Structure Database (LMSD)
Common Name
Lipoic acid
Systematic Name
1,2-dithiolane-3R-pentanoic acid
Synonyms
- R-Lipoic acid
3D model of Lipoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
(R)-α-Lipoic acid is the naturally occurring enantiomer of lipoic acid, a cyclic disulfide antioxidant.1 It acts as a cofactor in 2-oxo dehydrogenase complex reactions, where it is reduced to dihydrolipoic acid (DHLA). (R)-α-Lipoic acid (100 mg/kg per day) decreases serum levels of malondialdehyde (MDA) and increases the activity of superoxide dismutase (SOD) and total antioxidative capabilities (T-AOC) in a mouse model of accelerated senescence induced by D-galactose .2 It also reduces the escape latency in the Morris water maze compared to both D-galactose and vehicle control groups and rescues decreases in neural progenitor cell proliferation in the hippocampal dentate gyrus.
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
AGBQKNBQESQNJD-SSDOTTSWSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
OC(CCCC[C@@]1([H])SSCC1)=O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
12
Rings
1
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
186.56
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
3.36
Molar Refractivity
55.56
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Updated at
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