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alpha-Lipoic acid

Athanor · official

C8H14O2S2 · 206.3 g/mol

IUPAC name: 5-[(3R)-dithiolan-3-yl]pentanoic acid

Also called thioctic acid, lipoate, ALA, lipoamide precursor

Vitamins
Open in Athanor
The structure of alpha-Lipoic acid
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
5-[(3R)-dithiolan-3-yl]pentanoic acid
Synonyms
thioctic acid, lipoate, ALA
+ 41 more

lipoamide precursor, lipoic acid, (R)-lipoic acid, (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid, (R)-alpha-Lipoic acid, D-Thioctic acid, (R)-(+)-1,2-Dithiolane-3-pentanoic acid, R-(+)-Thioctic acid, (+)-alpha-Lipoic acid, 1,2-Dithiolane-3-pentanoic acid, (3R)-, R-alpha-Lipoic acid, Thioctic acid d-form, 5-[(3R)-dithiolan-3-yl]pentanoic acid, Berlition, Thiogamma, Lipoec, Tiobec, 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid, R-Lipoic acid, (R)-(+)-lipoic acid, (R)-1,2-Dithiolane-3-pentanoic acid, (R)-6,8-thioctic acid, 1,2-Dithiolane-3R-pentanoic acid, (R)-(+)-a-Lipoic acid, (R)-1,2-Dithiolane-3-valeric Acid, alpha-(+)-Lipoic acid, MFCD01631142, (r)-(+)-alpha-lipoic acid, R-(+)-Lipoic acid, Lipoic acid (Standard), R-LA, VLL71EBS9Z, (3R)-1,2-Dithiolane-3-pentanoic Acid, C8H14O2S2, CHEMBL134342, Heparlipon, R-(+)-alpha-Lipoic acid, (R)-(+)-|A-Lipoic Acid, (R)-alpha-Thioctic Acid, Thioderm, Tiobec Retard

Molecular formula
C8H14O2S2
Empirical formula
C4H7OS
Molecular weight
206.3 g/mol
Exact mass
206.04352
CAS number
1200-22-2
PubChem CID
6112
Canonical SMILES
C1CSSC1CCCCC(=O)O
Isomeric SMILES
C1CSS[C@@H]1CCCCC(=O)O
InChI
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
InChIKey
AGBQKNBQESQNJD-SSDOTTSWSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
12
Rings
1
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.88
H-bond donors
1
H-bond acceptors
3 computed here · PubChem 4
Rotatable bonds
5
TPSA (Ų)
37.3 computed here · PubChem 87.9
Formal charge
0
XLogP3
1.7 PubChem
Complexity
150 PubChem
Stereocenters
1 definedCIP: C8: R
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C46.57%
  • H6.84%
  • O15.51%
  • S31.08%

Isotope pattern

100%206.04310%207.0469.9%208.040209.043210.038

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
2.79 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-2.54 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.17 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 206.33
  • log P ≤ 5 (Crippen): 2.79
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 3

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Ambeed, ChemoSapiens, AKos Consulting & Solutions.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  6. ·Literature on PubChem

Data last updated 2026-10-14.