Structure Database (LMSD)

Common Name
Lipoic acid
Systematic Name
1,2-dithiolane-3R-pentanoic acid
Synonyms
  • R-Lipoic acid
LM ID
LMFA01130001
Formula
Exact Mass
Calculate m/z
206.043524
Status
Curated



Classification

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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