Table 2 SMILES codes for Rhazya stricta compounds

M1

Akummidine

COC(=O)C1(CO)C2CC3=C([NH]C4=C3C=CC=C4)C5CC1\C(CN25)=C/C

M2

Antirhine

OCC(C=C)C1CCN2CCC3=C([NH]C4=C3C=CC=C4)C2C1

M3

3-Epi-antirhine

OCC(C=C)C1CCN2CCC3=C([NH]C4=C3C=CC=C4)C2C1

M4

Aspidosespermidine

CCC12CCCN3CCC4(C(CC1)NC5=C4C=CC=C5)C23

M5

Condylocarpine

COC(=O)C1=C2NC3=CC=CC=C3C24CCN5CCC1\C(=C\C)C45

M6

Dihydrocorynantheol

CCC1CN2CCC3=C([NH]C4=CC=CC=C34)C2CC1CCO

M7

Eburnamenine

CCC12CCCN3CCC4=C(C13)[N](C=C2)C5=CC=CC=C45

M8

Eburnamine

CCC12CCCN3CCC4C(C13)[N](C(O)C2)C5=CC=CC=C45

M9

Eburnamonine

CCC12CCCN3CCC4=C(C13)[N](C(=O)C2)C5=CC=CC=C45

M10

Geissoschizine

COC(=O)\C(=C/O)C\1CC2N(CCC3=C2[NH]C4=CC=CC=C34)CC1=C\C

M11

Isositsirikine

COC(=O)C(CO)C\1CC2N(CCC3=C2[NH]C4=CC=CC=C34)CC1=C/C

M12

16-Epi-Z-isositsirikine

COC(=O)C(CO)C\1CC2N(CCC3=C2[NH]C4=CC=CC=C34)CC1=C\C

M13

Leuconalm

CCC12CCCN3C(=O)C=C(C4=CC=CC=C4NC(=O)CC1)C23O

M14

Rhazinliam

CCC12CCC[N]3C=CC(=C13)C4=CC=CC=C4NC(=O)CC2

M15

Tetrahydrosecamine

CCC1CCCN(CCC2=C([NH]C3=CC=CC=C23)C4(CCC(C(=O)OC)C5=C(CCN6CCCC(CC)C6)C7=C

C=CC=C7[N]45)C(=O)OC)C1

M16

Presecamine

CCC1=CCCN(CCC2=C([NH]C3=CC=CC=C23)OC(=O)C4CCC(=C5N(C)C6=C C=CC=C6C45C

CN7CCC=C(CC)C7)C(=O)OC)C1

M17

Sewarine

COC(=O)C1=C2NC3=C(C=C(O)C=C3)C24CCN5C\C(=C\C)C1CC45

M18

Stemmadenine

C\C=C1/CN2CCC1C(C(=O)OCO)C3=C(CC2)C4=CC=CC=C4[N]3C

M19

Strictamine

COC(=O)C1C\2CC3N(CCC14C3=NC5=CC=CC=C45)CC2=C\C

M20

Strictosamide

OCC1OC(OC2OC=C3C(CC4N(CCC5=C4[NH]C6=CC=CC=C56)C3=O)C2C=C)C(O)C(O)C1O

M21

Strictosidine

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C(C=C)C1CC3NCCC4=C3[NH]C5=CC=CC=C45

