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Merge pull request #9 from valence-labs/paper
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maclandrol authored Sep 30, 2023
2 parents 376bda4 + c9322a1 commit ce57c44
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1,553 changes: 1,553 additions & 0 deletions expts/notebook/drug-scaffold-benchmark-design.ipynb
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27 changes: 27 additions & 0 deletions expts/notebook/drugs.csv
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dosed_ingredient,indication_class,molecule_chembl_id,molecule_type,oral,pref_name,therapeutic_flag,usan_stem,usan_stem_definition,usan_year,withdrawn_flag,smiles,inchikey,slices,morphing,motif,scaffold,superstructure
False,Enzyme Inhibitor (angiotensin-converting),CHEMBL431,Small molecule,True,SPIRAPRIL,True,-pril,antihypertensives (ACE inhibitors),1987.0,False,CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2,HRWCVUIFMSZDJS-SZMVWBNQSA-N,"['[7*]c1ccccc1', '[8*]CC[C@H](N[C@@H](C)C([19*])=O)C(=O)OCC', '[17*]N1CC2(C[C@H]1C(=O)O)SCCS2']",[7*]c1ccccc1.[17*]N1CC2(C[C@H]1C(=O)O)SCCS2,[17*]N1CC2(C[C@H]1C(=O)O)SCCS2,[1*][C@H](CCc1ccccc1)N[C@@H]([2*])C(=O)N1CC2(C[C@H]1[3*])SCCS2,O=C(CNCCCc1ccccc1)N1CCC2(C1)SCCS2
True,,CHEMBL175691,Small molecule,True,RILPIVIRINE,True,-vir-,"antivirals: non-nucleoside reverse transcriptase inhibitors, not benzoxazinone derivatives",2009.0,False,Cc1cc(/C=C/C#N)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1,YIBOMRUWOWDFLG-ONEGZZNKSA-N,"['[12*]c1c(C)cc(/C=C/C#N)cc1C', '[11*]Nc1ccnc(N[19*])n1', '[18*]c1ccc(C#N)cc1']",[12*]c1c(C)cc(/C=C/C#N)cc1C.[18*]c1ccc(C#N)cc1,[12*]c1c(C)cc(/C=C/C#N)cc1C,[1*]c1cc([2*])cc([3*])c1Nc1ccnc(Nc2ccc([4*])cc2)n1,c1ccc(Nc2ccnc(Nc3ccccc3)n2)cc1
True,Antihypertensive; Diuretic,CHEMBL61593,Small molecule,True,CYCLOTHIAZIDE,True,-thiazide,diuretics (thiazide derivatives),1963.0,False,NS(=O)(=O)c1cc2c(cc1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O,BOCUKUHCLICSIY-UHFFFAOYSA-N,"['[13*]C1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1', None, '[12*]C1CC2C=CC1C2']",[13*]C1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1.[12*]C1CC2C=CC1C2,[13*]C1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1,[1*]c1cc2c(cc1[2*])NC(C1CC3C=CC1C3)NS2(=O)=O,O=S1(=O)NC(C2CC3C=CC2C3)Nc2ccccc21
