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162791-23-3 molecular structure
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(1S,4S,5R,8S,9R,12R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

ChemBase ID: 160907
Molecular Formular: C15H23NO4
Molecular Mass: 281.34742
Monoisotopic Mass: 281.16270822
SMILES and InChIs

SMILES:
[C@@H]1([C@H]2C34[C@@H](CC1)[C@H](C(=O)N[C@@H]3O[C@@](CC2)(C)OO4)C)C
Canonical SMILES:
O=C1N[C@@H]2O[C@]3(C)CC[C@@H]4C2([C@H]([C@H]1C)CC[C@H]4C)OO3
InChI:
InChI=1S/C15H23NO4/c1-8-4-5-11-9(2)12(17)16-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3,(H,16,17)/t8-,9-,10+,11+,13-,14+,15?/m1/s1
InChIKey:
LSHOKYZGSIIBMK-XRNKLDBLSA-N

Cite this record

CBID:160907 http://www.chembase.cn/molecule-160907.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,4S,5R,8S,9R,12R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
IUPAC Traditional name
(1S,4S,5R,8S,9R,12R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
Synonyms
(3R,5aS,6R,8aS,9R,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-10(3H)-one
(-)-11-Azaartemisinin
11-Azaartemisinin
CAS Number
162791-23-3
PubChem SID
162255042
PubChem CID
71313537

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC A794900 external link Add to cart
PubChem 71313537 external link
Data Source Data ID Price
TRC
A794900 external link Add to cart Please log in.
Data Source Data ID
PubChem 71313537 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 10.632575  H Acceptors
H Donor LogD (pH = 5.5) 2.3848944 
LogD (pH = 7.4) 2.3846724  Log P 2.3848975 
Molar Refractivity 70.6315 cm3 Polarizability 28.783083 Å3
Polar Surface Area 56.79 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 - A794900 external link
A nontoxic analog of Artemisinin for the oral treatment of malaria.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Klayman, D., et al.: Science, 228, 1049 (1985)
  • • Hu, Y., et al.: Bioorg. Chem., 20, 148 (1985)
  • • Avery, M., et al.: J. Med. Chem., 36, 4264 (1985)
  • • Meshnick, S., et al.: Antimicrob. Agents Chemother., 37, 1108 (1985)
  • • Grace, J., et al.: Xenobiotica, 29, 703
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PATENTS

PATENTS

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INTERNET

INTERNET

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