Natural Product (NP) Details

General Information of the NP (ID: NP6308)
Name
Thymoquinone
Synonyms
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
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Species Origin Nigella sativa ...     Click to Show/Hide
Nigella sativa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Ranunculaceae
Genus: Nigella
Species: Nigella sativa
Disease Oral premalignant Lesion [ICD-11: 2B64] Phase 2 [1]
Structure
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2D MOL

3D MOL

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Formula
C10H12O2
PubChem CID
10281
Canonical SMILES
CC1=CC(=O)C(=CC1=O)C(C)C
InChI
1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
InChIKey
KEQHJBNSCLWCAE-UHFFFAOYSA-N
CAS Number
CAS 490-91-5
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Difluoromethylornithine      African trypanosomiasis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression DNMT1  Molecule Info 
Pathway MAP
Down-regulation Expression HDAC1  Molecule Info 
Pathway MAP
Down-regulation Expression UHRF1  Molecule Info 
Pathway MAP
                    In-vitro Model Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 Thymoquinone and difluoromethylornithine (DFMO) synergistically induce apoptosis of human acute T lymphoblastic leukemia jurkat cells through the modulation of epigenetic pathways.
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
NCI-H146 CVCL_1473 Lung small cell carcinoma Homo sapiens
                    In-vivo Model Xenografts were obtained by injecting NCI-H460 2*106 cells subcutaneously into the right flank of each female SCID mice (age 5-6 weeks old).
                    Experimental
                    Result(s)		 Thymoquinone combined with cisplatin showed synergistic anticancer activity by down-regulating NF-kappaB.
          Temozolomide      Brain cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BECN1  Molecule Info 
Pathway MAP
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
                    Experimental
                    Result(s)		 TQ enhanced the anti-cancer activity of TMZ by inhibition of autophagy at the transcriptional level and decreased the colony-forming ability and NO production of U87MG cell line.
          Bortezomib      Mantle cell lymphoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression COL11A2  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression MKI67  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Down-regulation Expression RELA  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model U266B1 CVCL_0566 Plasma cell myeloma Homo sapiens
NCI-H929 CVCL_1600 Plasma cell myeloma Homo sapiens
KMS-11 CVCL_2989 Plasma cell myeloma Homo sapiens
RPMI-8226 CVCL_0014 Plasma cell myeloma Homo sapiens
                    In-vivo Model Five-week-old athymic nu/nu male Balb/c mice were implanted subcutaneously in the right flank with U266 cells (2 * 106 cells/100 uL of PBS/Matrigel).
                    Experimental
                    Result(s)		 Thymoquinone overcomes chemoresistance and enhances the anticancer effects of bortezomib through abrogation of NF-KappaB regulated gene products in multiple myeloma xenograft mouse model.
          Imatinib      Mantle cell lymphoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Down-regulation Expression ABCG2  Molecule Info 
Pathway MAP
Down-regulation Expression SLC22A1  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    Experimental
                    Result(s)		 TQ potentiates IM efficacy on HCT116 cells via uptake/efflux genes modulation.
          Zoledronic      Mineral excesses     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP7  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Increase DNA fragmentation
                    In-vitro Model PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
DU145 CVCL_0105 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of TQ and ZA resulted in a significant synergistic cytotoxic activity and DNA fragmentation when compared to any single agent alone, in a dose- and time-dependent manner.
          Topotecan      Ovarian cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
                    Experimental
                    Result(s)		 Thymoquinone, when combined with topotecan in noncytotoxic doses, produced synergistic antiproliferative and proapoptotic effects in AML cells.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
Up-regulation Expression DKK1  Molecule Info 
Pathway MAP
Up-regulation Expression GPX1  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
Up-regulation Expression SMAD4  Molecule Info 
Pathway MAP
Up-regulation Expression TGFB1  Molecule Info 
Pathway MAP
Up-regulation Expression TGFBR2  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
Down-regulation Expression WNT1  Molecule Info 
Pathway MAP
                    In-vivo Model For induction of colorectal tumorigenesis, AOM was dissolved in normal saline and injected subcutaneously at a dose of 15 mg/kg, once weekly for 2 weeks.
                    Experimental
                    Result(s)		 Thymoquinone subdues tumor growth and potentiates the chemopreventive effect of 5-fluorouracil on the early stages of colorectal carcinogenesis in rats.
