Summary

IMPPAT Phytochemical identifier: IMPHY015492

Phytochemical name: 3-Tigloylazadirachtin

Synonymous chemical names:
azadirachtin, 3-tigloyl

External chemical identifiers:
CID:122232601

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Chemical structure information

SMILES:
C/C=C(/C(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]41CO[C@]([C@H]4[C@]([C@@H]([C@@H]3OC2)OC(=O)/C(=C/C)/C)(C)[C@@]12O[C@@]2(C)[C@H]2C[C@@H]1O[C@H]1[C@]2(O)C=CO1)(O)C(=O)OC)C(=O)OC)C

InChI:
InChI=1S/C40H50O17/c1-10-18(3)28(42)54-22-15-23(53-20(5)41)37(31(44)48-8)16-51-25-26(37)36(22)17-52-39(47,32(45)49-9)30(36)34(6,27(25)56-29(43)19(4)11-2)40-24-14-21(35(40,7)57-40)38(46)12-13-50-33(38)55-24/h10-13,21-27,30,33,46-47H,14-17H2,1-9H3/b18-10+,19-11+/t21-,22+,23-,24+,25-,26-,27-,30+,33+,34-,35+,36+,37+,38+,39+,40+/m1/s1

InChIKey:
FWCTVIBMYQLXBW-ARPQTLQRSA-N

DeepSMILES:
C/C=C/C=O)O[C@H]C[C@@H]OC=O)C)))[C@@][C@H][C@]6CO[C@][C@H]5[C@][C@@H][C@@H]9OC%12)))OC=O)/C=C/C))/C)))))C)[C@]O[C@@]3C)[C@H]C[C@@H]6O[C@H][C@]6O)C=CO5))))))))))))))O)C=O)OC))))))))C=O)OC)))))))))C

Functional groups:
C/C=C(C)C(=O)OC, CC(=O)OC, CO, COC, COC(=O)[C@@](C)(O)OC, COC(C)=O, CO[C@H]1CC=CO1, C[C@@]1(C)O[C@]1(C)C

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C1=CC2C(O1)OC1CC2C2OC12C1CC2OCC3CCCC4(COCC14)C32

Scaffold Graph/Node level:
C1CC2COC3CC(C45OC4C4CC5OC5OCCC54)C4COCC4(C1)C23

Scaffold Graph level:
C1CC2CC3CC(C2C1)C1CC31C1CC2CCC3CCCC4(CCCC14)C32

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Triterpenoids

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Triterpenoids

NP Classifier Class: Limonoids

NP-Likeness score: 3.127

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Chemical structure download