================================================================================
Supporting information for:
Structural Diversity and Chemical Space of Natural Product Substituents Across Different Organism Groups
by Peter Ertl
submitted to J. Nat. Prod. 2026
https://ertlmolecular.com/data/
================================================================================

********** plants
[R]O
[R]C
[R]CO
[R]OC
[R]OC(C)=O
[R]OC1OC(CO)C(O)C(O)C1O
[R]C(O)=O
[R]C(=O)OC
[R]OC1OC(C)C(O)C(O)C1O
[R]C(C)C
[R]c1ccc(O)cc1
[R]COC(C)=O
[R]CC=C(C)C
[R]OC(=O)C(C)=CC
[R]OC1OCC(O)C(O)C1O
[R]C=O
[R]c1ccc(O)c(O)c1
[R]CC
[R]C(C)=C
[R]OC(=O)c1ccccc1
[R]C=C
[R]C(C)(C)O
[R]c1ccoc1
[R]C(C)=O
[R]COC1OC(CO)C(O)C(O)C1O
[R]c1ccccc1
[R]Br
[R]c1ccc(O)c(OC)c1
[R]OC(=O)C(C)CC
[R]C(=O)OC1OC(CO)C(O)C(O)C1O
[R]Cl
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]COC1OC(C)C(O)C(O)C1O
[R]c1ccc(OC)cc1
[R]OC(=O)C(C)C
[R]C1=CC(=O)OC1
[R]OC(=O)C=Cc1ccccc1
[R]CC(=O)OC
[R]COC
[R]COC1OCC(O)C(O)C1O
[R]OC(=O)C=Cc1ccc(O)cc1
[R]C(C)O
[R]OC(=O)C=Cc1ccc(O)c(O)c1
[R]C1OC(CO)C(O)C(O)C1O
[R]c2ccc1OCOc1c2
[R]COC(=O)C=Cc1ccc(O)cc1
[R]CC=C
[R]N
[R]OC(=O)CC(C)C
[R]CCC=C(C)C
[R]OC1OC(C(O)=O)C(O)C(O)C1O
[R]CC=C(C)CCC=C(C)C
[R]c1cc(OC)c(O)c(OC)c1
[R]OC1OCC(O)(CO)C1O
[R]OC(=O)C=Cc1ccc(O)c(OC)c1
[R]c1ccc(OC)c(OC)c1
[R]C(C)CCC=C(C)C
[R]CC(C)C
[R]CC(O)=O
[R]c1cc(O)c(O)c(O)c1
[R]CCC(O)=O
[R]c1cc(O)cc(O)c1
[R]OS(O)(=O)=O
[R]C=C(C)C
[R]COC(=O)c1ccccc1
[R]c1ccc(O)cc1O
[R]C(C)CC
[R]Cc1ccc(O)cc1
[R]Cc1ccccc1
[R]OC1OC(CO)C(O)C1O
[R]CCCCC
[R]OC1CC(OC)C(O)C(C)O1
[R]OCC
[R]OC(=O)C=C(C)C
[R]c1ccc(OC)c(O)c1
[R]C1(C)CCC(C(C)(C)O)O1
[R]OC(=O)C(C)=C
[R]OC1OC(COC(C)=O)C(O)C(O)C1O
[R]CCc1ccoc1
[R]CCO
[R]COC(=O)C=Cc1ccc(O)c(OC)c1
[R]COC(=O)c1cc(O)c(O)c(O)c1
[R]CC(C)=O
[R]COC(=O)C=Cc1ccc(O)c(O)c1
[R]C(=O)C(C)C
[R]OC(=O)c1cccnc1
[R]COC1OCC(O)(CO)C1O
[R]c1cc(OC)c(OC)c(OC)c1
[R]OCCc1ccc(O)c(O)c1
[R]COC(=O)CC(O)=O
[R]C(C)(C)C=C
