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Aspidophytine

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EntityQ4808018· pop 6· linked from 4 articles

Aspidophytine

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Aspidophytine is an indole alkaloid that has attracted significant attention from synthetic chemists. An extract of the cockroach plant, aspidophytine is an insecticidal substance particularly effective against cockroaches. It is one of the two components of the dimer haplophytine.

Chemical data

Formula
C22H26N2O4
Molecular weight
382.5 g/mol
IUPAC name
(1S,4R,12R,16S)-7,8-dimethoxy-5-methyl-17-oxa-5,15-diazahexacyclo[13.4.3.01,16.04,12.06,11.012,16]docosa-2,6(11),7,9-tetraen-18-one
SMILES
CN1[C@@H]2C=C[C@@]34CCCN5[C@]3([C@]2(CC5)C6=C1C(=C(C=C6)OC)OC)OC(=O)C4
InChIKey
QESOHAISGSLAAJ-DHWLSRIRSA-N
XLogP
2.6
Polar surface area
51.2 Ų
H-bond donors
0
H-bond acceptors
6
Formal charge
0

via PubChem

Wikidata facts

Mass
382.189257
Show 4 more facts
chemical formula
C₂₂H₂₆N₂O₄
isomeric SMILES
CN1[C@@H]2C=C[C@@]34CCCN5[C@]3([C@]2(CC5)C6=C1C(=C(C=C6)OC)OC)OC(=O)C4
canonical SMILES
CN1C2C=CC34CCCN5C3(C2(CC5)C6=C1C(=C(C=C6)OC)OC)OC(=O)C4
found in taxon
Haplophyton cimicidum
Sources (2)

via Wikidata · CC0

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Encyclopedic overview

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Contents
  • References

Aspidophytine is an indole alkaloid that has attracted significant attention from synthetic chemists. An extract of the cockroach plant, aspidophytine is an insecticidal substance particularly effective against cockroaches. It is one of the two components of the dimer haplophytine.

In his suicide note, Harvard doctoral student Jason Altom mentioned his stress in attempting to devise a synthetic pathway for the aspidophytine sub-unit of haplophytine as a contributing factor to his psychological breakdown.

Excerpted from Wikipedia’s “Aspidophytine” article, available under the CC BY-SA 4.0 licence.

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