(1S,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

• ChemBase ID: 72606
• Molecular Formular: C15H22O5
• Molecular Mass: 282.33218
• Monoisotopic Mass: 282.1467238
• SMILES: [C@]12(O[C@@H]3[C@]4([C@@H](CC1)[C@@H](CC[C@H]4[C@H](C(=O)O3)C)C)OO2)C
• Canonical SMILES: O=C1O[C@@H]2O[C@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
• InChI: 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-DKGJTOOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,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; (1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• IUPAC Traditional name: (1S,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; (1S,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,^1^3.0^8,^1^3]hexadecan-10-one
• Synonyms: Coartem; Artemisinin; (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; Arteannuin; Qinghaosu; Qing Hau Sau; Artemisinin

Database IDs

• CAS Number: 63968-64-9
• PubChem SID: 162037531
• PubChem CID: 9838675

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.114058
• LogD (pH = 7.4): 3.114058
• Log P: 3.114058
• Molar Refractivity: 68.6817 cm^3
• Polarizability: 28.359936 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Cryst.

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: Inhibitor of PfATP6, a SERCA-type enzyme; Reactive oxygen radicals producer

Product Information

• Purity: 98.5
• Salt Data: Free Base
• Biological Source: Constit. of Artemisia annua (Qinghaosu)
• Application(s): Antimalarial agent; Shows advantages for use against drug-resistant malarial strains

DETAILS

Selleck Chemicals - S1282

Research Area: Infection
Biological Activity:
Artemisinin is a drug used to treat multi-drug resistant strains of falciparum malaria (as well as increasingly vivax malaria). The compound is isolated from the plant Artemisia annua, a herb described in Chinese traditional medicine, though it is usually chemically modified and combined with other medications. The drug is also being studied as a treatment for cancer. [1]

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