[R]C(C)CCC(CC)C(C)C
[R]CCCO
[R]CC=C(C)C=C
[R]OO
[R]C(=O)C(C)CC
[R]c1ccc(=O)oc1
[R]N(C)C
[R]C(=O)C=Cc1ccc(O)cc1
[R]C(C)N(C)C
********** fungi
[R]O
[R]C
[R]OC
[R]CO
[R]OC(C)=O
[R]C(O)=O
[R]C(C)C
[R]C(=O)OC
[R]Cl
[R]C=O
[R]OC1OC(CO)C(O)C(O)C1O
[R]Cc1ccccc1
[R]CC=C(C)C
[R]CC(C)C
[R]C(C)(C)O
[R]C(C)=O
[R]c1ccc(O)cc1
[R]C(C)=C
[R]COC(C)=O
[R]CC
[R]C(C)CC
[R]C(C)(C)C=C
[R]C(C)O
[R]c1ccccc1
[R]C=C
[R]Cc1c[nH]c2ccccc12
[R]C=CC
[R]OC1OC(C)C(O)C(O)C1O
[R]CCC
[R]C(C)C=CC(C)C(C)C
[R]N
[R]CCCCC
[R]Cc1ccc(O)cc1
[R]Br
[R]OC(=O)c1ccccc1
[R]c1ccc(O)c(O)c1
[R]CC(O)=O
[R]SC
[R]CC(C)O
[R]CCO
[R]c1ccc(OC)cc1
[R]OC1OCC(O)C(O)C1O
[R]COC
[R]C=C(C)C
[R]CCC(O)=O
[R]CC(C)=O
[R]OCC=C(C)C
[R]COC1OC(CO)C(O)C(O)C1O
[R]C(C)CCC=C(C)C(O)=O
[R]C(C)=CC
[R]OC(=O)c1c(C)cc(O)cc1O
[R]OC(=O)C(C)=CC
[R]C(C)CCC=C(C)C
[R]c1ccc(O)c(OC)c1
[R]CCC=C(C)C
[R]C(C)CO
[R]OCC
[R]N(C)C
[R]C(CCC(=C)C(C)C)C(O)=O
[R]C=CC(C)=CC(C)CC
[R]C(C)CC(=O)CC(C)C(O)=O
[R]CC(=O)OC
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]CCCCCCC
[R]C(C)CCC(=C)C(C)C
[R]CCC(=O)OC
[R]COC1OC(C)C(O)C(O)C1O
[R]c1c[nH]c2ccccc12
[R]CCC=C(C)CCC=C(C)C
[R]OC(=O)C(C)CC
[R]C(C)(O)CO
[R]C(N)=O
[R]C=CC=CC(O)=O
[R]c2ccc1OCOc1c2
[R]C=CC(O)=O
[R]C(=C)CO
[R]c1ccoc1
[R]OC1CC(OC)C(O)C(C)O1
[R]COC1OCC(O)C(O)C1O
[R]NC(C)=O
[R]NC
[R]OS(O)(=O)=O
[R]C(=O)OCC
[R]C=CC=CC
[R]C(C)C(CC=C(C)C(O)=O)OC(C)=O
[R]CC=C(C)CCC=C(C)C
[R]C1OC(CO)C(O)C(O)C1O
[R]C(CCC=C(C)C)C(O)=O
[R]C=CC(C)CC
[R]Oc1cc(C)cc(O)c1
[R]CC=C(C)CCC=C(C)CCC=C(C)C
[R]Cc1ccc(OC)cc1
[R]C(C)N(C)C
[R]OC(=O)C=Cc1ccccc1
[R]C(C)CCC(=C)C(C)C(O)=O
[R]C(=O)c1ccccc1
[R]C=CCO
[R]C#CC(C)=C
[R]CCCC
[R]CC=C
********** bacteria
[R]O
[R]C
[R]OC
[R]CO
[R]C(O)=O
[R]C(C)C
[R]CC
[R]N
[R]CC(C)C
[R]C(C)CC
[R]Cl
[R]Cc1ccccc1
[R]C(C)O
[R]OC(C)=O
[R]N(C)C
[R]OC1OC(CO)C(O)C(O)C1O
[R]Cc1ccc(O)cc1
[R]C(=O)OC
[R]CCCN=C(N)N
[R]CC(O)=O
[R]CC(N)=O
[R]C(C)=O
[R]CCC(N)=O
[R]CCC
[R]NC(C)=O
[R]C=O
[R]OC1CC(O)C(O)C(C)O1
[R]c1ccc(O)cc1
