Summary

IMPPAT Phytochemical identifier: IMPHY008124

Phytochemical name: Ergotoxine

Synonymous chemical names:
ergotoxine

External chemical identifiers:
CID:3084035, FDASRS:13GR36R05G, SureChEMBL:SCHEMBL3009864

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Chemical structure information

SMILES:
O=C([C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)N[C@@]1(O[C@@]2(N(C1=O)CC(=O)N1[C@H]2CCC1)O)C(C)C

InChI:
InChI=1S/C28H33N5O5/c1-15(2)27(26(36)33-14-23(34)32-9-5-8-22(32)28(33,37)38-27)30-25(35)17-10-19-18-6-4-7-20-24(18)16(12-29-20)11-21(19)31(3)13-17/h4,6-7,10,12,15,17,21-22,29,37H,5,8-9,11,13-14H2,1-3H3,(H,30,35)/t17-,21-,22+,27-,28+/m1/s1

InChIKey:
XLMJRFCCCWFQRE-SJRQCXNHSA-N

DeepSMILES:
O=C[C@H]CNC)[C@H]C=C6)cccccc6cC%10)c[nH]5))))))))))))))N[C@@]O[C@@]NC5=O))CC=O)N[C@H]6CCC5))))))))O)))CC)C

Functional groups:
CC(=O)N(C)C, CN(C)C, CN1C(=O)[C@](C)(NC(C)=O)O[C@]1(C)O, cC(C)=CC, c[nH]c

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(NC1OC2C3CCCN3C(=O)CN2C1=O)C1C=C2c3cccc4[nH]cc(c34)CC2NC1

Scaffold Graph/Node level:
OC(NC1OC2C3CCCN3C(O)CN2C1O)C1CNC2CC3CNC4CCCC(C2C1)C34

Scaffold Graph level:
CC(CC1CC2C(CC(C)C3CCCC32)C1C)C1CCC2CC3CCC4CCCC(C2C1)C43

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Alkaloids and derivatives

ClassyFire Class: Ergoline and derivatives

ClassyFire Subclass: Lysergic acids and derivatives

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Tryptophan alkaloids

NP Classifier Class: Ergot alkaloids

NP-Likeness score: 1.206

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Chemical structure download