False,,CHEMBL1496,Small molecule,True,ROSUVASTATIN,True,-stat-,enzyme inhibitors: antihyperlipidemics (HMG-CoA inhibitors),2000.0,False,CC(C)c1nc(N(C)S(C)(=O)=O)nc(-c2ccc(F)cc2)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O,BPRHUIZQVSMCRT-VEUZHWNKSA-N,"['[14*]c1nc(N(C)S(C)(=O)=O)nc(C(C)C)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O', None, '[13*]c1ccc(F)cc1']",[14*]c1nc(N(C)S(C)(=O)=O)nc(C(C)C)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O.[13*]c1ccc(F)cc1,[14*]c1nc(N(C)S(C)(=O)=O)nc(C(C)C)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O,[1*]c1nc([2*])nc(-c2ccc([3*])cc2)c1[4*],c1ccc(-c2ccncn2)cc1
True,,CHEMBL515408,Small molecule,True,MARIBAVIR,True,-vir,antivirals,1998.0,False,CC(C)Nc1nc2cc(Cl)c(Cl)cc2n1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O,KJFBVJALEQWJBS-XUXIUFHCSA-N,"['[15*]n1c(NC(C)C)nc2cc(Cl)c(Cl)cc21', None, '[14*][C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O']",[15*]n1c(NC(C)C)nc2cc(Cl)c(Cl)cc21.[14*][C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O,[14*][C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O,[1*]c1nc2cc([2*])c([3*])cc2n1[C@H]1O[C@@H]([4*])[C@H]([5*])[C@@H]1[6*],c1ccc2c(c1)ncn2[C@@H]1CCCO1
True,,CHEMBL431770,Small molecule,True,ISTRADEFYLLINE,True,-fylline,theophylline derivatives,2003.0,False,CCn1c(=O)c2c(nc(/C=C/c3ccc(OC)c(OC)c3)n2C)n(CC)c1=O,IQVRBWUUXZMOPW-PKNBQFBNSA-N,"['[9*]c1nc2c(c(=O)n(CC)c(=O)n2CC)n1C', '[8*]/C=C/[11*]', '[10*]c1ccc(OC)c(OC)c1']",[9*]c1nc2c(c(=O)n(CC)c(=O)n2CC)n1C.[10*]c1ccc(OC)c(OC)c1,[9*]c1nc2c(c(=O)n(CC)c(=O)n2CC)n1C,[1*]n1c(=O)c2c(nc(/C=C/c3ccc([2*])c([3*])c3)n2[4*])n([5*])c1=O,O=c1[nH]c(=O)c2[nH]c(/C=C/c3ccccc3)nc2[nH]1
True,Inhibitor (platelet); Vasodilator; Antithrombotic,CHEMBL799,Small molecule,True,CILOSTAZOL,True,,,1997.0,False,O=C1CCc2cc(OCCCCc3nnnn3C3CCCCC3)ccc2N1,RRGUKTPIGVIEKM-UHFFFAOYSA-N,"['[7*]c1ccc2c(c1)CCC(=O)N2', '[6*]OCCCCc1nnnn1[17*]', '[16*]C1CCCCC1']",[7*]c1ccc2c(c1)CCC(=O)N2.[16*]C1CCCCC1,[7*]c1ccc2c(c1)CCC(=O)N2,O=C1CCc2cc(OCCCCc3nnnn3C3CCCCC3)ccc2N1,O=C1CCc2cc(OCCCCc3nnnn3C3CCCCC3)ccc2N1
