Compound: artemisinin
SMILES: O=C1O[C@@H]2O[C@@]3(OO[C@@]24[C@H]([C@H](C)CC[C@H]4[C@H]1C)CC3)C
InChIKey: BLUAFEHZUWYNDE-NNWCWBAJSA-N
Synonyms: artemisinin, 63968-64-9, Qinghaosu, Arteannuin, Huanghuahaosu, (+)-Artemisinin, Artemisinine, Artemisininum, Artemisinina, GNF-Pf-5341, 9RMU91N5K2, DTXSID2040652, CHEBI:223316, NSC-369397, (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one, DTXCID40819890, quinghaosu, qing hao su, 2-azanyl-5-methylsulfanyl-pentanoic acid, 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, (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecan-10-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, RefChem:5566, P01BE01, (3R,5AS,6R,8AS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one, 700-290-5, Artemisine, Artemisinin [INN], MFCD00081057, (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one, Qing Hau SU, Qinghosu, Quing Hau Sau, (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, Qinghaosu [Chinese], Artemisinine [French], Artemisininum [Latin], Artemisinina [Spanish], (+)-Arteannuin, Qing Hau Sau [Chinese], (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)-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, SMR000578089, SR-01000802560, NSC 369397, artemizinin, BRN 4194670, UNII-9RMU91N5K2, Artesin, Arteannuin;, Qinghaosu;, NCGC00160207-01, (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-one, (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12H)-one, Artemisinin; (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, CAS-63968-64-9, (+/-)-Artemisinin, Artemisinin (Standard), Spectrum_001351, ARTEMISININ [MI], Prestwick0_000498, Prestwick1_000498, Prestwick2_000498, Prestwick3_000498, Spectrum2_001512, Spectrum3_001549, Spectrum4_000721, Spectrum5_001098, EC 700-290-5, ARTEMISININ [MART.], SCHEMBL60304, ARTEMISININ [USP-RS], ARTEMISININ [WHO-DD], ARTEMISININ [WHO-IP], BSPBio_000395, BSPBio_002998, KBioGR_000982, KBioSS_001831, (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epox12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, MLS001097650, MLS001304036, MLS002153846, DivK1c_000656, SPBio_001583, SPBio_002316, BPBio1_000435, CHEMBL269671, GTPL9954, HY-B0094R, KBio1_000656, KBio2_001831, KBio2_004399, KBio2_006967, KBio3_002498, NINDS_000656, DTXSID501045125, GLXC-06703, HMS2090I17, HMS2096D17, HMS2267N09, HMS3269L13, HMS3413P13, HMS3677P13, HMS3713D17, Pharmakon1600-01503042, (4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one, HY-B0094, Tox21_111750, ARTEMISININUM [WHO-IP LATIN], BDBM50088447, EBC-11176, HB1115, MSK001538, NSC758216, AKOS024457231, Tox21_111750_1, CCG-220498, CS-1794, DB13132, FA09640, LMPR0103190003, NSC-758216, IDI1_000656, NCGC00161634-06, NCGC00161634-18, 119241-68-8, 3,12-Epoxy-12H-pyranol(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3-alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12aR*)-(+)-, AS-12692, SY057423, NS00010623, S1282, EN300-7390753, Q426921, SR-01000802560-2, SR-01000802560-3, SR-01000802560-4, BRD-K13112821-001-08-3, BRD-K13112821-001-14-1, BRD-K13112821-001-17-4, 2AB44F63-5D0F-424A-AA3F-24062F9C1CED, 3,12-epoxy-12h-pyranol(4,3-j)-1,2-benzodioxepin-10(3h)-one,octahydro-3,6,9-tri, (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-Trimethyloctahydro-12H-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one, (3R,5AS,6R,8AS,9R,12S,12AR)-3,6,9-TRIMETHYLOCTAHYDRO-3,12-EPOXYPYRANO(4,3-J )-1,2-BENZODIOXEPIN-10(3H)-ONE
Theoretical properties:
molecular_formula: C15H22O5
molecular_weight: 282.33 g/mol
exact_mass: 282.14672380 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 0
heavy_atom_count: 20
topological_polar_surface_area: 54 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "(+)-artemisinin is a sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria. It has a role as an antimalarial and a plant metabolite. It is an organic peroxide and a sesquiterpene lactone.", "chebi": "A sesquiterpene lactone obtained from sweet wormwood, <em>Artemisia annua</em>, which is used as an antimalarial for the treatment of multi-drug resistant strains of <em>falciparum</em> malaria.", "chembl": "ARTEMISININ is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.", "wikipedia": "Artemisinin () and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum. It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery. Artemisinin-based combination therapies (ACTs) have become standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium. Artemisinin can be extracted from the herb Artemisia annua (sweet wormwood), which is used in traditional Chinese medicine. Alternatively, it can be prepared by a semi-synthetic method from a precursor compound that can be produced using a genetically engineered yeast, which is much more efficient than extraction from the plant.\nArtemisinin and its derivatives are all sesquiterpene lactones containing an unusual peroxide bridge. This endoperoxide 1,2,4-trioxane ring is responsible for their antimalarial properties. Few other natural compounds with such a peroxide bridge are known.\nArtemisinin and its derivatives have been used for the treatment of malarial and parasitic worm (helminth) infections. Advantages of such treatments over other anti-parasitics include faster parasite elimination and broader efficacy across the parasite life-cycle; disadvantages include their low bioavailability, poor pharmacokinetic properties, and high cost. Moreover, use of the drug by itself as a monotherapy is explicitly discouraged by the World Health Organization, as there have been signs that malarial parasites are developing resistance to the drug. Combination therapies, featuring artemisinin or its derivatives alongside some other antimalarial drug, constitute the contemporary standard-of-care treatment regimen for malaria.\n\n"}