Details of the Drug

General Information of Drug (ID: DMNFCXW)

Drug Name
THIOCTIC ACID
Synonyms
dl-Thioctic acid; thioctic acid; 1077-28-7; 5-(1,2-Dithiolan-3-yl)pentanoic acid; DL-alpha-Lipoic acid; 1,2-dithiolane-3-pentanoic acid; Thioctacid; 6,8-Thioctic acid; 6-Thioctic acid; Lipothion; Biletan; dl-Lipoic acid; Tioctacid; Thioctsan; Liposan; Rac-lipoate; 1,2-Dithiolane-3-valeric acid; DL-6,8-Thioctic acid; alpha-Liponsaeure; DL-6-Thioctic acid; alpha-liponic acid; Thioktsaeure; Tioctidasi; (RS)-Lipoic acid; 6,8-Dithiooctanoic acid; espa-lipon; Thioctic acid dl-form; 62-46-4
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 206.3
Logarithm of the Partition Coefficient (xlogp) 1.7
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 11.5 mL/min/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.21 hours [2]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.1 L/kg [2]
Chemical Identifiers
Formula
C8H14O2S2
IUPAC Name
5-(dithiolan-3-yl)pentanoic acid
Canonical SMILES
C1CSSC1CCCCC(=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)
InChIKey
AGBQKNBQESQNJD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
864
ChEBI ID
CHEBI:16494
CAS Number
1077-28-7
TTD ID
D0P6PQ
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [3]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Drug Response [4]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [4]
Catalase (CAT) OTHEBX9R CATA_HUMAN Gene/Protein Processing [5]
Epididymal secretory glutathione peroxidase (GPX5) OTQMMNNT GPX5_HUMAN Gene/Protein Processing [5]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [6]
Glutamate--cysteine ligase regulatory subunit (GCLM) OT6CP234 GSH0_HUMAN Gene/Protein Processing [6]
Glutathione peroxidase 1 (GPX1) OTE2O72Q GPX1_HUMAN Gene/Protein Processing [5]
Glutathione peroxidase 3 (GPX3) OT6PK94R GPX3_HUMAN Gene/Protein Processing [5]
Glutathione reductase, mitochondrial (GSR) OTM2TUYM GSHR_HUMAN Gene/Protein Processing [5]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Investigations concerning the COX/5-LOX inhibiting and hydroxyl radical scavenging potencies of novel 4,5-diaryl isoselenazoles. Eur J Med Chem. 2008 Jun;43(6):1152-9.
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem. 2008 Feb 14;51(3):347-72.
4 Reactive oxygen species mediate caspase activation and apoptosis induced by lipoic acid in human lung epithelial cancer cells through Bcl-2 down-regulation. J Pharmacol Exp Ther. 2006 Dec;319(3):1062-9. doi: 10.1124/jpet.106.110965. Epub 2006 Sep 21.
5 Cytoprotective effect of alpha-lipoic acid on paraquat-exposed human bronchial epithelial cells via activation of nuclear factor erythroid related factor-2 pathway. Biol Pharm Bull. 2013;36(5):802-11.
6 (R)-alpha-lipoic acid protects retinal pigment epithelial cells from oxidative damage. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4302-10. doi: 10.1167/iovs.04-1098.
7 HMOX1 and NQO1 genes are upregulated in response to contact sensitizers in dendritic cells and THP-1 cell line: role of the Keap1/Nrf2 pathway. Toxicol Sci. 2009 Feb;107(2):451-60.