Details of the Drug

General Information of Drug (ID: DMVDTR2)

Drug Name
Thymoquinone
Synonyms
490-91-5; Thymoquinon; p-Cymene-2,5-dione; 2-Isopropyl-5-methyl-1,4-benzoquinone; 2,5-CYCLOHEXADIENE-1,4-DIONE, 2-METHYL-5-(1-METHYLETHYL)-; 2-Isopropyl-5-methyl-p-benzoquinone; 2-Isopropyl-5-methylbenzoquinone; Polythymoquinone; 5-Isopropyl-2-methyl-1,4-benzoquinone; 2-Isopropyl-5-methylbenzo-1,4-quinone; p-Mentha-3,6-diene-2,5-dione; NSC 2228; 2-Isopropyl-5-methylcyclohexa-2,5-diene-1,4-dione; 2-Methyl-5-isopropyl-p-benzoquinone; 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione; NSC2228; 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione; UNII-O60IE26NUF; 2-Methyl-5-isopropyl-1,4-benzoquinone; O60IE26NUF; 2,5-Cyclohexadiene-1,4-dione, 5-isopropyl-2-methyl-; NSC-2228; 5-Isopropyl-2-methyl-p-benzoquinone; MFCD00001602; 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione; p-Mentha-3,6-diene-2,5-dione (8CI); 5-Isopropyl-2-methyl-2,5-Cyclohexadiene-1,4-dione; CCRIS 7152; EINECS 207-721-1; 2-methyl-5-(methylethyl)cyclohexa-2,5-diene-1,4-dione; BRN 1939047; thymolquinone; Thymoil; AI3-17758; 4hco; p-Mentha-3,5-dione; Spectrum_001237; SpecPlus_000457; Thymoquinone, >=98%; Spectrum2_000700; Spectrum3_001345; Spectrum4_001895; Spectrum5_000550; BSPBio_003129; KBioGR_002455; KBioSS_001717; DivK1c_006553; SCHEMBL542535; SPBio_000859; CHEMBL1672002; DTXSID9060079; KBio1_001497; KBio2_001717; KBio2_004285; KBio2_006853; KBio3_002349; Thymoquinone, analytical standard; CHEBI:113532; 2-Methyl-5-iso-propylbenzoquinone; BDBM166686; ZINC164367; BCP16946; HY-D0803; WLN: L6V DVJ B1 EY1&1; 2,4-dione, 5-isopropyl-2-methyl-; ANW-41600; CCG-40027; s4761; SBB008296; AKOS003368628; MCULE-9899033250; NCGC00178250-01; NCGC00178250-05; 73940-92-8; AK101679; AS-11327; 2-Isopropyl-5-methylbenzo-1,4-quinone #; 2,4-dione, 2-methyl-5-(1-methylethyl)-; CS-0012226; FT-0612708; ST45023960; K-9199; SR-05000002192; Q7799650; SR-05000002192-2; W-202869; BRD-K97566842-001-03-5; Thymoquinone; 2-isopropyl-5-methylbenzo-1,4-quinone; 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione (F8); 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9CI
Indication
Disease Entry ICD 11 Status REF
Polycystic ovarian syndrome 5A80.1 Phase 2/3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 164.2
Logarithm of the Partition Coefficient (xlogp) 2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C10H12O2
IUPAC Name
2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
Canonical SMILES
CC1=CC(=O)C(=CC1=O)C(C)C
InChI
InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
InChIKey
KEQHJBNSCLWCAE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10281
ChEBI ID
CHEBI:113532
CAS Number
490-91-5
DrugBank ID
DB16447
TTD ID
DY4OZ6

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Apoptosis regulator BAX (BAX) TTQ57WJ BAX_HUMAN Inhibitor [2]
Apoptosis regulator Bcl-2 (BCL-2) TTJGNVC BCL2_HUMAN Inhibitor [2]
Cellular tumor antigen p53 (TP53) TT7SBF5 P53_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [3]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [4]
Autophagy protein 5 (ATG5) OT4T5SMS ATG5_HUMAN Gene/Protein Processing [5]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [6]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [4]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [7]
BH3-interacting domain death agonist (BID) OTOSHSHU BID_HUMAN Gene/Protein Processing [5]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [3]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Gene/Protein Processing [3]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Polycystic ovarian syndrome
ICD Disease Classification 5A80.1
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Apoptosis regulator Bcl-2 (BCL-2) DTT BCL2 2.52E-02 0.17 0.72
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT04852510) Amelioration of Polycystic Ovary Syndrome Related Disorders by Supplementation of Thymoquinone and Metformin. U.S. National Institutes of Health.
2 Apoptosis as a mechanism for the treatment of adult T cell leukemia: promising drugs from benchside to bedside. Drug Discov Today. 2020 Jul;25(7):1189-1197.
3 Thymoquinone suppresses invasion and metastasis in bladder cancer cells by reversing EMT through the Wnt/-catenin signaling pathway. Chem Biol Interact. 2020 Apr 1;320:109022. doi: 10.1016/j.cbi.2020.109022. Epub 2020 Feb 27.
4 Thymoquinone induces apoptosis in bladder cancer cell via endoplasmic reticulum stress-dependent mitochondrial pathway. Chem Biol Interact. 2018 Aug 25;292:65-75. doi: 10.1016/j.cbi.2018.06.013. Epub 2018 Jul 2.
5 Thymoquinone suppresses the proliferation of renal cell carcinoma cells via reactive oxygen species-induced apoptosis and reduces cell stemness. Environ Toxicol. 2019 Nov;34(11):1208-1220. doi: 10.1002/tox.22822. Epub 2019 Jul 12.
6 Thymoquinone induces apoptosis of human epidermoid carcinoma A431?cells through ROS-mediated suppression of STAT3. Chem Biol Interact. 2019 Oct 1;312:108799. doi: 10.1016/j.cbi.2019.108799. Epub 2019 Aug 18.
7 Erk phosphorylation reduces the thymoquinone toxicity in human hepatocarcinoma. Environ Toxicol. 2021 Oct;36(10):1990-1998. doi: 10.1002/tox.23317. Epub 2021 Jun 26.