True,,CHEMBL4297528,Small molecule,True,RISDIPLAM,True,-plam,survival motor neurin SMN1 and SMN2 splicing modulators,2018.0,False,Cc1cn2nc(-c3cc(=O)n4cc(N5CCNC6(CC6)C5)ccc4n3)cc(C)c2n1,ASKZRYGFUPSJPN-UHFFFAOYSA-N,"['[6*]c1cc(C)c2nc(C)cn2n1', '[5*]c1cc(=O)n2cc([13*])ccc2n1', '[12*]N1CCNC2(CC2)C1']",[6*]c1cc(C)c2nc(C)cn2n1.[12*]N1CCNC2(CC2)C1,[6*]c1cc(C)c2nc(C)cn2n1,[1*]c1cn2nc(-c3cc(=O)n4cc(N5CCNC6(CC6)C5)ccc4n3)cc([2*])c2n1,O=c1cc(-c2ccc3nccn3n2)nc2ccc(N3CCNC4(CC4)C3)cn12
True,,CHEMBL1289926,Small molecule,True,AXITINIB,True,-tinib,tyrosine kinase inhibitors,2005.0,False,CNC(=O)c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1,RITAVMQDGBJQJZ-FMIVXFBMSA-N,"['[10*]c1ccccc1C(=O)NC', '[9*]Sc1ccc2c(/C=C/[18*])n[nH]c2c1', '[17*]c1ccccn1']",[10*]c1ccccc1C(=O)NC.[17*]c1ccccn1,[10*]c1ccccc1C(=O)NC,[1*]c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1,C(=C/c1n[nH]c2cc(Sc3ccccc3)ccc12)\c1ccccn1
True,,CHEMBL3701238,Small molecule,True,FUTIBATINIB,True,-tinib,tyrosine kinase inhibitors,2019.0,False,C=CC(=O)N1CC[C@H](n2nc(C#Cc3cc(OC)cc(OC)c3)c3c(N)ncnc32)C1,KEIPNCCJPRMIAX-HNNXBMFYSA-N,"['[8*][C@H]1CCN(C(=O)C=C)C1', '[7*]n1nc(C#C[13*])c2c(N)ncnc21', '[12*]c1cc(OC)cc(OC)c1']",[8*][C@H]1CCN(C(=O)C=C)C1.[12*]c1cc(OC)cc(OC)c1,[8*][C@H]1CCN(C(=O)C=C)C1,[1*]N1CC[C@H](n2nc(C#Cc3cc([2*])cc([3*])c3)c3c([4*])ncnc32)C1,C(#Cc1nn([C@H]2CCNC2)c2ncncc12)c1ccccc1
True,,CHEMBL2105759,Small molecule,True,BARICITINIB,True,-tinib,tyrosine kinase inhibitors: tyrosine kinase inhibitors; janus kinase inhibitors,2011.0,False,CCS(=O)(=O)N1CC(CC#N)(n2cc(-c3ncnc4[nH]ccc34)cn2)C1,XUZMWHLSFXCVMG-UHFFFAOYSA-N,"['[11*]C1(CC#N)CN(S(=O)(=O)CC)C1', '[7*]n1cc([14*])cn1', '[13*]c1ncnc2[nH]ccc12']",[11*]C1(CC#N)CN(S(=O)(=O)CC)C1.[13*]c1ncnc2[nH]ccc12,[11*]C1(CC#N)CN(S(=O)(=O)CC)C1,[1*]N1CC([2*])(n2cc(-c3ncnc4[nH]ccc34)cn2)C1,c1nc(-c2cnn(C3CNC3)c2)c2cc[nH]c2n1
True,,CHEMBL3039502,Small molecule,True,DUVELISIB,True,-lisib,phosphatidylinositol 3-kinase (PI3K) inhibitors,2013.0,False,C[C@H](Nc1ncnc2nc[nH]c12)c1cc2cccc(Cl)c2c(=O)n1-c1ccccc1,SJVQHLPISAIATJ-ZDUSSCGKSA-N,"['[2*]c1ncnc2nc[nH]c12', '[3*]N[C@@H](C)c1cc2cccc(Cl)c2c(=O)n1[24*]', '[23*]c1ccccc1']",[2*]c1ncnc2nc[nH]c12.[23*]c1ccccc1,[2*]c1ncnc2nc[nH]c12,[1*][C@H](Nc1ncnc2nc[nH]c12)c1cc2cccc([2*])c2c(=O)n1-c1ccccc1,O=c1c2ccccc2cc(CNc2ncnc3nc[nH]c23)n1-c1ccccc1