M22

Taberonine

CCC12CC(=C3NC4=CC=CC=C4C35CCN(CC=C1)C25)C(=O)OC

M23

Tetrahydrlstonine

COC(=O)C1=COC(C)C2CN3CCC4=C([NH]C5=CC=CC=C45)C3CC12

M24

Vallesiachotamine

COC(=O)C1=CN2CCC3=C([NH]C4=CC=CC=C34)C2CC1\C(=C/C)C=O

M25

Aspidospermoise

CCC12CCCN3CCC4(C(CC1)N(C5OC(O)C(=O)C(O)C5O)C6=CC=CC=C46)C23

M26

Bhimbrine

COC(=O)C(CO)C\1CC2N(CCC3=C2[NH]C4=C3C=CC=C4)CC1=C/C

M27

Bhimbrine N-oxide

COC(=O)C(CO)C\1CC2C3=C(CC[N+]2([O-])CC1=C/C)C4=C([NH]3)C=CC=C4

M28

Rhazimine

COC(=O)C12C(CC3(C=NC4=CC=CC=C34)C1=O)N5CCC2\C(C5)=C/C

M29

Rhazimanine

COC(=O)C(CO)C\1CC2N(CCC3=C2[NH]C4=CC=CC=C34)CC1=C\C

M30

Rhazicine

COC(=O)C12C(CC3(C(O)NC4=CC=CC=C34)C1=O)N5CCC2\C(C5)=C\C

M31

Leepacine

COC(=O)C12C3CC4(C(NC5=CC=CC=C45)C6CC1\C(CN36)=C/C)C2=O

M32

2-Methoxy 1-2,dihydrorhazamine

COC1NC2=CC=CC=C2C13CC4N5CCC(\C(C5)=C/C)C4(C(=O)OC)C3=O

M33

HR-1

C\C=C1\C[N+]2([O-])CCC3=C(C2CC1(O)COC(C)=O)[N](C)C4=CC=CC=C34

M34

Vincanicine

COC1=CC=C2C(=C1)NC3=C(C=O)C\4CC5N(CCC235)CC4=C\C

M35

Rhazinaline

COC(=O)C1(C=O)C\2CC3N(CCC14C3=NC5=CC=CC=C45)CC2=C/C

M36

Beta-sitosterol

CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C

M37

Ursolic acid

CC1CCC2(CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(O)=O

M38

Stigmasterol

CCC(\C=C\C(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C

M39

Olenaolic acid

CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1)C(O)=O

M40

Rhazidigenine (rhazidine)

CCC12CCCN(CCC3(O)C(=NC4=CC=CC=C34)CC1)C2

M41

N-methylleuconolam

CCC12CCCN3C(=O)C=C(C4=CC=CC=C4N(C)C(=O)CC1)C23O

M42

(+)-Quebranchamine

CCC12CCCN(CCC3=C(CC1)[NH]C4=CC=CC=C34)C2

M43

Polyneuridine

COC(=O)C1(C=O)C2CC3=C([NH]C4=CC=CC=C34)C5CC1\C(CN25)=C\C

M44

(+)-Vincadiformine

CCC12CCCN3CCC4(C13)C(=C(C2)C(=O)OC)NC5=CC=CC=C45

M45

(−)-Vincadiformine

CCC12CCCN3CCC4(C13)C(=C(C2)C(=O)OC)NC5=CC=CC=C45

M46

Secamine

CCC1=CCCN(CCC2=C([NH]C3=C2C=CC=C3)C4(CCC(C(=O)OC)C5=C (CCN6CCC=C(CC)

C6)C7=CC=CC=C7[N]45)C(=O)OC)C1

M47

Vincadine

CCC12CCCN(CCC3=C([NH]C4=CC=CC=C34)C(C1)C(=O)OC)C2

M48

Bis-strictidine

CCC1=C2C3CC4(CCN2CCC1)C5C=CC=CC5 N=C4C6CC7(CCN8CCCC(=C68)

CC)C3=NC9=C7C=CC=C9

M49

3,14-Dehydrorhazigine

CCC1=CN(CCC1)CCC2C(=NC3=C2C=CC=C3)C4CCC(=C5NC6=C(C=CC=C6) C45C

CN7CC(=CC=C7)CC)C(=O)OC

M50

16-Hydrorhazisidine

CCC1=CCCN(CCC2=C3C(CC(C(O)[N]3C4=C2C=CC=C4)C5=C(CCN6CCCC(=C6)CC)