[R]n1ccc(=O)[nH]c1=O
[R]C(N)=O
[R]OC(N)=O
[R]Cc1c[nH]c2ccccc12
[R]CCC(O)=O
[R]OC1OC(C)C(O)C(O)C1O
[R]N(=O)=O
[R]COC(C)=O
[R]C=C
[R]NC
[R]Br
[R]CC=C(C)C
[R]c1ccccc1
[R]OC1CCC(O)C(C)O1
[R]C(C)=C
[R]COC
[R]OC1CC(OC)C(O)C(C)O1
[R]C(C)(C)O
[R]CN
[R]CCCCN
[R]CCc1ccc(O)cc1
[R]n1cnc2c(N)ncnc12
[R]CCCCC
[R]OS(O)(=O)=O
[R]CCO
[R]CC=O
[R]NC=O
[R]CCCC
[R]OC(=O)C(C)C
[R]c1ccc(O)c(O)c1
[R]CCCN
[R]NC(=O)OC
[R]c1ccccc1O
[R]OC(=O)CC(O)=O
[R]SC
[R]Cc1ccc(OC)cc1
[R]OC1OCC(O)C(O)C1O
[R]OC1OC(C)CC(N(C)C)C1O
[R]C(C)C(O)=O
[R]COC1OC(CO)C(O)C(O)C1O
[R]OC(=O)C(C)=CC
[R]C=CC
[R]CCc1ccccc1
[R]CCN
[R]CCCCCC
[R]CC(C)=O
[R]OC1OC(C)C(O)C(N)C1O
[R]C(O)C(O)=O
[R]CC(C)O
[R]CCCCCCC
[R]C(O)C(N)=O
[R]COC1OC(C)C(O)C(OC)C1OC
[R]OC1OC(CO)C(O)C(O)C1NC(C)=O
[R]OP(O)(O)=O
[R]C1=CC(=O)OC1
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]CC(=O)OC
[R]OC1CC(C)(O)C(O)C(C)O1
[R]OC1CC(O)C(OC)C(C)O1
[R]c1ccc(=O)oc1
[R]C=CC=CC
[R]C(C)=CC
[R]C#N
[R]C1OC(CO)C(O)C1O
[R]c1c[nH]c2ccccc12
[R]CCSC
[R]C(C)(C)C=C
[R]OC(=O)CC(C)C
[R]c1ccc(OC)cc1
[R]COC(N)=O
[R]C(O)C(C)C
[R]OC(=O)CC
********** animals
[R]O
[R]C
[R]OC
[R]CO
[R]OC(C)=O
[R]OC1OC(CO)C(O)C(O)C1O
[R]C(O)=O
[R]Br
[R]OS(O)(=O)=O
[R]C(C)C
[R]OC1OC(C)C(O)C(O)C1O
[R]C(=O)OC
[R]N
[R]Cl
[R]CC
[R]CC=C(C)C
[R]C=O
[R]c1ccc(O)cc1
[R]COC(C)=O
[R]OC1OCC(O)C(O)C1O
[R]C(C)CC
[R]C(C)=C
[R]Cc1ccccc1
[R]C(C)=O
[R]OC1OC(CO)C(O)C(OC)C1O
[R]c1ccc(O)c(O)c1
[R]CC(C)C
[R]C=C
[R]OC(=O)c1ccccc1
[R]C(C)O
[R]c1ccccc1
[R]n1cnc2c(N)ncnc12
[R]OP(O)(O)=O
[R]NC(C)=O
[R]c1ccc(O)c(OC)c1
[R]C(C)(C)O
[R]C1=CC(=O)OC1
[R]OC1OCC(O)C(O)C1OC
[R]COS(O)(=O)=O
[R]CCC(O)=O
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]CCC=C(C)C
[R]CC(O)=O
[R]C(C)CCCC(C)C
[R]COC1OC(CO)C(O)C(O)C1O
[R]N(C)C
[R]OC(=O)C(C)=CC
[R]OC1CC(OC)C(O)C(C)O1
[R]C(O)C(O)CO
[R]c1ccc(OC)cc1
[R]Cc1ccc(O)cc1
[R]c1ccoc1
[R]CCCC(C)=C
[R]c1ccc(OC)c(OC)c1
[R]CCC
[R]c1ccc(=O)oc1
[R]OC(=O)CC(C)C
[R]COC
[R]C(C)CCCC(C)CO
