Summary

IMPPAT Phytochemical identifier: IMPHY010731

Phytochemical name: 5(S),9(S),10(S)-15,16-Epoxycleroda-3,8,13(16),14-tetraene-19,18:20,12(S)-diolactone (swassin)

Synonymous chemical names:
plaunolide, swassin

External chemical identifiers:
CID:91741938, ZINC:ZINC000015155119

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Chemical structure information

SMILES:
O=C1OC[C@@]23C1=CCC[C@@H]3[C@]1(C(=C)CC2)C[C@H](OC1=O)c1cocc1

InChI:
InChI=1S/C20H20O5/c1-12-5-7-19-11-24-17(21)14(19)3-2-4-16(19)20(12)9-15(25-18(20)22)13-6-8-23-10-13/h3,6,8,10,15-16H,1-2,4-5,7,9,11H2/t15-,16-,19+,20+/m0/s1

InChIKey:
WQEZWMOABWIAIU-XAMWDVODSA-N

DeepSMILES:
O=COC[C@]C5=CCC[C@@H]6[C@]C=C)CC%10)))C[C@H]OC5=O)))ccocc5

Functional groups:
C=C(C)C, CC=C1CCOC1=O, COC(C)=O, coc

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C=C1CCC23COC(=O)C2=CCCC3C12CC(c1ccoc1)OC2=O

Scaffold Graph/Node level:
CC1CCC23COC(O)C2CCCC3C12CC(C1CCOC1)OC2O

Scaffold Graph level:
CC1CCC23CCC(C)C4(CC(C5CCCC5)CC4C)C2CCCC13

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Terpene lactones

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Diterpenoids

NP Classifier Class: Colensane and Clerodane diterpenoids

NP-Likeness score: 3.342

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Chemical structure download