000000-46fc1d57abcc26f6720eSpectrum
GC-MSLipoic acid, non-derivatized, GC-MS Spectrumsplash10-0aba-3900000000-46fc1d57abcc26f6720eSpectrum
GC-MSLipoic acid, non-derivatized, GC-MS Spectrumsplash10-0aba-3900000000-46fc1d57abcc26f6720eSpectrum
Predicted GC-MSLipoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ufu-5900000000-716655e029db4b97efd9Spectrum
Predicted GC-MSLipoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0hbi-6920000000-011fb15a0f9ca4513029Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0940000000-dead1b29e79e0002da2aSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f8c-9200000000-b6035bdb4abd0d267297Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0059-9000000000-62e73cabbac1531f5145Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0940000000-6cecd351951f396a3035Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gr-6910000000-f169816d57d2290b0d9eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2c-9700000000-57ae386a681b98208a4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1920000000-2b265e3ed116fbc0a2eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-2910000000-9142e84d978f4a481551Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-8bdfe1c35977a8c80985Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0970000000-0ae5b11a032d11c1ba6dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-decf255617c1bbd69bfbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-eb58a3d8135ba85d4283Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-014d2ea36cfae0726a9eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9500000000-9bbbd7b252fb9a0b438dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID392857
ChEMBL IDNot Available
KEGG Compound IDC00725
Pubchem Compound ID445125
Pubchem Substance IDNot Available
ChEBI ID16494
Phenol-Explorer IDNot Available
DrugBank IDDB00166
HMDB IDHMDB14312
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 IDLipoic acid
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
Enzymes
NameGene NameUniProt ID
Lipoyltransferase 1, mitochondrialLIPT1Q9Y234
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference