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Record Information
Version1.0
Created at2022-05-30 16:54:12 UTC
Updated at2022-05-30 16:54:12 UTC
NP-MRD IDNP0137497
Secondary Accession NumbersNone
Natural Product Identification
Common NameLipoic acid
DescriptionLipoate, also known as lipoic acid or 6,8-thioctic acid, 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. Lipoate is a weakly acidic compound (based on its pKa). Lipoate may be a unique E. Coli metabolite. In humans, lipoate is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Outside of the human body, lipoate has been detected, but not quantified in, broccoli and spinachs. This could make lipoate a potential biomarker for the consumption of these foods. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. Lipoic acid is found in Hyacinthoides non-scripta. It was first documented in 1994 (PMID: 7519986). Lipoate is a potentially toxic compound (PMID: 7548757).
Structure
Thumb
Synonyms
ValueSource
1,2-Dithiolane-3-pentanoic acidChEBI
1,2-Dithiolane-3-valeric acidChEBI
5-(1,2-Dithiolan-3-yl)valeric acidChEBI
5-(Dithiolan-3-yl)valeric acidChEBI
5-[3-(1,2-Dithiolanyl)]pentanoic acidChEBI
6,8-Thioctic acidChEBI
6,8-Thiotic acidChEBI
6-Thioctic acidChEBI
6-Thiotic acidChEBI
Acetate-replacing factorChEBI
alpha-Lipoic acidChEBI
alpha-LiponsaeureChEBI
BiletanChEBI
Liponic acidChEBI
ThioctansaeureChEBI
Thioctic acidChEBI
ThioctsaeureChEBI
ThioktsaeureChEBI
Lipoic acidKegg
DL-alpha-Lipoic acidKegg
DL-Thioctic acidKegg
ThiotominKegg
1,2-Dithiolane-3-pentanoateGenerator
1,2-Dithiolane-3-valerateGenerator
5-(1,2-Dithiolan-3-yl)valerateGenerator
5-(Dithiolan-3-yl)valerateGenerator
5-[3-(1,2-Dithiolanyl)]pentanoateGenerator
6,8-ThioctateGenerator
6,8-ThiotateGenerator
6-ThioctateGenerator
6-ThiotateGenerator
Acetic acid-replacing factorGenerator
a-LipoateGenerator
a-Lipoic acidGenerator
alpha-LipoateGenerator
Α-lipoateGenerator
Α-lipoic acidGenerator
a-LiponsaeureGenerator
Α-liponsaeureGenerator
LiponateGenerator
ThioctateGenerator
DL-a-LipoateGenerator
DL-a-Lipoic acidGenerator
DL-alpha-LipoateGenerator
DL-Α-lipoateGenerator
DL-Α-lipoic acidGenerator
DL-ThioctateGenerator
(R)-LipoateGenerator
Alpha LipogammaMeSH
Alpha Liponsaure sofotecMeSH
Alpha-LipogammaMeSH
Alpha-Lippon alMeSH
AlphaLipogammaMeSH
AlphaflamMeSH
Generosan brand OF thioctic acidMeSH
JuthiacMeSH
Liponsaure-ratiopharmMeSH
LiponsaureratiopharmMeSH
Merck dura brand OF thioctic acidMeSH
Pleomix Alpha NMeSH
Pleomix-Alpha NMeSH
Rosen brand OF thioctic acidMeSH
Thiogamma oralMeSH
TromliponMeSH
Trommsdorgg brand OF thioctic acidMeSH
Viatris brand OF thioctic acid tromethamineMeSH
alpha Lipoic acidMeSH
alpha-Liponsaure von CTMeSH
AlphaLiponaure heumannMeSH
AlphaLiponsaure von CTMeSH
biomo LiponMeSH
Esparma brand OF thioctic acidMeSH
Acid, alpha-lipoicMeSH
Alpha Lipon stadaMeSH
Alpha Lippon alMeSH
AlphaLipon stadaMeSH
AlphaLiponsaure sofotecMeSH
AlphaLippon alMeSH
Hexal brand OF thioctic acidMeSH
Injekt, thiogammaMeSH
Liponsaure ratiopharmMeSH
Pleomix AlphaMeSH
Stadapharm brand OF thioctic acidMeSH
Thioctacide TMeSH
Viatris brand OF thioctic acidMeSH
alpha Liponsaure von CTMeSH
AlphaVibolexMeSH
BiomoliponMeSH
Ratiopharm brand OF thioctic acidMeSH
Aliud brand OF thioctic acidMeSH
Alpha-Liponsaure sofotecMeSH
AzulipontMeSH
Illa brand OF thioctic acidMeSH
Illa brand OF thioctic acid tromethamineMeSH
MTW AlphaliponsaureMeSH
MTW Brand OF thioctic acidMeSH
Pharmacia brand OF thioctic acidMeSH
Pleomix-AlphaMeSH
PleomixAlphaMeSH
PleomixAlpha NMeSH
Q Pharm brand OF thioctic acidMeSH
Q-Pharm brand OF thioctic acidMeSH
Verla liponMeSH
Verla-liponMeSH
alpha Liponaure heumannMeSH
alpha VibolexMeSH
biomo-LiponMeSH
DuraliponMeSH
Alpha-Lipon stadaMeSH
Azupharma brand OF thioctic acidMeSH
FenintMeSH
Heumann brand OF thioctic acidMeSH
Juta brand OF thioctic acidMeSH
Lichtenstein brand OF thioctic acidMeSH
MTW-AlphaliponsaureMeSH
MTWAlphaliponsaureMeSH
NeuriumMeSH
Sofotec brand OF thioctic acidMeSH
ThioctacidMeSH
Thiogamma injektMeSH
Verla brand OF thioctic acidMeSH
VerlaLiponMeSH
Worwag brand OF thioctic acidMeSH
Worwag brand OF thioctic acid meglumineMeSH
alpha-Liponaure heumannMeSH
alpha-VibolexMeSH
biomo Brand OF thioctic acidMeSH
CT Arzneimittel brand OF thioctic acidMeSH
CT-Arzneimittel brand OF thioctic acidMeSH
Espa liponMeSH
Espa-liponMeSH
EspaliponMeSH
Chemical FormulaC8H14O2S2
Average Mass206.3260 Da
Monoisotopic Mass206.04352 Da
IUPAC Name5-(1,2-dithiolan-3-yl)pentanoic acid
Traditional Name6,8-thioctic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCCCC1CCSS1
InChI Identifier
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChI KeyAGBQKNBQESQNJD-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hyacinthoides non-scriptaLOTUS Database
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
StateNot Available
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
Polarizability22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004339
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00725
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLipoic_acid
METLIN IDNot Available
PubChem Compound864
PDB IDNot Available
ChEBI ID16494
Good Scents IDNot Available
References
General References
  1. Christen U, Quinn J, Yeaman SJ, Kenna JG, Clarke JB, Gandolfi AJ, Gut J: Identification of the dihydrolipoamide acetyltransferase subunit of the human pyruvate dehydrogenase complex as an autoantigen in halothane hepatitis. Molecular mimicry of trifluoroacetyl-lysine by lipoic acid. Eur J Biochem. 1994 Aug 1;223(3):1035-47. doi: 10.1111/j.1432-1033.1994.tb19082.x. [PubMed:7519986 ]
  2. Frey N, Christen U, Jeno P, Yeaman SJ, Shimomura Y, Kenna JG, Gandolfi AJ, Ranek L, Gut J: The lipoic acid containing components of the 2-oxoacid dehydrogenase complexes mimic trifluoroacetylated proteins and are autoantigens associated with halothane hepatitis. Chem Res Toxicol. 1995 Jul-Aug;8(5):736-46. doi: 10.1021/tx00047a014. [PubMed:7548757 ]