This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Thymoquinone
- DrugBank Accession Number
- DB16447
- Background
Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Thymoquinone (DB16447)
- Weight
- Average: 164.204
Monoisotopic: 164.083729626 - Chemical Formula
- C10H12O2
- Synonyms
- 2-Isopropyl-5-methyl-p-benzoquinone
- p-Cymene-2,5-dione
- p-Mentha-3,6-diene-2,5-dione
- Thymoquinon
- External IDs
- NSC-2228
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial. It is able to induce apoptosis, regulate pro- and anti- apopotitic genes, and inhibit cancer metastasis through JNK and p38 activation. Its anti-inflammatory effects are attributed to its inhibition of inflammatory cytokines and processes, including pathways associated with 5-LO, COX, and PGD2.
Target Actions Organism ACellular tumor antigen p53 inhibitorHumans AApoptosis regulator Bcl-2 inhibitorHumans AApoptosis regulator BAX inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- O60IE26NUF
- CAS number
- 490-91-5
- InChI Key
- KEQHJBNSCLWCAE-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
- IUPAC Name
- 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
- SMILES
- CC(C)C1=CC(=O)C(C)=CC1=O
References
- General References
- Shaterzadeh-Yazdi H, Noorbakhsh MF, Hayati F, Samarghandian S, Farkhondeh T: Immunomodulatory and Anti-inflammatory Effects of Thymoquinone. Cardiovasc Hematol Disord Drug Targets. 2018;18(1):52-60. doi: 10.2174/1871529X18666180212114816. [Article]
- Imran M, Rauf A, Khan IA, Shahbaz M, Qaisrani TB, Fatmawati S, Abu-Izneid T, Imran A, Rahman KU, Gondal TA: Thymoquinone: A novel strategy to combat cancer: A review. Biomed Pharmacother. 2018 Oct;106:390-402. doi: 10.1016/j.biopha.2018.06.159. Epub 2018 Jul 11. [Article]
- Darakhshan S, Bidmeshki Pour A, Hosseinzadeh Colagar A, Sisakhtnezhad S: Thymoquinone and its therapeutic potentials. Pharmacol Res. 2015 May-Jun;95-96:138-58. doi: 10.1016/j.phrs.2015.03.011. Epub 2015 Mar 28. [Article]
- Velagapudi R, El-Bakoush A, Lepiarz I, Ogunrinade F, Olajide OA: AMPK and SIRT1 activation contribute to inhibition of neuroinflammation by thymoquinone in BV2 microglia. Mol Cell Biochem. 2017 Nov;435(1-2):149-162. doi: 10.1007/s11010-017-3064-3. Epub 2017 May 27. [Article]
- Gholamnezhad Z, Havakhah S, Boskabady MH: Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review. J Ethnopharmacol. 2016 Aug 22;190:372-86. doi: 10.1016/j.jep.2016.06.061. Epub 2016 Jun 27. [Article]
- External Links
- Human Metabolome Database
- HMDB0034732
- ChemSpider
- 9861
- BindingDB
- 166686
- ChEBI
- 113532
- ChEMBL
- CHEMBL1672002
- ZINC
- ZINC000000164367
- PDBe Ligand
- IMW
- Wikipedia
- Thymoquinone
- PDB Entries
- 4hco
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Not Yet Recruiting Treatment Chronic Sinusitis / Nasal Polyps 1 somestatus stop reason just information to hide Not Available Not Yet Recruiting Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 somestatus stop reason just information to hide 2 Completed Treatment Premalignant Lesion 1 somestatus stop reason just information to hide 2, 3 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Immunodeficiencies 1 somestatus stop reason just information to hide 2, 3 Completed Treatment Polycystic Ovarian Syndrome (PCOS) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP 2.55 Chemaxon pKa (Strongest Basic) -7.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 48.89 m3·mol-1 Chemaxon Polarizability 17.84 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01ba-0900000000-977b85d2f66fb318a4db Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-ddba2c838c050b3e0f49 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-2900000000-95a143f9792d9e670458 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00r2-7900000000-04c513494ac077a520f1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01dm-9300000000-7c8d3d66f7773d1f080a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-9400000000-005bc2ebaf635085e447 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.9844102 predictedDarkChem Lite v0.1.0 [M-H]- 141.6936102 predictedDarkChem Lite v0.1.0 [M-H]- 141.2028102 predictedDarkChem Lite v0.1.0 [M-H]- 134.61276 predictedDeepCCS 1.0 (2019) [M+H]+ 141.4795102 predictedDarkChem Lite v0.1.0 [M+H]+ 142.2827102 predictedDarkChem Lite v0.1.0 [M+H]+ 142.0733102 predictedDarkChem Lite v0.1.0 [M+H]+ 138.44011 predictedDeepCCS 1.0 (2019) [M+Na]+ 141.4639102 