Natural Product (NP) Details

General Information of the NP (ID: NP3247)
Name
Artemisinin
Synonyms
Arteannuin; Artemisine; Artemisinina; Artemisinine; Artemisininum; Artesin; Huanghuahaosu; Qinghaosu; Qinghosu; Quinghaosu; Artemisinin [INN]; Artemisinina [Spanish]; Artemisinine [French]; Artemisininum [Latin]; Qing Hau SU; Qing Hau Sau; Qing Hau Sau [Chinese]; Qinghaosu [Chinese]; Quing Hau Sau; Artemisinin (INN); Coartem, Artemisinin; Artemisia annua L., extract; GNF-PF-5671; GNF-Pf-5341; Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one; (+)-Arteannuin; (+)-Artemisinin; (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one; (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one; (5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one; 1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one; 3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one
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Species Origin Artemisia annua ...     Click to Show/Hide
Artemisia annua
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Artemisia
Species: Artemisia annua
Disease Malaria [ICD-11: 1F40] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C15H22O5
PubChem CID
68827
Canonical SMILES
CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C
InChI
1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
InChIKey
BLUAFEHZUWYNDE-NNWCWBAJSA-N
CAS Number
CAS 63968-64-9
Herb ID
HBIN016960
SymMap ID
SMIT08863
TCMSP ID
MOL007424
TTD Drug ID
D0S3WH
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          25-methoxyl-dammarane-3beta, 12beta, 20-triol      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 [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression PRSS50  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
ER7530 Breast cancer Homo sapiens
                    Experimental
                    Result(s)		 25-methoxyl-dammarane-3beta, 12beta, 20-triol and artemisinin synergistically inhibit MDA-MB-231 cell proliferation through downregulation of testes-specific protease 50 (TSP50) expression.
          Oxaliplatin      Colorectal 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 BIRC5  Molecule Info 
Pathway MAP
Down-regulation Expression CTNNB1  Molecule Info 
Pathway MAP
Down-regulation Expression MYC  Molecule Info 
Pathway MAP
                    In-vitro Model Eca-109 CVCL_6898 Esophageal squamous cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination treatment with artemisinin and oxaliplatin inhibits tumorigenesis in esophageal cancer EC109 cell through Wnt/beta-catenin signaling pathway.
          Halofuginone      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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1B  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
SW480 CVCL_0546 Colon adenocarcinoma Homo sapiens
SW620 CVCL_0547 Colon adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
A-375 CVCL_0132 Amelanotic melanoma Homo sapiens
MGC-803 CVCL_5334 Gastric mucinous adenocarcinoma Homo sapiens
Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
Hep 3B2.1-7 CVCL_0326 Childhood hepatocellular carcinoma Homo sapiens
                    In-vivo Model HCT116 cells (5*106 cells per mouse) were suspended in PBS and inoculated subcutaneously into the left flank of each female BALB/c nude mice.
                    Experimental
                    Result(s)		 Halofuginone and artemisinin synergistically arrest cancer cells at the G1/G0 phase by upregulating p21Cip1 and p27Kip1.
          Sodium butyrate      Acute myeloid leukemia     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
                    Biological
                    Regulation		 Up-regulation Apoptosis
                    In-vitro Model MOLT-4 CVCL_0013 Adult T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 DHA in combination with butyric acid acts synergistically at low doses.
Target and Pathway
Target(s) Plasmodium dihydroorotate dehydrogenase (Malaria DHOdehase)  Molecule Info  [1]
Sarcoplasmic/endoplasmic reticulum calcium ATPase (ATP2A)  Molecule Info  [1]
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 Metabolic pathways
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Reactome Pyrimidine biosynthesis Click to Show/Hide
WikiPathways Metabolism of nucleotides Click to Show/Hide
References
Reference 1 The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
Reference 2 25-methoxyl-dammarane-3beta, 12beta, 20-triol and artemisinin synergistically inhibit MDA-MB-231 cell proliferation through downregulation of testes-specific protease 50 (TSP50) expression. Tumour Biol. 2016 Sep;37(9):11805-11813.
Reference 3 Combination treatment with artemisinin and oxaliplatin inhibits tumorigenesis in esophageal cancer EC109 cell through Wnt/beta-catenin signaling pathway. Thorac Cancer. 2020 Aug;11(8):2316-2324.
Reference 4 Halofuginone and artemisinin synergistically arrest cancer cells at the G1/G0 phase by upregulating p21Cip1 and p27Kip1. Oncotarget. 2016 Aug 2;7(31):50302-50314.
Reference 5 Synergistic cytotoxicity of artemisinin and sodium butyrate on human cancer cells. Anticancer Res. Nov-Dec 2005;25(6B):4325-31.
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