(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-ol

• ChemBase ID: 72936
• Molecular Formular: C15H24O5
• Molecular Mass: 284.34806
• Monoisotopic Mass: 284.16237387
• SMILES: C1C[C@@H]2[C@]34[C@H]([C@@H]1C)CC[C@@](O[C@H]3O[C@H]([C@@H]2C)O)(C)OO4
• Canonical SMILES: O[C@@H]1O[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/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12-,13-,14-,15-/m1/s1
• InChIKey: BJDCWCLMFKKGEE-KDTBHNEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-ol
• IUPAC Traditional name: (1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-ol
• Synonyms: Dihydroartemisinin

Database IDs

• CAS Number: 71939-50-9
• PubChem SID: 162037856
• PubChem CID: 11358077

CALCULATED PROPERTIES

• Acid pKa: 12.114969
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.8382654
• LogD (pH = 7.4): 2.838257
• Log P: 2.8382654
• Molar Refractivity: 69.9093 cm^3
• Polarizability: 28.899292 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2290

Research Area: Infection
Biological Activity:
Dihydroartemisinin (DHA) is a semi-synthetic derivative of artemisinin and isolated from the traditional Chinese herb Artemisia annua. It is the active metabolite of all artemisinin compounds.  It is recommended as the first-line anti-malarial drug with low toxicity. DHA has been shown to possess promising anticancer activities and induce cancer cell death through apoptotic pathways. [1] It is also a drug used to treat malaria. The lactone of artemisinin could selectively be reduced with mild hydride-reducing agents, such as sodium borohydride, potassium borohydride, and lithium borohydride to dihydroartemisinin (a lactol) in over 90% yield. [2]

REFERENCES

• http://en.wikipedia.org/wiki/Dihydroartemisinin