Summary

IMPPAT Phytochemical identifier: IMPHY007003

Phytochemical name: (15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione

Synonymous chemical names:
jacoline

External chemical identifiers:
CID:78358487, ChEBI:136452, ZINC:ZINC000169420762, MolPort-044-754-047

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Chemical structure information

SMILES:
C[C@H]([C@@]1(O)C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3)O

InChI:
InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1

InChIKey:
FMWJEBGSMAOQNN-YLFNNMARSA-N

DeepSMILES:
C[C@H][C@@]O)C[C@@H]C)[C@@]C)O)C=O)OCC=CCN[C@H]5[C@H]OC%15=O)))CC5)))))))))))))))O

Functional groups:
CC(=O)OC, CC=C(C)C, CN(C)C, CO, COC(C)=O

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1CCCCC(=O)OC2CCN3CC=C(CO1)C23

Scaffold Graph/Node level:
OC1CCCCC(O)OC2CCN3CCC(CO1)C23

Scaffold Graph level:
CC1CCCCC(C)CC2CCC3CCC(CC1)C32

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Macrolides and analogues

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Ornithine alkaloids

NP Classifier Class: Pyrrolizidine alkaloids

NP-Likeness score: 2.266

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Chemical structure download