monoterpenoid indole alkaloid (CHEBI:65323)
Definition: A terpenoid indole alkaloid which is biosynthesised from L-tryptophan and diisoprenoid (usually secolaganin) building blocks.
Example SMILES structures:
[H][C@@]12C[C@]3(CN4CC[C@@]56C(Nc7ccccc57)=C(C[C@@]5(CCO[C@@]35[H])[C@]46[H])C(=O)OC)CN3c4c(OC)cccc4[C@@]4(CCN5CC[C@]6([H])OCC[C@]6(C1)[C@@]45[H])[C@]23O
[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCc3c1[nH]c1ccccc31)C2
CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
CCN(CC)CCN1C2=C(C=CC(=C2)OC)C3=C1[C@H]4C[C@H]5[C@H](C[C@H]([C@@H]([C@H]5C(=O)OC)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC)CN4CC3
CCC1=C[C@H]2C[N@@](C1)CCc1c([nH]c3ccccc13)[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N(C)[C@@H]1[C@]22CCN3CC=C[C@](CC)([C@@H]23)[C@@H](OC(C)=O)[C@]1(O)C(=O)OC
O=C1N2[C@@]3([C@@]4([C@]5(N(CC4)C\C(\[C@](C5)(C3=CC1)[H])=C\CO)[H])C=6C2=CC=CC6)[H]
O=C1N2[C@@]3([C@@]4([C@]5(N(CC4)C/C(/[C@](C5)(C3=CC1)[H])=C/CO)[H])C=6C2=CC(=C(C6)OC)OC)[H]
O=C1N2[C@@]3([C@@]4([C@]5([N+](CC4)(C\C(\[C@](C5)(C3=CC1)[H])=C\CO)[O-])[H])C=6C2=CC=CC6)[H]
O=C1N2[C@@]3([C@@]4([C@]5([N+](CC4)(C\C(\[C@](C5)(C3=CC1)[H])=C\CO)[O-])[H])C=6C2=CC(=C(C6)OC)OC)[H]
O=C1N2[C@@]3([C@@]4([C@]5(N(CC4)C\C(\[C@](C5)([C@]3([C@@H](C1)O)[H])[H])=C\CO)[H])C=6C2=CC=CC6)[H]
O=C1N2[C@@]3([C@@]4([C@]5(N(CC4)C\C(\[C@](C5)([C@]3(CC1)[H])[H])=C\CO)O)C=6C2=CC=CC6)[H]
O=C1[C@]23C=4N(C=5C2=CC=CC5)C(=O)C=CC4[C@@](C1)(/C(/CN(CC3)C)=C\CO)[H]
C1[C@@]2(N3CC[C@@]42[C@]5(N(C=6C4=CC=CC6)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])O
C1[C@@]2(N3CC[C@@]42[C@]5(N(C=6C4=CC(=C(C6)OC)OC)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])O
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=CC=C6)=O)[H])[H])[H])[H]
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=C(C(=C6)OC)OC)=O)[H])[H])[H])[H]
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=CC=C6)=O)[H])O)[H])[H]
C1[C@@]2(N3CC[C@@]42[C@]5(N(C=6C4=CC=C(C6)OC)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])[H]
