Summary

IMPPAT Phytochemical identifier: IMPHY003763

Phytochemical name: (6aS,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-7-(2-methylpropyl)-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Synonymous chemical names:
ergosinine

External chemical identifiers:
CID:135569

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Chemical structure information

SMILES:
CC(C[C@H]1C(=O)N2CCC[C@H]2[C@]2(N1C(=O)[C@](O2)(C)NC(=O)[C@H]1CN(C)[C@@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)O)C

InChI:
InChI=1S/C30H37N5O5/c1-16(2)11-23-27(37)34-10-6-9-24(34)30(39)35(23)28(38)29(3,40-30)32-26(36)18-12-20-19-7-5-8-21-25(19)17(14-31-21)13-22(20)33(4)15-18/h5,7-8,12,14,16,18,22-24,31,39H,6,9-11,13,15H2,1-4H3,(H,32,36)/t18-,22+,23+,24+,29-,30+/m1/s1

InChIKey:
NESVMZOPWPCFAU-UGTZLQJCSA-N

DeepSMILES:
CCC[C@H]C=O)NCCC[C@H]5[C@]N9C=O)[C@]O5)C)NC=O)[C@H]CNC)[C@@H]C=C6)cccccc6cC%10)c[nH]5)))))))))))))))))))O))))))))))C

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)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: 1.092

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Chemical structure download