[R]SC
[R]C=C(C)C
[R]CCCC(C)C
[R]CCO
[R]CC=C
[R]c1cc(OC)c(O)c(OC)c1
[R]CC=C(C)CCC=C(C)C
[R]C(O)CO
[R]OC1OC(C(O)=O)C(O)C(O)C1O
[R]C(C)C=CC(C)C(C)C
[R]C(C)(O)CC(=O)CC(C)C
[R]C(C)N(C)C
[R]OC1OCC(OC)C(O)C1OC
[R]CC=CC#C
[R]C(C)CCC(CC)C(C)C
[R]CCCO
[R]COC1OCC(O)C(O)C1O
[R]C(C)CCC=C(C)C
[R]Cc1ccc(OC)cc1
[R]OC1OCC(O)C(OC)C1O
[R]COC1OC(C)C(O)C(O)C1O
[R]C(C)CCC(=C)C(C)C
[R]C1OC(CO)C(O)C(O)C1O
[R]COC(=O)c1cc(O)c(O)c(O)c1
[R]c2ccc1OCOc1c2
[R]CCC(C)(O)C=C
[R]C(C)(C)C=C
[R]CC(N)=O
[R]CCCN=C(N)N
[R]C(=O)OC1OC(CO)C(O)C(O)C1O
[R]C(N)=O
[R]c1cc(O)c(O)c(O)c1
[R]COP(O)(O)=O
[R]CC(N)C(O)=O
[R]OC1OC(CO)C(O)C1O
[R]CCN(C)C
[R]c1ccc(OC)c(O)c1
[R]CCN
[R]COC(=O)C=Cc1ccc(O)cc1
[R]OC(=O)CCC
[R]c1ccc(O)cc1O
********** sponge
[R]C
[R]O
[R]OC
[R]Br
[R]CO
[R]OC(C)=O
[R]C(O)=O
[R]C(C)C
[R]CC
[R]N
[R]OC1OC(CO)C(O)C(O)C1O
[R]C(=O)OC
[R]C=O
[R]OS(O)(=O)=O
[R]CC(C)C
[R]Cl
[R]CC(O)=O
[R]C(C)CC
[R]Cc1ccccc1
[R]NC(C)=O
[R]C(C)O
[R]OC1OC(C)C(O)C(O)C1O
[R]C(C)=O
[R]COC(C)=O
[R]c1ccc(O)cc1
[R]CC(N)=O
[R]Cc1ccc(O)cc1
[R]OC1OC(CO)C(O)C(O)C1NC(C)=O
[R]C=C
[R]CC(=O)OC
[R]C(C)=C
[R]CC1(C)C(C)CCC2(C)C1CCCC2=C
[R]C(C)CCCC(C)C
[R]NC=O
[R][N+]#[C-]
[R]OC(=O)c1ccccc1
[R]CCC(N)=O
[R]OC1OCC(O)C(O)C1O
[R]C(C)(C)O
[R]N=C=S
[R]c1ccc(O)c(O)c1
[R]C(C)C(O)=O
[R]C(C)CCC(=C)C(C)C
[R]C(C)C=CC(C)C(C)C
[R]CCCN=C(N)N
[R]OCC
[R]CC1(C)C(C)CCC2(C)C1CCC=C2C
[R]COC
[R]OC1CC(OC)C(O)C(C)O1
[R]c1c[nH]c2cc(Br)ccc12
[R]C(C)CCC(CC)C(C)C
[R]CC=C(C)C
[R]C(C)CCC(C)C(C)C
[R]OC(=O)CCC
[R]OP(O)(O)=O
[R]C(C)C(=O)OC
[R]CNC(=O)c1cc(Br)c(Br)[nH]1
[R]c1c[nH]c(N)n1
[R]Cc1ccc(OC)cc1
[R]C1(C)CCCC(C)(C)C1
[R]C(O)CO
[R]CCC
[R]C(C)CCC=C(C)C
[R]C#N
[R]C(C)C=CCC(C)C
[R]C1=CC(=O)OC1O
[R]C(=O)OCCCCN=C(N)N
[R]COC(=O)C(C)=CC
[R]CNC(=O)c1cc(Br)c[nH]1
[R]c1c[nH]c2ccccc12
[R]CCN
[R]Cc1c[nH]c2ccccc12
[R]NC
[R]I
[R]C(OC)c1ccc(O)cc1
[R]OC(=O)CC(O)CC
[R]c2nccc3c1ccccc1[nH]c23
[R]C(C)CC(=O)C=C(C)C
[R]C(C)C(C)C
[R]C=C(C)C
[R]C1CSC(=O)N1
[R]c1ccccc1
[R]C(N)=O