True,Antihypertensive,CHEMBL813,Small molecule,True,EPROSARTAN,True,-sartan,angiotensin II receptor antagonists,1994.0,False,CCCCc1ncc(/C=C(\Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)cc1,OROAFUQRIXKEMV-LDADJPATSA-N,"['[10*]c1cccs1', '[11*]C/C(=C\\c1cnc(CCCC)n1C[21*])C(=O)O', '[20*]c1ccc(C(=O)O)cc1']",[10*]c1cccs1.[20*]c1ccc(C(=O)O)cc1,[20*]c1ccc(C(=O)O)cc1,[1*]c1ncc(/C=C(/[2*])Cc2cccs2)n1Cc1ccc([3*])cc1,C(=C\c1cncn1Cc1ccccc1)\Cc1cccs1
False,Antibacterial (systemic),CHEMBL1435,Small molecule,False,CEFAZOLIN,True,cef-,cephalosporins,1972.0,False,Cc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)Cn4cnnn4)[C@H]3SC2)s1,MLYYVTUWGNIJIB-BXKDBHETSA-N,"['[5*]c1nnc(C)s1', '[4*]SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)C[20*])[C@H]2SC1', '[19*]n1cnnn1']",[5*]c1nnc(C)s1.[19*]n1cnnn1,[5*]c1nnc(C)s1,[1*]c1nnc(SCC2=C([2*])N3C(=O)[C@@H](NC(=O)Cn4cnnn4)[C@H]3SC2)s1,O=C(Cn1cnnn1)N[C@@H]1C(=O)N2C=C(CSc3nncs3)CS[C@H]12
True,,CHEMBL2110588,Small molecule,True,ELIGLUSTAT,True,-stat,enzyme inhibitors: glucosyltransferase inhibitors,2009.0,False,CCCCCCCC(=O)N[C@H](CN1CCCC1)[C@H](O)c1ccc2c(c1)OCCO2,FJZZPCZKBUKGGU-AUSIDOKSSA-N,"['[11*]N1CCCC1', '[12*]C[C@@H](NC(=O)CCCCCCC)[C@@H]([19*])O', '[17*]c1ccc2c(c1)OCCO2']",[11*]N1CCCC1.[17*]c1ccc2c(c1)OCCO2,[17*]c1ccc2c(c1)OCCO2,[1*][C@H](CN1CCCC1)[C@H]([2*])c1ccc2c(c1)OCCO2,c1cc2c(cc1CCCN1CCCC1)OCCO2
True,,CHEMBL4585668,Small molecule,True,BELZUTIFAN,True,-ifan,hypoxia-inducible factor (HIF) inhibitors,2020.0,False,CS(=O)(=O)c1ccc(Oc2cc(F)cc(C#N)c2)c2c1[C@H](O)[C@H](F)[C@@H]2F,LOMMPXLFBTZENJ-ZACQAIPSSA-N,"['[4*]S(C)(=O)=O', '[1*]c1ccc(Oc2cc([15*])cc(F)c2)c2c1[C@H](O)[C@H](F)[C@@H]2F', '[14*]C#N']",[4*]S(C)(=O)=O.[14*]C#N,[4*]S(C)(=O)=O,[1*]c1ccc(Oc2cc([2*])cc([3*])c2)c2c1[C@H]([4*])[C@H]([5*])[C@@H]2[6*],c1ccc(Oc2cccc3c2CCC3)cc1
False,"Radioactive Agent,Thyroid Hormone",CHEMBL1544,Small molecule,True,LIOTHYRONINE,True,,,1963.0,False,N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O,AUYYCJSJGJYCDS-LBPRGKRZSA-N,"['[3*]C[C@H](N)C(=O)O', '[2*]c1cc(I)c(O[9*])c(I)c1', '[8*]c1ccc(O)c(I)c1']",[3*]C[C@H](N)C(=O)O.[8*]c1ccc(O)c(I)c1,[3*]C[C@H](N)C(=O)O,[1*]c1cc([2*])c(Oc2ccc([3*])c([4*])c2)c([5*])c1,c1ccc(Oc2ccccc2)cc1
