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:CID_864; ChEMBL:CHEMBL33864; ChEBI:CHEBI:16494; FDASRS:73Y7P0K73Y; SureChEMBL:SCHEMBL51065; MolPort-002-461-878
Chemical structure download


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
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 0.554182


Thioctic acid
ADME 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
Number of Brenk structural alerts SwissADME 1
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001485ENSG00000197299BLM641ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL
TAR_EXP_000011ENSG00000126261UBA210054ChEMBL
TAR_EXP_000012ENSG00000142230SAE110055BindingDB, ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL
TAR_EXP_001343ENSG00000114200BCHE590BindingDB
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000356ENSG00000114867EIF4G11981BindingDB
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000559ENSG00000185513L3MBTL126013ChEMBL
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL