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Repository for Series 4 of the Open Source Malaria Consortium
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Compounds sent for biological testing Nov 2018 #62

Closed mbhebhe closed 5 years ago

mbhebhe commented 6 years ago

Here is list of compounds that we have sent to Dundee.

Series 3:

Series 4:

image image image image image 2018 November Dundee Compounds list.zip

MMV Number SMILES InChI InChI Key
MMV1634420 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC(NCCC4=CC=CC=C4)=CN32 InChI=1S/C20H17F2N5O/c21-20(22)28-16-8-6-15(7-9-16)19-26-25-18-12-24-17(13-27(18)19)23-11-10-14-4-2-1-3-5-14/h1-9,12-13,20,23H,10-11H2 OPITXRFBTTVRFQ-UHFFFAOYSA-N
MMV1634421 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCCC4=CC=C(OC)C(OC)=C4)N32 InChI=1S/C22H21F2N5O3/c1-30-17-8-3-14(11-18(17)31-2)9-10-26-19-12-25-13-20-27-28-21(29(19)20)15-4-6-16(7-5-15)32-22(23)24/h3-8,11-13,22,26H,9-10H2,1-2H3 VDXJYWCEOGLVSA-UHFFFAOYSA-N
MMV1634422 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCC@@HC4=CC=CC=C4)N32 InChI=1S/C20H17F2N5O2/c21-20(22)29-15-8-6-14(7-9-15)19-26-25-18-12-23-11-17(27(18)19)24-10-16(28)13-4-2-1-3-5-13/h1-9,11-12,16,20,24,28H,10H2/t16-/m1/s1 MOIHJTIFLGFROE-MRXNPFEDSA-N
MMV1634423 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCC@HC4=CC=CC=C4)N32 InChI=1S/C20H17F2N5O2/c21-20(22)29-15-8-6-14(7-9-15)19-26-25-18-12-23-11-17(27(18)19)24-10-16(28)13-4-2-1-3-5-13/h1-9,11-12,16,20,24,28H,10H2/t16-/m0/s1 MOIHJTIFLGFROE-INIZCTEOSA-N
MMV1634424 FC(OC1=CC=C(C2=NN=C3C=NC=C(NCC4=CC=CC=C4)N32)C=C1)F InChI=1S/C19H15F2N5O/c20-19(21)27-15-8-6-14(7-9-15)18-25-24-17-12-22-11-16(26(17)18)23-10-13-4-2-1-3-5-13/h1-9,11-12,19,23H,10H2 GWROJQFCRZTYNJ-UHFFFAOYSA-N
MMV1634425 COC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCCC4=CC=CC=C4)N32 InChI=1S/C20H19N5O/c1-26-17-9-7-16(8-10-17)20-24-23-19-14-21-13-18(25(19)20)22-12-11-15-5-3-2-4-6-15/h2-10,13-14,22H,11-12H2,1H3 BQLWJIPILDPOQZ-UHFFFAOYSA-N
MMV1634426 NC(C=C1)=CC=C1C(CO)COC2=CN=CC(N23)=NN=C3C4=CC=C(OC(F)F)C=C4 InChI=1S/C21H19F2N5O3/c22-21(23)31-17-7-3-14(4-8-17)20-27-26-18-9-25-10-19(28(18)20)30-12-15(11-29)13-1-5-16(24)6-2-13/h1-10,15,21,29H,11-12,24H2 DWSRIPSLMMOTPD-UHFFFAOYSA-N
MMV1634427 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(CO)C4=CC=C(NC)C=C4)N32 InChI=1S/C22H21F2N5O3/c1-25-17-6-2-14(3-7-17)16(12-30)13-31-20-11-26-10-19-27-28-21(29(19)20)15-4-8-18(9-5-15)32-22(23)24/h2-11,16,22,25,30H,12-13H2,1H3 YOPBTMOYZOBXTE-UHFFFAOYSA-N
MMV1634428 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CS4)N32 InChI=1S/C18H14F2N4O2S/c19-18(20)26-13-5-3-12(4-6-13)17-23-22-15-10-21-11-16(24(15)17)25-8-7-14-2-1-9-27-14/h1-6,9-11,18H,7-8H2 RMZMYNQAPRIYLW-UHFFFAOYSA-N
MMV1634429 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(C)C4=CC=CC=C4)N32 InChI=1S/C21H18F2N4O2/c1-14(15-5-3-2-4-6-15)13-28-19-12-24-11-18-25-26-20(27(18)19)16-7-9-17(10-8-16)29-21(22)23/h2-12,14,21H,13H2,1H3 YELIMUUXHYJNPF-UHFFFAOYSA-N
MMV1634430 FC(C=C1)=C(F)C=C1CCOC2=CN=CC3=NN=C(OCC4=CN=CC=C4)N32 InChI=1S/C19H15F2N5O2/c20-15-4-3-13(8-16(15)21)5-7-27-18-11-23-10-17-24-25-19(26(17)18)28-12-14-2-1-6-22-9-14/h1-4,6,8-11H,5,7,12H2 KXBYYTPVSDHELS-UHFFFAOYSA-N
MMV1634431 FC1=CC(CCOC2=CN=CC3=NN=C(C4=CC5=C(C=C4)N=CN5)N32)=CC=C1F InChI=1S/C20H14F2N6O/c21-14-3-1-12(7-15(14)22)5-6-29-19-10-23-9-18-26-27-20(28(18)19)13-2-4-16-17(8-13)25-11-24-16/h1-4,7-11H,5-6H2,(H,24,25) OKICKLNNAMYKHW-UHFFFAOYSA-N
MMV1634432 COC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32 InChI=1S/C20H18N4O2/c1-25-17-9-7-16(8-10-17)20-23-22-18-13-21-14-19(24(18)20)26-12-11-15-5-3-2-4-6-15/h2-10,13-14H,11-12H2,1H3 FOEYJDQRLPZFOG-UHFFFAOYSA-N
MMV1634433 O=[N+](C(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)[O-] InChI=1S/C19H15N5O3/c25-24(26)16-8-6-15(7-9-16)19-22-21-17-12-20-13-18(23(17)19)27-11-10-14-4-2-1-3-5-14/h1-9,12-13H,10-11H2 XKYBKXJISXRHEZ-UHFFFAOYSA-N
MMV1634434 COC(C=C1)=CC=C1C2=NN=C3C=NC=C(SCCC4=CC=CC=C4)N32 InChI=1S/C20H18N4OS/c1-25-17-9-7-16(8-10-17)20-23-22-18-13-21-14-19(24(18)20)26-12-11-15-5-3-2-4-6-15/h2-10,13-14H,11-12H2,1H3 XKLPATLXLSUHOI-UHFFFAOYSA-N
MMV1634435 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(CO)(CO)C4=CC=CC=C4)N32 InChI=1S/C22H20F2N4O4/c23-21(24)32-17-8-6-15(7-9-17)20-27-26-18-10-25-11-19(28(18)20)31-14-22(12-29,13-30)16-4-2-1-3-5-16/h1-11,21,29-30H,12-14H2 JCCXTGDCGIGQKA-UHFFFAOYSA-N
MMV1634436 C1(OCCC2=CC=CC=C2)=NC=CN3C1=NN=C3C4=CC=CC=C4 InChI=1S/C19H16N4O/c1-3-7-15(8-4-1)11-14-24-19-18-22-21-17(23(18)13-12-20-19)16-9-5-2-6-10-16/h1-10,12-13H,11,14H2 BKUOBYRSGGKOSW-UHFFFAOYSA-N
MMV1634437 COC(C=C1)=CC=C1C2=NN=C3C(OCCC4=CC=CC=C4)=NC=CN32 InChI=1S/C20H18N4O2/c1-25-17-9-7-16(8-10-17)18-22-23-19-20(21-12-13-24(18)19)26-14-11-15-5-3-2-4-6-15/h2-10,12-13H,11,14H2,1H3 KNDAUWHMGBUKCB-UHFFFAOYSA-N
MMV1634438 O=[N+](C(C=C1)=CC=C1C2=NN=C3C(OCCC4=CC=CC=C4)=NC=CN32)[O-] InChI=1S/C19H15N5O3/c25-24(26)16-8-6-15(7-9-16)17-21-22-18-19(20-11-12-23(17)18)27-13-10-14-4-2-1-3-5-14/h1-9,11-12H,10,13H2 QMCCJGVEGJOFQH-UHFFFAOYSA-N
