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Record Information
Version1.0
Creation Date2016-09-30 22:46:09 UTC
Update Date2020-05-21 16:28:29 UTC
BMDB IDBMDB0001451
Secondary Accession Numbers
  • BMDB01451
Metabolite Identification
Common NameLipoic acid
DescriptionLipoic acid, also known as RLA or a-lipoate, 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. Lipoic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Lipoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoic acid exists in all living species, ranging from bacteria to humans. In cattle, lipoic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
(+)-alpha-Lipoic acidChEBI
(R)-(+)-LipoateChEBI
(R)-(+)-Lipoic acidChEBI
(R)-1,2-Dithiolane-3-pentanoic acidChEBI
(R)-1,2-Dithiolane-3-valeric acidChEBI
(R)-6,8-Thioctic acidChEBI
alpha-Lipoic acidChEBI
Lipoic acidChEBI
R-(+)-Lipoic acidChEBI
R-LAChEBI
RLAChEBI
Thioctic acidChEBI
Thioctic acid D-formChEBI
1,2-Dithiolane-3R-pentanoic acidKegg
(+)-a-LipoateGenerator
(+)-a-Lipoic acidGenerator
(+)-alpha-LipoateGenerator
(+)-Α-lipoateGenerator
(+)-Α-lipoic acidGenerator
(R)-1,2-Dithiolane-3-pentanoateGenerator
(R)-1,2-Dithiolane-3-valerateGenerator
(R)-6,8-ThioctateGenerator
a-LipoateGenerator
a-Lipoic acidGenerator
alpha-LipoateGenerator
Α-lipoateGenerator
Α-lipoic acidGenerator
LipoateGenerator
R-(+)-LipoateGenerator
ThioctateGenerator
Thioctate D-formGenerator
1,2-Dithiolane-3R-pentanoateGenerator
(R)-LipoateGenerator
Alpha Lippon alHMDB
Alpha-Lippon alHMDB
AlphaLippon alHMDB
AlphaflamHMDB
Hexal brand OF thioctic acidHMDB
Injekt, thiogammaHMDB
Liponsaure ratiopharmHMDB
Liponsaure-ratiopharmHMDB
Stadapharm brand OF thioctic acidHMDB
Thioctacide THMDB
Verla liponHMDB
Viatris brand OF thioctic acidHMDB
alpha Liponaure heumannHMDB
alpha Liponsaure von CTHMDB
AlphaLiponsaure von CTHMDB
DuraliponHMDB
Ratiopharm brand OF thioctic acidHMDB
Aliud brand OF thioctic acidHMDB
Alpha-Liponsaure sofotecHMDB
AlphaLipon stadaHMDB
AzulipontHMDB
Heumann brand OF thioctic acidHMDB
Illa brand OF thioctic acidHMDB
Illa brand OF thioctic acid tromethamineHMDB
Juta brand OF thioctic acidHMDB
MTW AlphaliponsaureHMDB
Pleomix AlphaHMDB
PleomixAlphaHMDB
PleomixAlpha NHMDB
Q Pharm brand OF thioctic acidHMDB
Q-Pharm brand OF thioctic acidHMDB
Thiogamma injektHMDB
alpha VibolexHMDB
AlphaVibolexHMDB
Biomo brand OF thioctic acidHMDB
Biomo-liponHMDB
BiomoliponHMDB
CT-Arzneimittel brand OF thioctic acidHMDB
Acid, alpha-lipoicHMDB
Alpha LipogammaHMDB
Alpha Lipon stadaHMDB
Alpha-LipogammaHMDB
Alpha-Lipon stadaHMDB
AlphaLipogammaHMDB
AlphaLiponsaure sofotecHMDB
FenintHMDB
JuthiacHMDB
Merck dura brand OF thioctic acidHMDB
Pleomix Alpha NHMDB
Rosen brand OF thioctic acidHMDB
Thiogamma oralHMDB
TromliponHMDB
Trommsdorgg brand OF thioctic acidHMDB
Viatris brand OF thioctic acid tromethamineHMDB
Worwag brand OF thioctic acidHMDB
Worwag brand OF thioctic acid meglumineHMDB
alpha Lipoic acidHMDB
alpha-Liponsaure von CTHMDB
alpha-VibolexHMDB
AlphaLiponaure heumannHMDB
Biomo liponHMDB
CT Arzneimittel brand OF thioctic acidHMDB
Esparma brand OF thioctic acidHMDB
Alpha Liponsaure sofotecHMDB
Azupharma brand OF thioctic acidHMDB
Generosan brand OF thioctic acidHMDB
Lichtenstein brand OF thioctic acidHMDB
LiponsaureratiopharmHMDB
MTW Brand OF thioctic acidHMDB
MTW-AlphaliponsaureHMDB
MTWAlphaliponsaureHMDB
NeuriumHMDB
Pharmacia brand OF thioctic acidHMDB
Pleomix-AlphaHMDB
Pleomix-Alpha NHMDB
Sofotec brand OF thioctic acidHMDB
ThioctacidHMDB
Verla brand OF thioctic acidHMDB
Verla-liponHMDB
VerlaLiponHMDB
alpha-Liponaure heumannHMDB
Espa liponHMDB
Espa-liponHMDB
EspaliponHMDB
(R)-Lipoic acidKEGG
Chemical FormulaC8H14O2S2
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
IUPAC Name5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
Traditional Namelipoic acid
CAS Registry Number1200-22-2
SMILES
OC(=O)CCCC[C@@H]1CCSS1
