Summary

IMPPAT Phytochemical identifier: IMPHY009492

Phytochemical name: [(1R,10S,12R,13E,14R,16S,17S,18R)-13-ethylidene-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl]

Synonymous chemical names:
raucaffricine

External chemical identifiers:
CID:124389564, ZINC:ZINC000030724319

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Chemical structure information

SMILES:
OC[C@H]1O[C@@H](O[C@@H]2/C(=C/C)/[C@@H]3C[C@@H]4N2[C@@H]2[C@H]3[C@H]([C@@]3(C2)C4=Nc2c3cccc2)OC(=O)C)[C@@H]([C@H]([C@@H]1O)O)O

InChI:
InChI=1S/C27H32N2O8/c1-3-12-13-8-16-23-27(14-6-4-5-7-15(14)28-23)9-17(19(13)24(27)35-11(2)31)29(16)25(12)37-26-22(34)21(33)20(32)18(10-30)36-26/h3-7,13,16-22,24-26,30,32-34H,8-10H2,1-2H3/b12-3+/t13-,16-,17-,18+,19-,20+,21-,22+,24+,25+,26-,27+/m0/s1

InChIKey:
OSJPGOJPRNTSHP-RACSMSOZSA-N

DeepSMILES:
OC[C@H]O[C@@H]O[C@@H]/C=C/C))/[C@@H]C[C@@H]N6[C@@H][C@H]6[C@H][C@@]C5)C7=Ncc5cccc6)))))))))OC=O)C)))))))))))))[C@@H][C@H][C@@H]6O))O))O

Functional groups:
C/C=C(C)[C@@H](O[C@@H](C)OC)N(C)C, CC(=O)OC, CO, cN=C(C)C

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C=C1C2CC3C4=Nc5ccccc5C45CC2C(C5)N3C1OC1CCCCO1

Scaffold Graph/Node level:
CC1C2CC3C4NC5CCCCC5C45CC2C(C5)N3C1OC1CCCCO1

Scaffold Graph level:
CC1C2CC3C(C1CC1CCCCC1)C1CC4(CC21)C1CCCCC1CC34

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Alkaloids and derivatives

ClassyFire Class: Ajmaline-sarpagine alkaloids

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Tryptophan alkaloids

NP Classifier Class: Corynanthe type

NP-Likeness score: 2.567

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Chemical structure download