C1[C@@]2(N3CC[C@@]42[C@]5(N(C=6C4=CC(=CC6)OC)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])[H]
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=C(C=C6)O)=O)[H])[H])[H])[H]
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=CC(=C6)O)=O)[H])[H])[H])[H]
[C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN([C@H](C2)O)C)=CCO[C@]5(CC(N4C6=C3C=CC=C6)=O)[H])[H])[H])[H]
C1[C@@]2([N+]3(CC[C@@]42[C@]5(N(C=6C4=CC=CC6)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])[O-])[H]
C1[C@@]2(N3CC[C@@]42[C@]5(N(C=6C4=CC(=C(C6)OC)O)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])[H]
C1[C@@]2(N3C(C[C@@]42[C@]5(N(C=6C4=CC(=C(C6)OC)OC)C(C[C@]7([C@@]5([C@@]1(C(=CCO7)C3)[H])[H])[H])=O)[H])=O)[H]
C(C)[C@@]12[C@]3([C@]4(C=5C(N(C)[C@]4([C@](C(NNC(OCCSSC[C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CC[C@H](NC(=O)C6=CC=C(NCC=7N=C8C(=NC(N)=NC8=O)NC7)C=C6)C(O)=O)=O)CC(O)=O)=O)CCCNC(=N)N)=O)CC(O)=O)=O)CC(O)=O)=O)C(O)=O)=O)=O)(O)[C@@H]1O)[H])=CC(OC)=C([C@]9(C(OC)=O)C%10=C(C=%11C(=CC=CC%11)N%10)CCN%12C[C@](C[C@](C%12)(CC)O)([H])C9)C5)CCN3CC=C2)[H]
C(OC)(=O)C=1[C@]2(C[C@@]3(C4=C(C5=C(N4)C=C(C(=C5)OC)OC)CCN3C[C@]2([C@@H](OC1)C)[H])[H])[H]
C(OC)(=O)[C@H]1[C@]2(C[C@@]3(C4=C(C5=C(N4)C=CC(=C5)OC)CCN3C[C@]2(C[C@H]([C@@H]1OC)OC(=O)C6=CC(OC)=C(C(=C6)OC)OC)[H])[H])[H]
[C@@]123C(=NC4=C1C=CC(=C4)OC)[C@](C[C@]5([C@@]2(N(CC=C5)CC3)[H])CC)(C(=O)OC)O
[C@@]123[C@@H](NC4=C1C=CC=C4)[C@](C[C@]5([C@@H]2N(CC=C5)CC3)CC)(C(=O)OC)O
C/C=C\1/CN2CCC=3C=4C=C(C=CC4NC3C2CC1CCO)O
C=C[C@]1(CN2CCC=3C=4C=C(C=CC4NC3[C@@]2(C[C@@]1(C[C@@]5(C6=C(CCN5C)C7=CC=CC=C7N6)[H])[H])[H])O)[H]
C=C[C@]1(CN2CCC=3C=4C=CC(=CC4NC3[C@@]2(C[C@@]1(C[C@@]5(C6=C(CCN5C)C7=CC=CC=C7N6)[H])[H])[H])O)[H]
COC=1C=CC=2C=3CCN4C[C@@]5(CC[C@@]([C@@]([C@]5(C[C@]4(C3NC2C1)[H])[H])(C(=O)OC)[H])(O)[H])[H]
CC[C@@]12C=CCN3CCC=4C5=CC=CC=C5N(C4[C@]13[H])[C@](C2)(C(=O)OC)O
CC[C@]1(CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(C[C@]5(C6=C(CCN5C)C7=CC=CC=C7N6)[H])[H])[H])[H]
C/C=C\1/CN2[C@](C[C@@]34C5=CC=CC=C5N6C(C=C[C@@]([C@]1(C[C@@]32[H])[H])([C@@]46[H])[H])=O)([C@@]7(C=C8[C@]/9(C[C@]%10([C@@]%11(CCN%10C\C9=C\CO)C%12=CC=CC=C%12N([C@@]8%11[H])C7=O)[H])[H])[H])[H]
