(S)-lipoic acid (CHEM022061)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:18:50 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022061
Identification
Common Name(S)-lipoic acid
ClassSmall Molecule
DescriptionThe (S)-enantiomer of lipoic acid. Not found in nature, it may exert detrimental effects on biosystems.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-(-)-Lipoic acidChEBI
(S)-1,2-Dithiolane-3-pentanoic acidChEBI
(S)-alpha-Lipoic acidChEBI
L-1,2-Dithiolane 3-valeric acidChEBI
L-6,8-Thioctic acidChEBI
L-6-Thioctic acidChEBI
Lipoic acidChEBI
S-LAChEBI
SLAChEBI
Thioctic acid L-formChEBI
(S)-(-)-LipoateGenerator
(S)-1,2-Dithiolane-3-pentanoateGenerator
(S)-a-LipoateGenerator
(S)-a-Lipoic acidGenerator
(S)-alpha-LipoateGenerator
(S)-α-lipoateGenerator
(S)-α-lipoic acidGenerator
L-1,2-Dithiolane 3-valerateGenerator
L-6,8-ThioctateGenerator
L-6-ThioctateGenerator
LipoateGenerator
Thioctate L-formGenerator
Acid, alpha-lipoicMeSH, HMDB
Thioctic acidMeSH, HMDB
alpha Lipoic acidMeSH, HMDB
(S)-LipoateGenerator
(-)-Thioctic acidHMDB
(3S)-1,2-Dithiolane-3-pentanoic acidHMDB
(S)-Lipoic acidHMDB
(S)-Thioctic acidHMDB
S-(-)-alpha-Lipoic acidHMDB
S-(-)-α-Lipoic acidHMDB
1,2-Dithiolane-3-valeric acidHMDB
1,2-Dithiolane-3-pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)valeric acidHMDB
6,8-Thioctic acidHMDB
6-Thioctic acidHMDB
ALAHMDB
Chemical FormulaC8H14O2S2
Average Molecular Mass206.326 g/mol
Monoisotopic Mass206.044 g/mol
CAS Registry Number1077-27-6
IUPAC Name5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid
Traditional NameS-LA
SMILES[H][C@]1(CCCCC(O)=O)CCSS1
InChI IdentifierInChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1
InChI KeyAGBQKNBQESQNJD-ZETCQYMHSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability21.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920000000-cf913d1d1afc04e5450cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-5910000000-294c510229247ef63f20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9600000000-f8f54eb79c5d4d5bef48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0920000000-5a823a30dd1fb434e5b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmu-1910000000-6f491a68afd82922e71bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-330e4766f82ed571497bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0970000000-0ae5b11a032d11c1ba6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-decf255617c1bbd69bfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-eb58a3d8135ba85d4283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-014d2ea36cfae0726a9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9500000000-9bbbd7b252fb9a0b438dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0014312
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLipoic_acid
Chemspider ID392857
ChEBI ID43796
PubChem Compound ID445125
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB24069
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10218658
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14991456
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15157071
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9252495
5. Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004.
6. REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4.