MMV1634439 COC(C=C1)=CC=C1C2=NN=C3C(SCCC4=CC=CC=C4)=NC=CN32 InChI=1S/C20H18N4OS/c1-25-17-9-7-16(8-10-17)18-22-23-19-20(21-12-13-24(18)19)26-14-11-15-5-3-2-4-6-15/h2-10,12-13H,11,14H2,1H3 GEUZYLOQEWPPTC-UHFFFAOYSA-N
MMV1634440 C1(SCCC2=CC=CC=C2)=NC=CN3C1=NN=C3C4=CC=CC=C4 InChI=1S/C19H16N4S/c1-3-7-15(8-4-1)11-14-24-19-18-22-21-17(23(18)13-12-20-19)16-9-5-2-6-10-16/h1-10,12-13H,11,14H2 PXOUQPVRLQGOLD-UHFFFAOYSA-N
MMV1634441 O=[N+](C(C=C1)=CC=C1C2=NN=C3C(SCCC4=CC=CC=C4)=NC=CN32)[O-] InChI=1S/C19H15N5O2S/c25-24(26)16-8-6-15(7-9-16)17-21-22-18-19(20-11-12-23(17)18)27-13-10-14-4-2-1-3-5-14/h1-9,11-12H,10,13H2 NHMKPHMAQGUBEJ-UHFFFAOYSA-N
MMV1634442 C1(NCCC2=CC=CC=C2)=NC=CN3C1=NN=C3C4=CC=CC=C4 InChI=1S/C19H17N5/c1-3-7-15(8-4-1)11-12-20-17-19-23-22-18(24(19)14-13-21-17)16-9-5-2-6-10-16/h1-10,13-14H,11-12H2,(H,20,21) UVSSRDWLOVROPH-UHFFFAOYSA-N
MMV1634443 COC(C=C1)=CC=C1C2=NN=C3C(NCCC4=CC=CC=C4)=NC=CN32 InChI=1S/C20H19N5O/c1-26-17-9-7-16(8-10-17)19-23-24-20-18(22-13-14-25(19)20)21-12-11-15-5-3-2-4-6-15/h2-10,13-14H,11-12H2,1H3,(H,21,22) ZZFSYDDMUBYAFS-UHFFFAOYSA-N
MMV1634444 O=[N+](C(C=C1)=CC=C1C2=NN=C3C(NCCC4=CC=CC=C4)=NC=CN32)[O-] InChI=1S/C19H16N6O2/c26-25(27)16-8-6-15(7-9-16)18-22-23-19-17(21-12-13-24(18)19)20-11-10-14-4-2-1-3-5-14/h1-9,12-13H,10-11H2,(H,20,21) HFBSNRIFQOQABE-UHFFFAOYSA-N
MMV1581298 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(CO)(O)C4=CC=C(F)C(F)=C4)N32 InChI=1S/C21H16F4N4O4/c22-15-6-3-13(7-16(15)23)21(31,10-30)11-32-18-9-26-8-17-27-28-19(29(17)18)12-1-4-14(5-2-12)33-20(24)25/h1-9,20,30-31H,10-11H2 GXKONCOXFIUYEL-UHFFFAOYSA-N
MMV1581295 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(CO)(O)C4=CC=CC=C4)N32 InChI=1S/C21H18F2N4O4/c22-20(23)31-16-8-6-14(7-9-16)19-26-25-17-10-24-11-18(27(17)19)30-13-21(29,12-28)15-4-2-1-3-5-15/h1-11,20,28-29H,12-13H2 LVBNVRWXODMMAV-UHFFFAOYSA-N
MMV689970 C12=NN=C(C3=CC=CC=C3)N1C(OCCC4=CC=CC=C4)=CN=C2 InChI=1S/C19H16N4O/c1-3-7-15(8-4-1)11-12-24-18-14-20-13-17-21-22-19(23(17)18)16-9-5-2-6-10-16/h1-10,13-14H,11-12H2 YRTHPBSIEMFKFB-UHFFFAOYSA-N
MMV1634445 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCC(COC4=CN=CC5=NN=C(C6=CC=C(OC(F)F)C=C6)N54)(CO)C7=CC=CC=C7)N32 InChI=1S/C34H26F4N8O5/c35-32(36)50-24-10-6-21(7-11-24)30-43-41-26-14-39-16-28(45(26)30)48-19-34(18-47,23-4-2-1-3-5-23)20-49-29-17-40-15-27-42-44-31(46(27)29)22-8-12-25(13-9-22)51-33(37)38/h1-17,32-33,47H,18-20H2 SBKLVTZSIUTYAA-UHFFFAOYSA-N
MMV1634446 NC1=C2C(C(C3=CC=CC(S(=O)(N)=O)=C3)=CN2)=NC=N1 InChI=1S/C12H11N5O2S/c13-12-11-10(16-6-17-12)9(5-15-11)7-2-1-3-8(4-7)20(14,18)19/h1-6,15H,(H2,13,16,17)(H2,14,18,19) AZDIWLYPDODQNA-UHFFFAOYSA-N