True,Inhibitor (HMG-CoA reductase); Antihyperlipidemic,CHEMBL503,Small molecule,True,LOVASTATIN,True,-stat-,enzyme inhibitors: antihyperlipidemics (HMG-CoA inhibitors),1987.0,False,CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@H]21,PCZOHLXUXFIOCF-BXMDZJJMSA-N,"['[18*][C@@H]1[C@@H]2C(=C[C@H](C)C[C@@H]2OC(=O)[C@@H](C)CC)C=C[C@@H]1C', '[17*]CC[20*]', '[19*][C@@H]1C[C@@H](O)CC(=O)O1']",[18*][C@@H]1[C@@H]2C(=C[C@H](C)C[C@@H]2OC(=O)[C@@H](C)CC)C=C[C@@H]1C.[19*][C@@H]1C[C@@H](O)CC(=O)O1,[18*][C@@H]1[C@@H]2C(=C[C@H](C)C[C@@H]2OC(=O)[C@@H](C)CC)C=C[C@@H]1C,[1*][C@H]1C[C@@H]([2*])C=C2C=C[C@H]([3*])[C@H](CC[C@@H]3C[C@@H]([4*])CC(=O)O3)[C@H]21,O=C1CCC[C@@H](CC[C@H]2CC=CC3=CCCC[C@@H]32)O1
True,,CHEMBL118,Small molecule,True,CELECOXIB,True,-coxib,cyclooxygenase-2 inhibitors,1998.0,False,Cc1ccc(-c2cc(C(F)(F)F)nn2-c2ccc(S(N)(=O)=O)cc2)cc1,RZEKVGVHFLEQIL-UHFFFAOYSA-N,"['[5*]c1ccc(C)cc1', '[4*]c1cc(C(F)(F)F)nn1[14*]', '[13*]c1ccc(S(N)(=O)=O)cc1']",[5*]c1ccc(C)cc1.[13*]c1ccc(S(N)(=O)=O)cc1,[13*]c1ccc(S(N)(=O)=O)cc1,[1*]c1ccc(-c2cc([2*])nn2-c2ccc([3*])cc2)cc1,c1ccc(-c2ccnn2-c2ccccc2)cc1
True,Antibacterial,CHEMBL1753,Small molecule,True,CLINDAMYCIN,True,-mycin,antibiotics (Streptomyces strain),1968.0,False,CCC[C@@H]1C[C@@H](C(=O)N[C@@H]([C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[C@H](C)Cl)N(C)C1,KDLRVYVGXIQJDK-AWPVFWJPSA-N,"['[6*][C@@H]1C[C@@H](CCC)CN1C', '[5*]C(=O)N[C@@H]([10*])[C@H](C)Cl', '[9*][C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O']",[6*][C@@H]1C[C@@H](CCC)CN1C.[9*][C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O,[9*][C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O,[1*][C@@H]1C[C@@H](C(=O)N[C@H]([2*])[C@H]2O[C@H]([3*])[C@H]([4*])[C@@H]([5*])[C@H]2[6*])N([7*])C1,O=C(NC[C@@H]1CCCCO1)[C@@H]1CCCN1
False,,CHEMBL3301607,Small molecule,False,FILGOTINIB,True,-tinib,tyrosine kinase inhibitors,2014.0,False,O=C(Nc1nc2cccc(-c3ccc(CN4CCS(=O)(=O)CC4)cc3)n2n1)C1CC1,RIJLVEAXPNLDTC-UHFFFAOYSA-N,"['[14*]N1CCS(=O)(=O)CC1', '[15*]Cc1ccc(-c2cccc3nc(NC([27*])=O)nn23)cc1', '[1*]C1CC1']",[14*]N1CCS(=O)(=O)CC1.[1*]C1CC1,[14*]N1CCS(=O)(=O)CC1,O=C(Nc1nc2cccc(-c3ccc(CN4CCS(=O)(=O)CC4)cc3)n2n1)C1CC1,O=C(Nc1nc2cccc(-c3ccc(CN4CCS(=O)(=O)CC4)cc3)n2n1)C1CC1