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.2544102 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.64471 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Multifunctional transcription factor that induces cell cycle arrest, DNA repair or apoptosis upon binding to its target DNA sequence (PubMed:11025664, PubMed:12524540, PubMed:12810724, PubMed:15186775, PubMed:15340061, PubMed:17317671, PubMed:17349958, PubMed:19556538, PubMed:20673990, PubMed:20959462, PubMed:22726440, PubMed:24051492, PubMed:24652652, PubMed:9840937, PubMed:35618207, PubMed:36634798, PubMed:38653238). Acts as a tumor suppressor in many tumor types; induces growth arrest or apoptosis depending on the physiological circumstances and cell type (PubMed:11025664, PubMed:12524540, PubMed:12810724, PubMed:15186775, PubMed:15340061, PubMed:17189187, PubMed:17317671, PubMed:17349958, PubMed:19556538, PubMed:20673990, PubMed:20959462, PubMed:22726440, PubMed:24051492, PubMed:24652652, PubMed:9840937, PubMed:38653238). Negatively regulates cell division by controlling expression of a set of genes required for this process (PubMed:11025664, PubMed:12524540, PubMed:12810724, PubMed:15186775, PubMed:15340061, PubMed:17317671, PubMed:17349958, PubMed:19556538, PubMed:20673990, PubMed:20959462, PubMed:22726440, PubMed:24051492, PubMed:24652652, PubMed:9840937). One of the activated genes is an inhibitor of cyclin-dependent kinases. Apoptosis induction seems to be mediated either by stimulation of BAX and FAS antigen expression, or by repression of Bcl-2 expression (PubMed:12524540, PubMed:17189187). Its pro-apoptotic activity is activated via its interaction with PPP1R13B/ASPP1 or TP53BP2/ASPP2 (PubMed:12524540). However, this activity is inhibited when the interaction with PPP1R13B/ASPP1 or TP53BP2/ASPP2 is displaced by PPP1R13L/iASPP (PubMed:12524540). In cooperation with mitochondrial PPIF is involved in activating oxidative stress-induced necrosis; the function is largely independent of transcription. Induces the transcription of long intergenic non-coding RNA p21 (lincRNA-p21) and lincRNA-Mkln1. LincRNA-p21 participates in TP53-dependent transcriptional repression leading to apoptosis and seems to have an effect on cell-cycle regulation. Implicated in Notch signaling cross-over. Prevents CDK7 kinase activity when associated to CAK complex in response to DNA damage, thus stopping cell cycle progression. Isoform 2 enhances the transactivation activity of isoform 1 from some but not all TP53-inducible promoters. Isoform 4 suppresses transactivation activity and impairs growth suppression mediated by isoform 1. Isoform 7 inhibits isoform 1-mediated apoptosis. Regulates the circadian clock by repressing CLOCK-BMAL1-mediated transcriptional activation of PER2 (PubMed:24051492)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- TP53
- Uniprot ID
- P04637
- Uniprot Name
- Cellular tumor antigen p53
- Molecular Weight
- 43652.79 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
- Specific Function
- BH domain binding
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Plays a role in the mitochondrial apoptotic process (PubMed:10772918, PubMed:11060313, PubMed:16113678, PubMed:16199525, PubMed:18948948, PubMed:21199865, PubMed:21458670, PubMed:25609812, PubMed:36361894, PubMed:8358790, PubMed:8521816). Under normal conditions, BAX is largely cytosolic via constant retrotranslocation from mitochondria to the cytosol mediated by BCL2L1/Bcl-xL, which avoids accumulation of toxic BAX levels at the mitochondrial outer membrane (MOM) (PubMed:21458670). Under stress conditions, undergoes a conformation change that causes translocation to the mitochondrion membrane, leading to the release of cytochrome c that then triggers apoptosis (PubMed:10772918, PubMed:11060313, PubMed:16113678, PubMed:16199525, PubMed:18948948, PubMed:21199865, PubMed:21458670, PubMed:25609812, PubMed:8358790, PubMed:8521816). Promotes activation of CASP3, and thereby apoptosis (PubMed:10772918, PubMed:11060313, PubMed:16113678, PubMed:16199525, PubMed:18948948, PubMed:21199865, PubMed:21458670, PubMed:25609812, PubMed:8358790, PubMed:8521816)
- Specific Function
- BH domain binding
- Gene Name
- BAX
- Uniprot ID
- Q07812
- Uniprot Name
- Apoptosis regulator BAX
- Molecular Weight
- 21184.235 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at January 21, 2021 01:31 / Updated at August 27, 2024 19:16