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113472-97-2 molecular structure
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(1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

ChemBase ID: 160819
Molecular Formular: C15H22O5
Molecular Mass: 282.33218
Monoisotopic Mass: 282.1467238
SMILES and InChIs

SMILES:
[C@@H]1([C@H]2[C@@]34[C@@H](CC1)[C@@H](C(=O)O[C@@H]3O[C@](CC2)(C)OO4)C)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-DWIPZSBTSA-N

Cite this record

CBID:160819 http://www.chembase.cn/molecule-160819.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
IUPAC Traditional name
(1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
Synonyms
(3R,5aS,6R,8aS,9S,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
(+)-9-Epiartemisinin
11-epi-Artemisinin
9-epi-Artemisinin
CAS Number
113472-97-2
PubChem SID
162254954
PubChem CID
821423

DATA SOURCES

DATA SOURCES

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Data Source Data ID
TRC A777505 external link Add to cart
PubChem 821423 external link
Data Source Data ID Price
TRC
A777505 external link Add to cart Please log in.
Data Source Data ID
PubChem 821423 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 3.114058  LogD (pH = 7.4) 3.114058 
Log P 3.114058  Molar Refractivity 68.6817 cm3
Polarizability 28.359936 Å3 Polar Surface Area 53.99 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - A777505 external link
A chiral isomer of Artemisinin (A777500), an antimalarial. A metabolite of Artemisitene (A777550).

REFERENCES

REFERENCES

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  • • Orabi, K.Y. et al.: Phytochem., 51, 257 (1999)
  • • Jefford, C.W. et al.: Helv. Chim. Acta, 83, 1239 (1999)
  • • Klayman, D.L., et al.: Science, 228, 1049 (1985;
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PATENTS

PATENTS

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INTERNET

INTERNET

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