Artemisinin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Artemisinin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Artemisinin?

The molecule Artemisinin presents a molecular formula of C15H22O5 and its IUPAC name is (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.

Artemisinin is a molecule that comes from from the plant Artemisia annua, also known as sweet wormwood. Artemisinin is a natural product that has been used for centuries in Traditional Chinese Medicine to treat fevers. In the 1970s, Chinese scientists discovered that artemisinin is effective in treating malaria..

Artemisinin is thought to work by binding to iron in the body, which is essential for the malaria parasite to survive. This binding of artemisinin to iron results in the production of reactive oxygen species that kill the parasite..

Artemisinin is now considered the most effective treatment for malaria, and is used in combination with other antimalarial drugs. Artemisinin-based combination therapies are the first line of treatment for malaria in most countries..

Despite its efficacy, artemisinin is not without side effects. The most common side effects are gastrointestinal, such as nausea, vomiting, and diarrhea. More serious side effects, such as Stevens-Johnson syndrome, have been reported, but are rare..

Artemisinin is an important tool in the fight against malaria, but it is not a cure. To prevent the spread of this disease, it is important to use artemisinin in combination with other antimalarial drugs, and to take measures to prevent mosquito bites..

3D structure

Cartesian coordinates

Geometry of Artemisinin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Artemisinin BLUAFEHZUWYNDE-NNWCWBAJSA-N chemical compound 2D structure molecule svg
Artemisinin

 

Molecule descriptors

 
IUPAC name(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
InChI codeInChI=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
InChI KeyBLUAFEHZUWYNDE-NNWCWBAJSA-N
SMILESC[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Arteannuin
  • (+)-Artemisinin
  • (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
  • (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-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)-3,6,9-trimethyloctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-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)-3,6,9-trimethyloctahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(12H)-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
  • (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
  • 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
  • 2AB44F63-5D0F-424A-AA3F-24062F9C1CED
  • 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,12S,12aR)-
  • 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*)-(+)-
  • 63968-64-9
  • 968A649
  • 9RMU91N5K2
  • AS-12692
  • Artemesinin
  • Artemisia annua L., extract
  • Artemisine
  • Artemisinin
  • Artemisinina
  • Artemisinine
  • Artemisininum
  • Artesin
  • Astemisinin
  • BCP02096
  • BDBM50088447
  • BPBio1_000435
  • BRN 4194670
  • BSPBio_000395
  • BSPBio_002998
  • CCG-220498
  • CS-1794
  • DB13132
  • DivK1c_000656
  • EC 700-290-5
  • GNF-Pf-5341
  • GTPL9954
  • HMS2090I17
  • HMS2096D17
  • HMS2267N09
  • HMS3269L13
  • HMS3413P13
  • HMS3677P13
  • HMS3713D17
  • HY-B0094
  • Huanghuahaosu
  • IDI1_000656
  • KBio1_000656
  • KBio2_001831
  • KBio2_004399
  • KBio2_006967
  • KBio3_002498
  • KBioGR_000982
  • KBioSS_001831
  • LMPR0103190003
  • MFCD00081057
  • MLS001097650
  • MLS001304036
  • MLS002153846
  • NINDS_000656
  • NSC 369397
  • NSC-369397
  • NSC-758216
  • NSC758216
  • Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
  • Pharmakon1600-01503042
  • Prestwick0_000498
  • Prestwick1_000498
  • Prestwick2_000498
  • Prestwick3_000498
  • Q426921
  • Qing Hau SU
  • Qing Hau Sau
  • Qinghaosu
  • Qinghaosu,Artemisinine
  • Qinghosu
  • Quing Hau Sau
  • S1282
  • SMR000578089
  • SR-01000802560
  • SR-01000802560-2
  • SR-01000802560-3
  • SR-01000802560-4
  • artemisinin
  • artemsinin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC8143788
  • UNII-9RMU91N5K2
  • AKOS024457231
  • BRD-K13112821-001-08-3
  • BRD-K13112821-001-17-4
  • DTXSID2040652
  • CHEMBL269671
  • CHEBI:223316
  • SPBio_001583
  • SPBio_002316
  • SCHEMBL60304
  • Spectrum_001351
  • Spectrum2_001512
  • Spectrum3_001549
  • Spectrum4_000721
  • Spectrum5_001098

Physico-Chemical properties

IUPAC name(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
Molecular formulaC15H22O5
Molecular weight282.332
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity70.38
LogP2.4
Topological polar surface area54.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.