Summary

IMPPAT Phytochemical identifier: IMPHY011352

Phytochemical name: Ergotamine

Synonymous chemical names:
ergotamine

External chemical identifiers:
CID:8223, ChEMBL:CHEMBL442, ChEBI:64318, ZINC:ZINC000052955754, FDASRS:PR834Q503T, SureChEMBL:SCHEMBL1483

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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(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O

InChI:
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

InChIKey:
XCGSFFUVFURLIX-VFGNJEKYSA-N

DeepSMILES:
O=C[C@H]CNC)[C@H]C=C6)cccccc6cC%10)c[nH]5))))))))))))))N[C@]C)O[C@@]NC5=O))[C@@H]Ccccccc6)))))))C=O)N[C@H]6CCC5))))))))O

Functional groups:
CN(C)C, CN(C)C(C)=O, C[C@@]1(NC(C)=O)O[C@](C)(O)N(C)C1=O, cC(C)=CC, c[nH]c

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(NC1OC2C3CCCN3C(=O)C(Cc3ccccc3)N2C1=O)C1C=C2c3cccc4[nH]cc(c34)CC2NC1

Scaffold Graph/Node level:
OC(NC1OC2C3CCCN3C(O)C(CC3CCCCC3)N2C1O)C1CNC2CC3CNC4CCCC(C2C1)C34

Scaffold Graph level:
CC(CC1CC2C3CCCC3C(C)C(CC3CCCCC3)C2C1C)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: 0.963

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Chemical structure download