C7=C([NH]5)C=CC=C7)C(=O)OC)C1

M51

Rhazisidine

CCC1=CCCN(CCC2=C3C(CC4C([N]3C5=C2C=CC=C5)C6=C(CC)C=C CN6C

CC7=C4[NH]C8=C7C=CC=C8)C(=O)OC)C1

M52

Isorhazicine

COC(=O)C12C(CC3(C(O)NC4=C3C=CC=C4)C1=O)N5CCC2\C(C5)=C\C

M53

Rhazigine

CCC1=CCCN(CCC2=C([NH]C3=C2C=CC=C3)C4CCC(=C5NC6=C(C=CC=C6) C45C

CN7CCC=C(CC)C7)C(=O)OC)C1

M54

Strictisidine

COC(=O)C12C3CC4(C1=O)C(=NC5=C4C=CC=C5)C6CC2\C(CN36)=C\C

M55

Strictamine-N-oxide

COC(=O)C1C\2CC3C4=NC5=CC=CC=C5C14CC[N +]3([O-])CC2=C/C

M56

Strictigine

CCC1=C2CCN(CCC23C(=NC4=CC=CC=C34)C=C)C1

M57

Strictine

COC(=O)C1C2CC3 N(CCC4=C3[N]1C5=CC=CC=C45)C=C2C(C)=O

M58

Stricticine

COC(=O)C1=C2NC3=CC=CC=C3C24CCN5CC6(OC6C)C1CC45

M59

Strictalamine

C\C=C1/CN2CCC34C(C=O)C1CC2C3=NC5=CC=CC=C45

M60

1,2-Dehydroaspidospermine

CCC12CCCN3CCC4(C13)C(=NC5=CC=CC=C45)CC2

M61

Tetrahydrosecodine

CCC1CCCN(CCC2=C([NH]C3=CC=CC=C23)C(C)C(=O)OC)C1

M62

Dihydrosecodine

CCC1=CCCN(CCC2=C([NH]C3=CC=CC=C23)C(C)C(=O)OC)C1

M63

Dihydrosecamine

CCC1CCCN(CCC2=C([NH]C3=C2C=CC=C3)C4(CCC(C(=O)OC)C5=C (CCN6CC

C=C(CC)C6)C7=CC=CC=C7[N]45)C(=O)OC)C1

M64

Dihydropresecamine

CCC1CCCN(CCC2=C([NH]C3=CC=CC=C23)OC(=O)C4CCC(=C5 N© C6=CC=C

C=C6C45CCN7CCC=C(CC)C7)C(=O)OC)C1

M65

Tetrahydropresecamine

CCC1CCCN(CCC2=C([NH]C3=CC=CC=C23)OC(=O)C4CCC(=C5 N© C6=CC=C

C=C6C45CCN7CCCC(CC)C7)C(=O)OC)C1

M66

Rhazinol

C\C=C1\CN2CCC34C(CO)C1CC2C3=NC5=CC=CC=C45

M67

Rhazimol

COC(=O)C1(CO)C\2CC3N(CCC14C3=NC5=CC=CC=C45)CC2=C/C

M68

Rhazidigenine-N-oxide

CCC12CCC[N+]([O-])(CCC3(O)C(=NC4=CC=CC=C34)CC1)C2

M69

(−)-16R,21R-Omethyleburmanine

CCC12CCCN3CCC4=C(C13)[N](C(C2)OC)C5=CC=CC=C45

M70

Decarbomethoxy-15,20,16,17-tetrahydrosecodine

CCC1CCCN(CCC2=C(CC)[NH]C3=CC=CC=C23)C1

M71

1,2-Dehydroaspidospermidine-N-oxide

CCC12CCC[N+]3([O–])CCC4(C13)C(=NC5=CC=CC=C45)CC2

M72

Rhazizine

COC(=O)C12OCN3C(O1)C4(CCN5C\C(=C\C)C2CC45)C6=CC=CC=C36

M73

15-Hydroxyvincadifformine

CCC12CC(=C3NC4=CC=CC=C4C35CCN(CCC1O)C25)C(=O)OC

M74

Dihydroburnamenine

CCC12CCCN3CCC4=C(C13)[N](CC2)C5=CC=CC=C45

M75

16s,16′-Decarboxytetrahydrosecamine

CCC1CCCN(CCC2=C([NH]C3=C2C=CC=C3)C4CCC(C(=O)OC)C5=C

(CCN6CCCC(CC)C6)C7=C(C=CC=C7)[N]45)C1

M76

Nor-C-fluorocuraine

C\C=C1\CN2CCC34C2CC1C(=C3NC5=CC=CC=C45)C=O

M77

Strictibine

COC(=O)C1=CC=C2NC3=CC=CC=C3C12