Showing metabocard for Lipoic acid (BMDB0001451)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:09 UTC
Update Date2020-05-21 16:28:29 UTC
MCDB ID BMDB0001451
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-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
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-5900000000-716655e029db4b97efd92016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0hbi-6920000000-011fb15a0f9ca45130292017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0940000000-dead1b29e79e0002da2a2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f8c-9200000000-b6035bdb4abd0d2672972012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0059-9000000000-62e73cabbac1531f51452012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-9100000000-e420d2c931e889befcfa2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0229-6900000000-90386d8704ab5bfe8e702021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-042d27906c9bde31821f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-9000000000-6572cec5a1c9f68d96792021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0940000000-6cecd351951f396a30352016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gr-6910000000-f169816d57d2290b0d9e2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0m2c-9700000000-57ae386a681b98208a4b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1920000000-2b265e3ed116fbc0a2ea2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-2910000000-9142e84d978f4a4815512016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-8bdfe1c35977a8c809852016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0970000000-0ae5b11a032d11c1ba6d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-decf255617c1bbd69bfb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6900000000-eb58a3d8135ba85d42832021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-014d2ea36cfae0726a9e2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a02021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9500000000-9bbbd7b252fb9a0b438d2021-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0001451
DrugBank IDDB00166
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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 ]