C/C=C/1\CN(C)C[C@]2(CC=3C4=CC=CC=C4NC3C(C[C@@]12[H])=O)C(=O)OC
CCC1CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(CC=5C6=C(C=CN5)C7=CC=CC=C7N6)[H])[H]
C=1C(=C(C=C2C1[C@@]34[C@@]5([C@@]6([C@](CC(N25)=O)(OC[C@@H]7[C@]([C@@]6(CC3=O)[H])(O7)CN(CC4)C)[H])[H])[H])OC)OC
C/C=C\1/CN2CC[C@@]3(C4=CC=CC=C4N5C=C([C@]1(C[C@]2([C@]35O)[H])[H])C(=O)OC)O
C/C=C\1/C[N+]=2C=CC=3C=4C=CC=CC4NC3C2CC1CCO
C/C=C\1/C[N+]=2C=CC=3C=4C=CC=CC4NC3C2C[C@@]1(C5=CN6C7=CC=CC=C7[C@]89CCN%10C\C(=C\C)\[C@](C[C@@]8%10[H])([C@@]([C@@H]5O)([C@@]96[H])[H])[H])[H]
CC[C@@]1(CN2CC[C@@]34C5=CC=CC=C5N6[C@]4([C@@](CO[C@]6([C@@]([C@]/7(CC=8C9=C(C=C[N+]8C\C7=C\C)C=%10C=CC=CC%10N9)[H])(C(=O)OC)[H])[H])([C@]1(C[C@@]32[H])[H])[H])[H])[H]
C=C[C@]12C=CCN3CC[C@@]4(C5=CC=CC=C5N=C([C@@]4(C1)[H])O)[C@]23[H]
COC(C1=CO[C@]([C@]2([C@@]1(C[C@@]34C5=C(CCN4C[C@]2(O3)[H])C6=CC=CC=C6N5)[H])[H])(OC7C(C(C(C(CO)O7)O)O)O)[H])=O
CC[C@]1(C[C@@]2(C[C@]3(C4=C(CCN([C@@]13[H])C2=O)C5=CC([C@]6(CC7[C@](CC)(CN(C)C(CC=8C9=CC=CC=C9NC68)[C@]7(C(=O)OC)[H])[H])[H])=C(C=C5N4)OC)C(=O)OC)[H])[H]
CC[C@@]1(C[C@@]2(C[C@@]3(C4=C(CCN(C2)[C@]13[H])C5=CC(=C(C=C5N4)OC)[C@]6(C[C@]7([C@H](CC)CN(C)[C@@](CC=8C9=CC=CC=C9NC86)(C7C(=O)OC)[H])[H])O)C(=O)OC)[H])[H]
CCC=1C=CC2=C3C(CCN2C1)=C4C=CC=CC4=N3
CC(C(C(N1C2=CC=CC=C2[C@]34CCN5C[C@]6([C@@H](C)OC[C@]([C@]6(C[C@@]35O)[H])([C@@]41[H])[H])[H])=O)O)=O
C/C=C(/C=O)\[C@@]1(CC2C3=C(CCN2C)C4=CC=CC=C4N3[C@](C1)(O)[H])[H]
C[C@H]1[C@@]2(CN3CCC=4C5=CC=CC=C5NC4[C@]3(C[C@@]2(C(=CO1)C(=O)OC)[H])[H])[H]
C/C=C\1/CN2CC[C@]34C5=CC=CC=C5N=C4[C@@]2(C[C@@]1(C3(COC(C)=O)C(=O)OC)[H])[H]
CC=1C=CC2=C(C1)C=3CCN4C[C@]5(CC[C@@](C([C@]5(C[C@]4(C3N2)[H])[H])(C(=O)OC)[H])(O)[H])[H]
C/C=C\1/CN2CC[C@@]34C5=CC=CC=C5N6[C@@]([C@]1(C[C@]2([C@@]36OC7=C4C=C8C(=C7O)C(=O)O[C@@]9%10[C@@]%11(C[C@]%12(/C(=C\C)/CN%11CC[C@@]8%10C%13=CC=CC=C%13N9[C@@]%12(C(=O)OC)[H])[H])[H])[H])[H])(C(=O)OC)[H]
C/C=C\1/CN2[C@]3(C[C@@]1(C(CO)(C(=O)OC)[C@@]45C[C@@]2(O[C@@]34NC6=CC=CC=C65)[H])[H])[H]
