Summary

IMPPAT Phytochemical identifier: IMPPAT3_PHYID005080

Phytochemical name: Monocrotaline

Synonymous chemical names:
crotaline, Monocrotaline, pyrrolizidine alkaloid, monocrotaline

External chemical identifiers:
CID:CID_9415, ChEMBL:CHEMBL521035, ChEBI:CHEBI:6980, ZINC:ZINC000053195720, FDASRS:73077K8HYV, SureChEMBL:SCHEMBL164486, MolPort-001-742-605

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Chemical structure information

SMILES:
O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O

InChI:
InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

InChIKey:
QVCMHGGNRFRMAD-XFGHUUIASA-N

DeepSMILES:
O=CO[C@@H]CCN[C@@H]5C=CC5))COC=O)[C@][C@][C@H]%14C))C)O))C)O

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

Link to spectral information:
MSBNK-NaToxAq-NA002259, MSBNK-NaToxAq-NA002258, MSBNK-NaToxAq-NA002257, MSBNK-NaToxAq-NA002256, MSBNK-NaToxAq-NA002255, MSBNK-NaToxAq-NA000748, MSBNK-NaToxAq-NA000707, MSBNK-NaToxAq-NA000746, MSBNK-NaToxAq-NA000745, MSBNK-NaToxAq-NA000709, MSBNK-NaToxAq-NA000708, MSBNK-NaToxAq-NA002652, MSBNK-NaToxAq-NA000747, MSBNK-NaToxAq-NA002653, MSBNK-NaToxAq-NA003402, MSBNK-NaToxAq-NA002655, MSBNK-NaToxAq-NA002656, MSBNK-NaToxAq-NA003034, MSBNK-NaToxAq-NA003035, MSBNK-NaToxAq-NA003036, MSBNK-NaToxAq-NA003037, MSBNK-NaToxAq-NA003038, MSBNK-NaToxAq-NA003399, MSBNK-NaToxAq-NA003400, MSBNK-NaToxAq-NA003401, MSBNK-NaToxAq-NA003403, MSBNK-Washington_State_Univ-BML81705, MSBNK-Washington_State_Univ-BML81706, MSBNK-Washington_State_Univ-BML81707, MSBNK-NaToxAq-NA002654, MSBNK-NaToxAq-NA000706, MSBNK-NaToxAq-NA000663, MSBNK-NaToxAq-NA000662, MSBNK-NaToxAq-NA000411, MSBNK-NaToxAq-NA000412, MSBNK-NaToxAq-NA000413, MSBNK-NaToxAq-NA000414, MSBNK-NaToxAq-NA000705, MSBNK-NaToxAq-NA000461, MSBNK-NaToxAq-NA000462, MSBNK-NaToxAq-NA000463, MSBNK-NaToxAq-NA000464, MSBNK-NaToxAq-NA000465, MSBNK-NaToxAq-NA000511, MSBNK-NaToxAq-NA000512, MSBNK-NaToxAq-NA000513, MSBNK-NaToxAq-NA000514, MSBNK-NaToxAq-NA000415, MSBNK-NaToxAq-NA000561, MSBNK-NaToxAq-NA000515, MSBNK-NaToxAq-NA000661, MSBNK-NaToxAq-NA000660, MSBNK-NaToxAq-NA000615, MSBNK-NaToxAq-NA000614, MSBNK-NaToxAq-NA000613, MSBNK-NaToxAq-NA000659, MSBNK-NaToxAq-NA000611, MSBNK-NaToxAq-NA000565, MSBNK-NaToxAq-NA000564, MSBNK-NaToxAq-NA000563, MSBNK-NaToxAq-NA000562, MSBNK-NaToxAq-NA000612

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1CCCC(=O)OC2CCN3CC=C(CO1)C23

Scaffold Graph/Node level:
OC1CCCC(O)OC2CCN3CCC(CO1)C23

Scaffold Graph level:
CC1CCCC(C)CC2CCC3CCC(CC1)C32

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Organoheterocyclic compounds

ClassyFire Class: Pyrrolizines

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Ornithine alkaloids

NP Classifier Class: Pyrrolizidine alkaloids

NP-Likeness score: 2.65

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Chemical structure download