MMV1634447 FC(C=C1)=CC=C1CN(CC2)CCN2C3=C4C(C=C(C5=CC=CC(S(N)(=O)=O)=C5)S4)=NC=N3 InChI=1S/C23H22FN5O2S2/c24-18-6-4-16(5-7-18)14-28-8-10-29(11-9-28)23-22-20(26-15-27-23)13-21(32-22)17-2-1-3-19(12-17)33(25,30)31/h1-7,12-13,15H,8-11,14H2,(H2,25,30,31) OWXZZWFFXSEZNL-UHFFFAOYSA-N
MMV1634448 NS(C1=CC=CC(C2=CC3=NC=NC(N(C)C)=C3S2)=C1)(=O)=O InChI=1S/C14H14N4O2S2/c1-18(2)14-13-11(16-8-17-14)7-12(21-13)9-4-3-5-10(6-9)22(15,19)20/h3-8H,1-2H3,(H2,15,19,20) CGTVWFYTOADSRO-UHFFFAOYSA-N
MMV1634449 NC1=C2C(C=C(C3=CC=CC(C(O)=O)=C3)S2)=NC=N1 InChI=1S/C13H9N3O2S/c14-12-11-9(15-6-16-12)5-10(19-11)7-2-1-3-8(4-7)13(17)18/h1-6H,(H,17,18)(H2,14,15,16) JYCLMKQWHKSRJT-UHFFFAOYSA-N
MMV897698 FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32 InChI=1S/C20H16F2N4O2/c21-20(22)28-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)27-11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2 AVBCIJLYABLIRW-UHFFFAOYSA-N
MMV1634450 O=C(CSC1=C2C(C=C(C3=CC=CC(OC)=C3)S2)=NC=N1)O InChI=1S/C15H12N2O3S2/c1-20-10-4-2-3-9(5-10)12-6-11-14(22-12)15(17-8-16-11)21-7-13(18)19/h2-6,8H,7H2,1H3,(H,18,19) DYCCEQUNLMNCFJ-UHFFFAOYSA-N
MMV1634451 CC(C(N=C1)=CC=C1C2=CC3=NC=NC(SCC(O)=O)=C3S2)=O InChI=1S/C15H11N3O3S2/c1-8(19)10-3-2-9(5-16-10)12-4-11-14(23-12)15(18-7-17-11)22-6-13(20)21/h2-5,7H,6H2,1H3,(H,20,21) LGDNGRNEECNYDP-UHFFFAOYSA-N
MMV1634452 O=C(CSC1=C2C(SC(C3=CC=CC(SC)=C3)=C2)=NC=N1)O InChI=1S/C15H12N2O2S3/c1-20-10-4-2-3-9(5-10)12-6-11-14(21-7-13(18)19)16-8-17-15(11)22-12/h2-6,8H,7H2,1H3,(H,18,19) MNWOYBNZZSNGOO-UHFFFAOYSA-N
MMV1634453 O=C(CSC1=C2C(C=C(C3=CC=CC(OC(F)(F)F)=C3)S2)=NC=N1)O InChI=1S/C15H9F3N2O3S2/c16-15(17,18)23-9-3-1-2-8(4-9)11-5-10-13(25-11)14(20-7-19-10)24-6-12(21)22/h1-5,7H,6H2,(H,21,22) LVPPRPZWXKYNRR-UHFFFAOYSA-N
MMV1634454 O=C(C)NC1=CC(C2=CC3=NC=NC(SCC(O)=O)=C3S2)=CC=C1 InChI=1S/C16H13N3O3S2/c1-9(20)19-11-4-2-3-10(5-11)13-6-12-15(24-13)16(18-8-17-12)23-7-14(21)22/h2-6,8H,7H2,1H3,(H,19,20)(H,21,22) QITKDVLQZKEZLA-UHFFFAOYSA-N
MMV1634455 O=C(CSC1=C2C(C=C(C3=CC=CS3)S2)=NC=N1)O InChI=1S/C12H8N2O2S3/c15-10(16)5-18-12-11-7(13-6-14-12)4-9(19-11)8-2-1-3-17-8/h1-4,6H,5H2,(H,15,16) AWGWMRKFZPUBMU-UHFFFAOYSA-N
MMV1634456 O=C(CSC1=C2C(C=C(C3=CC=CC(N4CCOCC4)=C3)S2)=NC=N1)O InChI=1S/C18H17N3O3S2/c22-16(23)10-25-18-17-14(19-11-20-18)9-15(26-17)12-2-1-3-13(8-12)21-4-6-24-7-5-21/h1-3,8-9,11H,4-7,10H2,(H,22,23) YNGXIFAWCXNJLT-UHFFFAOYSA-N
MMV1634457 CS(C1=CC(C2=CC3=NC=NC(SCC(O)=O)=C3S2)=CC=C1)(=O)=O InChI=1S/C15H12N2O4S3/c1-24(20,21)10-4-2-3-9(5-10)12-6-11-14(23-12)15(17-8-16-11)22-7-13(18)19/h2-6,8H,7H2,1H3,(H,18,19) BTGDYEPQMXMGFI-UHFFFAOYSA-N
mattodd commented 6 years ago