C/C=C\1/CN(C)[C@]2(CC=3C4=CC=CC=C4NC3[C@](C[C@]1(C2C(=O)OC)[H])(C=5C=CC=6C(CCN)=CNC6C5)[H])[H]
C/C=C\1/C[N@+]2(C)CC[C@@]34C5=CC=CC=C5NC4=C(C=O)[C@]1(C[C@@]32[H])[H]
C=C[C@]1(CN2CC[C@]1(C[C@]2(C3=C(CCO)C4=CC=CC=C4N3)[H])[H])[H]
C/C=C\1/C[N+]2(C)CCC=3C4=CC=CC=C4N5C(CO)[C@]1(C[C@]2(C35)[H])[H]
C/C=C\1/C2CC[N@+]3(CC[C@]4(C5=CC=CC=C5NC4=C2C(=O)OC)[C@@]13[H])[O-]
CC[C@]1(C[C@]2(C[C@]3(C4=C(CCN(C2)C13)C5=CC(=C(C=C5N4)OC)OC)C(=O)OC)[H])[H]
CC[C@@]1(CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(CC=O)[H])[H])[H]
CC[C@@]1(CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(CCO)[H])[H])[H]
C=C[C@]1(CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(/C(=C(\OC)/[H])/C(=O)OC)[H])[H])[H]
C=C[C@]1(CN2CCC=3C4=CC=CC=C4NC3[C@@]2(C[C@@]1(CCO)[H])[H])[H]
CC[C@@]12CC[C@@]34[C@@](CCN(C[C@@]5([C@]1(O5)[H])[H])[C@@]23[H])(C=6C=C(C=CC6N4)[C@]7([C@@]8([C@]([C@@]9(CC)CC(=C%10[C@]%11(CCN7[C@@]9%11[H])C%12=CC=CC=C%12N%10)C(=O)OC)(O8)[H])[H])[H])[H]
C=CC1C2C[C@]3([C@@]45C(C6=CC=CC=C6N4)[C@@](CN3)(O[C@@](C25C(=O)OC)(O[C@]1(O[C@@H]7[C@H]([C@@H]([C@H]([C@H](CO)O7)O)O)O)[H])[H])[H])[H]
C[C@H]1[C@@H]2CN(C)CC[C@@]34C5=CC=CC=C5N[C@]4([C@](CO1)([C@]2(CC3=O)[H])[H])[H]
C/C=C\1/CN2CC[C@]34C5=CC(C=6C=C7C(=CC6OC)[C@]89CCN%10C/C(=C\C)/[C@](CCC8%10N7C)([C@]9(C(=O)OC)[H])[H])=C(C=C5N(C)[C@]4(C2C[C@@]1([C@@]3(C(=O)OC)[H])[H])[H])OC
CC[C@H]1CN(C)[C@]2(CC=3C4=CC=CC=C4NC3C(C[C@@]1([C@@H]2C(=O)OC)[H])=O)[H]
O[C@H]([C@@]1(CN2CC[C@@]34C5=CC=CC=C5NC4=C([C@]1(C[C@@H]32)[H])C(=O)OC)[H])C
CC[C@@]12C[C@]3([C@]4([C@]5(CC)C[C@@]67CC(=C8[C@@](CCN46)(C9=CC=CC=C9N8)[C@@]7(N%10C%11=CC=CC=C%11[C@@]%12(CCN(C[C@@]%13([C@]1(O%13)[H])[H])[C@@]2%12[H])[C@]3%10O5)[H])C(=O)OC)[H])[H]
CC[C@@]1(CN(C)C[C@]2(CC=3C4=CC=CC=C4NC3C(C[C@@]12[H])=O)C(=O)OC)[H]
C/C=C\1/CN(C)[C@@]2(C(=C)[C@]1(CC(C3=C2C4=CC=CC=C4N3)=O)[H])[H]
CCC1=C(CC(=O)OC)[C@](C=2C3=C(C=CN2)C4=CC=CC=C4N3)(O)OC1=O
CC[C@@]1(CN2CC[C@@]34C5=CC=CC=C5N6[C@]4([C@@](CO[C@]6(C7[C@@]/8(C[C@]9(C%10=C(C[C@@]7(N9C\C8=C\C)[H])C%11=CC=CC=C%11N%10)[H])[H])[H])([C@]1(C[C@]32[H])[H])[H])[H])[H]