          Cyclophosphamide      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [10]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression FASN  Molecule Info 
Pathway MAP
Down-regulation Expression HER2  Molecule Info 
Pathway MAP
Down-regulation Expression PTEN  Molecule Info 
Pathway MAP
                    In-vitro Model SK-BR-3 CVCL_0033 Breast adenocarcinoma Homo sapiens
MDA-231 Breast cancer Homo sapiens
                    Experimental
                    Result(s)		 TQ can broadly augment the effect of cyclo in breast cancer cases irrespective of Her-2+ or Her-.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [11]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression MKI67  Molecule Info 
Pathway MAP
Up-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model HuT 102 CVCL_3526 Mycosis fungoides and Sezary syndrome Homo sapiens
Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
                    In-vivo Model 7.5 * 106 HuT-102 tumor cells in 100 ul Media:Matrigel (1:1 ratio) were inoculated subcutaneously in the right flank of NOD/SCID mice (6-8 weeks, ~20 g).
                    Experimental
                    Result(s)		 Thymoquinone enhances the anticancer activity of doxorubicin against adult T-cell leukemia in vitro and in vivo through ROS-dependent mechanisms.
          Gemcitabine      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [12]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-xL  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression mTOR  Molecule Info 
Pathway MAP
Down-regulation Expression NOTCH1  Molecule Info 
Pathway MAP
Down-regulation Expression PSMC4  Molecule Info 
Pathway MAP
Up-regulation Expression PTEN  Molecule Info 
Pathway MAP
Down-regulation Expression RELA  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Up-regulation Cytochrome c release
                    In-vitro Model PANC-1 CVCL_0480 Pancreatic ductal adenocarcinoma Homo sapiens
AsPC-1 CVCL_0152 Pancreatic ductal adenocarcinoma Homo sapiens
BxPC-3 CVCL_0186 Pancreatic ductal adenocarcinoma Homo sapiens
                    In-vivo Model PANC-1 cells (1*106 cells/50 ll) were injected into the pancreatic parenchyma of female BALB/c nude mice.
                    Experimental
                    Result(s)		 Thymoquinone pretreatment overcomes the insensitivity and potentiates the antitumor effect of gemcitabine through abrogation of Notch1, PI3K/Akt/mTOR regulated signaling pathways in pancreatic cancer.
          Tamoxifen      Breast cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [13]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 The synergistic effect of TQ and TAM on human breast cancer cell lines showed cell viability reduction as well as apoptosis induction, independent to estrogen.
References
Reference 1 ClinicalTrials.gov (NCT03208790) Clinical and Immunohisochemical Evaluation of Chemopreventive Effect of Thymoquinone on Oral Potentially Malignant Lesions.
Reference 2 Thymoquinone and Difluoromethylornithine (DFMO) Synergistically Induce Apoptosis of Human Acute T Lymphoblastic Leukemia Jurkat Cells Through the Modulation of Epigenetic Pathways. Technol Cancer Res Treat. Jan-Dec 2020;19:1533033820947489.
Reference 3 Thymoquinone and cisplatin as a therapeutic combination in lung cancer: In vitro and in vivo. J Exp Clin Cancer Res. 2010 Jul 1;29(1):87.
Reference 4 Thymoquinone synergistically potentiates temozolomide cytotoxicity through the inhibition of autophagy in U87MG cell line. Iran J Basic Med Sci. 2016 Aug;19(8):890-898.
Reference 5 Thymoquinone overcomes chemoresistance and enhances the anticancer effects of bortezomib through abrogation of NF-KappaB regulated gene products in multiple myeloma xenograft mouse model. Oncotarget. 2014 Feb 15;5(3):634-48.
Reference 6 Thymoquinone chemosensitizes human colorectal cancer cells to imatinib via uptake/efflux genes modulation. Clin Exp Pharmacol Physiol. 2021 Jun;48(6):911-920.
Reference 7 Enhanced cytotoxicity and apoptosis by thymoquinone in combination with zoledronic acid in hormone- and drug-resistant prostate cancer cell lines. J BUON. Oct-Dec 2014;19(4):1055-61.
Reference 8 Antiproliferative and proapoptotic effects of topotecan in combination with thymoquinone on acute myelogenous leukemia. Clin Lymphoma Myeloma Leuk. 2014 Sep;14 Suppl:S46-55.
Reference 9 Thymoquinone subdues tumor growth and potentiates the chemopreventive effect of 5-fluorouracil on the early stages of colorectal carcinogenesis in rats. Drug Des Devel Ther. 2016 Jul 11;10:2239-53.
Reference 10 Thymoquinone Augments Cyclophosphamide-Mediated Inhibition of Cell Proliferation in Breast Cancer Cells. Asian Pac J Cancer Prev. 2019 Apr 29;20(4):1153-1160.
Reference 11 Thymoquinone enhances the anticancer activity of doxorubicin against adult T-cell leukemia in vitro and in vivo through ROS-dependent mechanisms. Life Sci. 2019 Sep 1;232:116628.
Reference 12 Thymoquinone Pretreatment Overcomes the Insensitivity and Potentiates the Antitumor Effect of Gemcitabine Through Abrogation of Notch1, PI3K/Akt/mTOR Regulated Signaling Pathways in Pancreatic Cancer. Dig Dis Sci. 2015 Apr;60(4):1067-80.
Reference 13 Thymoquinone Could Increase The Efficacy of Tamoxifen Induced Apoptosis in Human Breast Cancer Cells: An In Vitro Study. Cell J. Jul-Sep 2016;18(2):245-54.
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