IMPPAT Phytochemical information: 
Thioctic acid
Thioctic acid
Summary

SMILES: OC(=O)CCCCC1SSCC1
InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChIKey: AGBQKNBQESQNJD-UHFFFAOYSA-N
DeepSMILES: OC=O)CCCCCSSCC5
Scaffold Graph/Node/Bond level: C1CSSC1
Scaffold Graph/Node level: C1CSSC1
Scaffold Graph level: C1CCCC1
Functional groups: CC(=O)O; CSSC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Dithiolanes
ClassyFire Subclass: Lipoic acids and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates
NP Classifier Class: Thia fatty acids
Synonymous chemical names:
alpha-lipoic-acid
External chemical identifiers:
CID:864; ChEMBL:CHEMBL33864; ChEBI:16494; FDASRS:73Y7P0K73Y; SureChEMBL:SCHEMBL51065; MolPort-002-461-878
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Thioctic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 206.33
Log P RDKit 2.79
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.88
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
Thioctic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5542
Thioctic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Thioctic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000006053CX3CL1786
ENSP00000212015SIRT1825
ENSP00000249042TST816
ENSP00000258743IL6851
ENSP00000261434LIAS954
ENSP00000264832ICAM1819
ENSP00000270202AKT1828
ENSP00000280346DLAT832
ENSP00000285930AKR1B1830
ENSP00000297494NOS3930
ENSP00000303211ACHE776
ENSP00000308699REC8786
ENSP00000310208SLC5A6976
ENSP00000319788NQO1722
ENSP00000329623BCL2700
ENSP00000330237CASP9700
ENSP00000337459NOS1786
ENSP00000342071LIPT1994
ENSP00000346103GPX4848
ENSP00000354532PNP900
ENSP00000354581GPX6889
ENSP00000354677GPX7786
ENSP00000368438PCNA800
ENSP00000373477GPX3889
ENSP00000374265GPX2880
ENSP00000380318MPST763
ENSP00000407375GPX1880
ENSP00000412237IL10800
ENSP00000419970POR837
ENSP00000423822GPX8786
ENSP00000434516TXNRD1733
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.