Great work from everyone @mbhebhe @maratsydney @david1597

@mbhebhe , it looks like there's an issue with a few of those SMILES above. Any obvious reason? Can you please correct? Great to see that these compounds are already in the Master List, including the UNC donated ones.

Let's keep this issue open until we obtain the data. When that happens, post the data to ELN and link to it from here, post a graphical summary on this page below, and then link from here to the wiki, to the page "data not yet included in the wiki" so that we know the data need to be folded in.

Super exciting to have all these compounds sent in. Amongst many other things, it's essential we see how the OHOH compounds do. If potent, they have the potential to become series frontrunners and we'd need to have them examined for solubility and clearance.

mbhebhe commented 5 years ago

@mattodd with those few SMILES, they have these symbols next to each other "[] ()". These symbols are for hyperlinking. So GH read it as a hyperlink. All fixed now. image

If there is an easier way around this please, someone let me know

mattodd commented 5 years ago

OK, nice one @mbhebhe. I wonder if quoting text works better, so that the blue hyperlink doesn't appear? @cdsouthan is there a way of testing whether these SMILES are being picked up correctly despite the inclusion of that hyperlink? Either way, the solution to this little nugget needs to be installed on the TechOps wiki before we close this issue. @mbhebhe can you please be sure to take care of that?

edwintse commented 5 years ago

I've found a fix. You need to add a backslash between [] and (). This removes the hyperlink and gives the correct smiles.

For example, [C@H] (O) (space added between) will be converted to this MMV1634423 | FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCC@HC4=CC=CC=C4)N32 Adding \ between the brackets gives this instead MMV1634423 | FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NC[C@H](O)C4=CC=CC=C4)N32

This should make the correct SMILES searchable but can someone confirm? @mattodd I can add it to the TechOps wiki but I'll need edit access to it.

cdsouthan commented 5 years ago

For searching, you can check that SMILES string renders correctly in the PubChem structure search box https://pubchem.ncbi.nlm.nih.gov/search/search.cgi# . You will find the SMILES option under the "Identity/Similarity" box. Click on "Preview" and you see the image. For newer structures, you may as well do the "Search" at the same time.

My guess is you can do the same in OpenBable, Chemicalize.org, Marvin, ChemDraw, and even good ole' SciFinder

You should be able to do a bulk check via OpenBable or https://pubchem.ncbi.nlm.nih.gov/idexchange/idexchange.cgi but need to watch out you could still get the "wrong" rendering without an error flag

MFernflower commented 5 years ago

@edwintse you can simply insert a ` at the start and end of each smiles string @mattodd

CCCC(=O)C1=C(C(=C(C=C1O)OC)CC2=C(C(C(=C(C2=O)C(=O)CCC)O)(C)C)O)O

edwintse commented 5 years ago

But that doesn't work with a string that contains [] followed by () FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NC[C@H](O)C4=CC=CC=C4)N32

MFernflower commented 5 years ago

@edwintse the symbol used is the grave not an apostrophe

edwintse commented 5 years ago

Ah, right you are. Either way both work.

mattodd commented 5 years ago

@cdsouthan my concern was with what a search engine actually sees. If it sees the text that we see on the page, then the rendering tricks above will work. If it actually sees the underlying structure of the web page (think the binary representation of the Matrix, vs. the Woman in the Red Dress, if you will) then is there a danger that the string will be perceived with hyperlinks, graves, double brackets? And therefore be perceived wrongly? The answer to this question may be simplest to derive through experimental test. Unless the answer is obvious.

drc007 commented 5 years ago

Why not just enclose the SMILES in a \<pre> tag as shown below? https://www.w3schools.com/tags/tag_pre.asp

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(NC[C@H](O)C4=CC=CC=C4)N32
drc007 commented 5 years ago
screenshot 2018-11-22 at 06 55 26
MFernflower commented 5 years ago

@mattodd @mbhebhe When you get the chance can you push the results to this GHI????

mbhebhe commented 5 years ago

@MFernflower we have the potency results for SGS compounds. I created a new issue for the results #65. I will close this one once we have the potency results for the USyd compounds

MFernflower commented 5 years ago

65 results are in!!