True,Antifungal,CHEMBL1306,Small molecule,False,TERCONAZOLE,True,-conazole,systemic antifungals (miconazole type),1980.0,False,CC(C)N1CCN(c2ccc(OC[C@H]3CO[C@](Cn4cncn4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1,BLSQLHNBWJLIBQ-OZXSUGGESA-N,"['[7*]N1CCN(C(C)C)CC1', '[6*]c1ccc(OC[C@H]2CO[C@](C[18*])(c3ccc(Cl)cc3Cl)O2)cc1', '[17*]n1cncn1']",[7*]N1CCN(C(C)C)CC1.[17*]n1cncn1,[7*]N1CCN(C(C)C)CC1,[1*]N1CCN(c2ccc(OC[C@H]3CO[C@](Cn4cncn4)(c4ccc([2*])cc4[3*])O3)cc2)CC1,c1ccc([C@@]2(Cn3cncn3)OC[C@H](COc3ccc(N4CCNCC4)cc3)O2)cc1
True,,CHEMBL1201752,Small molecule,False,IXABEPILONE,True,,,2003.0,False,C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1,FABUFPQFXZVHFB-PVYNADRNSA-N,"['[2*]c1csc(C)n1', '[3*]/C=C(/[9*])C', '[1*][C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1']",[2*]c1csc(C)n1.[1*][C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1,[1*][C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1,[1*]/C(=C\c1csc([2*])n1)[C@@H]1C[C@@H]2O[C@]2([3*])CCC[C@H]([4*])[C@H]([5*])[C@@H]([6*])C(=O)C([7*])([8*])[C@@H]([9*])CC(=O)N1,O=C1CCCCCCC2O[C@H]2C[C@@H](C=Cc2cscn2)NC(=O)CCC1
True,,CHEMBL2105720,Small molecule,True,LESINURAD,True,-inurad,urate transporter inhibitors,2010.0,False,O=C(O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12,FGQFOYHRJSUHMR-UHFFFAOYSA-N,"['[11*]n1c(Br)nnc1SCC(=O)O', '[10*]c1ccc([15*])c2ccccc12', '[14*]C1CC1']",[11*]n1c(Br)nnc1SCC(=O)O.[14*]C1CC1,[11*]n1c(Br)nnc1SCC(=O)O,[1*]c1nnc([2*])n1-c1ccc(C2CC2)c2ccccc12,c1ccc2c(-n3cnnc3)ccc(C3CC3)c2c1
True,Anti-Inflammatory,CHEMBL6,Small molecule,True,INDOMETHACIN,True,,,1963.0,False,COc1ccc2c(c1)c(CC(=O)O)c(C)n2C(=O)c1ccc(Cl)cc1,CGIGDMFJXJATDK-UHFFFAOYSA-N,"['[2*]OC', '[1*]c1ccc2c(c1)c(CC(=O)O)c(C)n2C([18*])=O', '[16*]c1ccc(Cl)cc1']",[2*]OC.[16*]c1ccc(Cl)cc1,[16*]c1ccc(Cl)cc1,[1*]c1ccc2c(c1)c([2*])c([3*])n2C(=O)c1ccc([4*])cc1,O=C(c1ccccc1)n1ccc2ccccc21
True,,CHEMBL553,Small molecule,True,ERLOTINIB,True,-tinib,tyrosine kinase inhibitors,2001.0,False,C#Cc1cccc(Nc2ncnc3cc(OCCOC)c(OCCOC)cc23)c1,AAKJLRGGTJKAMG-UHFFFAOYSA-N,"['[2*]C#C', '[1*]c1cccc(Nc2ncnc3cc([15*])c(OCCOC)cc23)c1', '[14*]OCCOC']",[2*]C#C.[14*]OCCOC,[14*]OCCOC,[1*]c1cccc(Nc2ncnc3cc([2*])c([3*])cc23)c1,c1ccc(Nc2ncnc3ccccc23)cc1
193 changes: 104 additions & 89 deletions expts/notebook/generation-benchmarking.ipynb
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