[R]OC1OC(C(O)CO)C(O)C1O
[R]OC(=O)C(C)=CC
[R]c1ccc(O)c(OC)c1
[R]N(C)C
[R]Nc1nc(=O)n(C)c1=O
[R]CCCC
[R]Cc1c(Br)[nH]c2ccccc12
[R]CCC(O)=O
[R]CCCCCCCCC
[R]CCO
[R]COC1OC(C)C(O)C(O)C1O
[R]Cc1ccoc1
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]OCCCN(C)C
[R]CCC=C(C)C
[R]COC1OC(CO)C(O)C(O)C1O
[R]c1ccc(OC)cc1
********** corals
[R]C
[R]O
[R]OC(C)=O
[R]C(C)C
[R]CO
[R]OC
[R]C(C)=C
[R]C(=O)OC
[R]Cl
[R]OC(=O)CCC
[R]COC(C)=O
[R]C(O)=O
[R]OC1OC(CO)C(O)C(O)C1O
[R]C=C
[R]C(C)CCC(=C)C(C)C
[R]C(C)(C)O
[R]OO
[R]C=O
[R]Br
[R]C(C)C(C)C
[R]C=C(C)C
[R]OC(=O)CC(C)C
[R]OC1OC(C)C(O)C(O)C1O
[R]CC=CCCCCC
[R]C(C)CCC=C(C)C
[R]C(C)=O
[R]C(C)C1CC1(C)C(C)C(C)C
[R]CCO
[R]OC1OCC(O)C(O)C1O
[R]C(C)CCC(C)C(C)C
[R]C(C)CCCC(C)C
[R]C(C)C=CC(C)C(C)C
[R]OC(=O)CC
[R]CCl
[R]c1ccc(O)c(O)c1
[R]OC(=O)CCCCCCC
[R]C(=C)C(=O)OC
[R]OC(=O)C=Cc1cn(C)cn1
[R]CC=C(C)C
[R]COC
[R]CC
[R]OC(=O)c1ccccc1
[R]C(C)C=CCC(C)C
[R]c1ccc(O)cc1
[R]C(C)(C)OC(C)=O
[R]C2=CC(O)C1CC(O)CCC1(C)C2=O
[R]OCC
[R]OC(=O)C=Cc1ccc(O)c(OC)c1
[R]CCOC(C)=O
[R]CCC=C(C)C
[R]OC(=O)C(C)C
[R]CCc1cc(O)ccc1C
[R]C(OC(C)=O)C(OC(C)=O)C=C(C)C
[R]COC(=O)C=Cc1ccc(O)c(OC)c1
[R]C(C)(O)CCCC(C)C
[R]I
[R]CC(C)=O
[R]C(C)C1CC1C(C)C(C)C
[R]C(C)C(=O)OC
[R]N
[R]C2CC=C1CC(O)CCC1(C)C2=O
[R]C(C)C=CC(C)C
[R]OC(=O)CCCCC
[R]c1ccccc1
[R]C(C)C=CC(=C)C(C)C
[R]OC(=O)C(C)CC
[R]C(=C)C(O)=O
[R]C(C)CCC(=C)C(C)C(O)=O
[R]CC=CCCCC(O)=O
[R]OC(=O)C(C)=CC
[R]CCC1OC(CN)CC1O
[R]CN
[R]CC=CCCCC(=O)OC
[R]CCC(C)=O
[R]C(C)CCC(C)C(C)(C)O
[R]CC(O)=O
[R]C1(C)CO1
[R]OC(=O)COC(=O)CC(C)C
[R]CCCCC
[R]C(C)CO
[R]C(C)COC(C)=O
[R]OC1OC(C)C(OC(C)=O)C(O)C1O
[R]c1cc(OC)c(OC)c(OC)c1
[R]C(C)=CC=CC(C)(C)O
[R]CC=CC#C
[R]C(=COC)C(=O)OC
[R]C(=O)OCC
[R]COC(=O)C=Cc1ccc(O)cc1
[R]OC1OCC(OC(C)=O)C(O)C1O
[R]COC(=O)CC(C)C
[R]C1CCC(C)(C=C)C(C(C)=C)C1
[R]C(=O)OC1OC(CO)C(O)C(O)C1O
[R]OC(=O)CO
[R]C=CC=C(C)C
[R]NC(C)=O
[R]C(C)(O)CO
[R]C(COC(C)=O)=CCC(O)C(C)(C)O
[R]CC(=O)OC
[R]OC(=O)c1cc(O)c(O)c(O)c1
[R]N(C)C