C/C=C\1/CN2CC[C@@]34CC=5C=C6C(=CC5O[C@@]74[C@@]2(C[C@@]1([C@@](C(=O)OC)(N7C8=CC=CC=C83)[H])[H])[H])N[C@]9%10CC[C@@]%11(CC)CCC[N@+]%10(CC[C@@]69O)C%11
C/C=C\1/CN2CC[C@@]34CC=5C=C6C=7CCN8CCC[C@](CC)(CCC7NC6=CC5O[C@@]94[C@]2(C[C@]1([C@@](C(=O)OC)(N9C%10=CC=CC=C%103)[H])[H])[H])C8
C/C=C\1/CN2CC[C@@]34C5=CC=CC=C5N6[C@@]([C@]1(C[C@]2([C@@]36OC=7C=C8C(=CC7C4=O)[C@@]9(CC[N@+]%10%11CCC[C@](CC)(CC[C@@]9%10N8)C%11)O)[H])[H])(C(=O)OC)[H]
C/C=C\1/C[N+]2(CC[C@@]34CC=5C=C6C(=CC5O[C@@]74[C@@]2(C[C@@]1([C@@](C(=O)OC)(N7C8=CC=CC=C83)[H])[H])[H])N[C@]9%10CC[C@@]%11(CC)CCC[N@+]%10(CC[C@@]69O)C%11)[O-]
CC[C@]12CCCN[C@]1(N3C4=CC=CC=C4C(CCO)=C3CC2)[H]
COC(C1C[C@@]23C=CC(N3CCC4(C5=CC=CC=C5N(C(=O)OC)[C@@]14CC2)C(=O)OC)=O)=O
C/C=C\1/CN(C)CC[C@@]23C4=CC=CC=C4N5[C@]3([C@](CO[C@@H](C5=O)O)([C@]1(CC2=O)[H])[H])[H]
C/C=C\1/CN(C)CC[C@@]23C4=CC=CC=C4N5[C@]3([C@](CO[C@@](C5=O)(OC)[H])([C@]1(CC2=O)[H])[H])[H]
C[C@@H]([C@@]1(C[C@]2(C[C@]3(C4=C(CCN(C2)[C@@]13[H])C=5C=C(C=CC5N4)OC)[H])[H])[H])O
C[C@@]1(C2=CN=CC=C2C[C@]3(C4=C(CC[N@+]13C)C5=CC=CC=C5N4)[H])[H]
OC[C@H]1[C@@]2(N(C=3C([C@@]42[C@H]5N(CC4)C\C(\[C@@]1(C5)[H])=C\C)=CC=CC3)C(=O)C)[H]
C=C[C@]1(CN2CCC=3C=4C=CC(=C([C@@]5(CCCN5C)[H])C4NC3[C@@]2(C[C@@]1(C[C@]6(C7=C(CCN6C)C8=CC=CC=C8N7)[H])[H])[H])O)[H]
C/C=C\1/CN2CC[C@@]34C5=CC=CC=C5N6[C@]4(C(=CC([C@]7(C[C@@]89C%10=CC=CC=C%10N%11C(C=C[C@@]([C@]/%12(C[C@@]8(N7C\C%12=C\C)[H])[H])([C@@]9%11[H])[H])=O)[H])C6=O)[C@]1(C[C@@]32[H])[H])[H]
CC1[C@]2(CN(C)[C@]3(C[C@@]2(C(COC(\C=C\C4=CC=CC=C4)=O)(C(=O)OC)[C@@]56CC(=O)O[C@@]35NC7=CC=CC=C76)[H])[H])O1
CC[C@@]12CCCN3C(C=C(C4=CC=CC=C4NC(CC1)=O)[C@@]23O)=O
CC[C@]1(CN2CC[C@@]34C5=CC=CC=C5N6C[C@@]7(C[C@@]8(C[C@](CC)(N9CC[C@@]%10(C%11=CC=CC=C%11N=C7%10)C89)[H])[H])CC([C@]1(CC32)[H])=C46)[H]
COC=1C=CC2=C(C1)[C@@]34CCN5C(C=C[C@@]65CC[C@]4([C@H]3C6)N2C(=O)OC)=O
C[C@]1(C2=CN=CC=C2C[C@]3(C4=C(CC[N@+]13C)C5=CC=CC=C5N4)[H])[H]
CC[C@]12C=CCN3CC[C@@]4(C5=CC([C@]6(C=C[C@@]7(CC)CC(=C8[C@]9(CCN6[C@@]79[H])C=%10C=CC=C(C%10N8)O)C(=O)OC)[H])=C(C=C5NC4=C(C1)C(=O)OC)O)[C@]23[H]
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