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-5900000000-716655e029db4b97efd9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0hbi-6920000000-011fb15a0f9ca4513029View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0940000000-dead1b29e79e0002da2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f8c-9200000000-b6035bdb4abd0d267297View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0059-9000000000-62e73cabbac1531f5145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1920000000-2b265e3ed116fbc0a2eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-2910000000-9142e84d978f4a481551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-8bdfe1c35977a8c80985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0940000000-6cecd351951f396a3035View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gr-6910000000-f169816d57d2290b0d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2c-9700000000-57ae386a681b98208a4bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Kidney
  • Liver
  • Milk
  • Neuron
  • Placenta
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001451
DrugBank IDDB00166
Phenol Explorer Compound IDNot Available
FooDB IDFDB022631
KNApSAcK IDC00000754
Chemspider ID5886
KEGG Compound IDC16241
BioCyc IDLIPOIC-ACID
BiGG ID35801
Wikipedia LinkLipoic_acid
METLIN ID126
PubChem Compound6112
PDB IDNot Available
ChEBI ID30314
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]

Enzymes

General function:
Involved in dihydrolipoyllysine-residue acetyltransfera
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
DLAT
Uniprot ID:
P11180
Molecular weight:
1066.0
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the activation of fatty acids by CoA to produce an acyl-CoA, the first step in fatty acid metabolism (PubMed:11382754, PubMed:10561077). Capable of activating medium-chain fatty acids (e.g. butyric (C4) to decanoic (C10) acids), and certain carboxylate-containing xenobiotics, e.g. benzoate (PubMed:10561077, PubMed:11382754). Also catalyzes the activation of lipoate to lipoyl-nucleoside monophosphate (PubMed:11382754). Activates lipoate with GTP at a 1000-fold higher rate than with ATP and activates both (R)- and (S)-lipoate to the respective lipoyl-GMP, with a preference for (R)-lipoate (PubMed:11382754).
Gene Name:
ACSM1
Uniprot ID:
Q9BEA2
Molecular weight:
64923.0
General function:
Energy production and conversion
Specific function:
Dihydrolipoamide succinyltransferase (E2) component of the 2-oxoglutarate dehydrogenase complex (By similarity). The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2) (By similarity). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A (By similarity).
Gene Name:
DLST
Uniprot ID:
P11179
Molecular weight:
48973.0
General function:
Energy production and conversion
Specific function:
Required for anchoring dihydrolipoamide dehydrogenase (E3) to the dihydrolipoamide transacetylase (E2) core of the pyruvate dehydrogenase complexes of eukaryotes. This specific binding is essential for a functional PDH complex.
Gene Name:
PDHX
Uniprot ID:
P22439
Molecular weight:
53886.0
General function:
Energy production and conversion
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). Within this complex, the catalytic function of this enzyme is to accept, and to transfer to coenzyme A, acyl groups that are generated by the branched-chain alpha-keto acid decarboxylase component.
Gene Name:
DBT
Uniprot ID:
P11181
Molecular weight:
53410.0
General function:
Amino acid transport and metabolism
Specific function:
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name:
AMT
Uniprot ID:
P25285
Molecular weight:
42869.0
General function:
Amino acid transport and metabolism
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The H protein (GCSH) shuttles the methylamine group of glycine from the P protein (GLDC) to the T protein (GCST).
Gene Name:
GCSH
Uniprot ID:
P20821
Molecular weight:
18791.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
Dihydrolipoate + NAD → Lipoic acid + NADHdetails