target,target_id,target_uniprot,target_species,ligand,ligand_id,ligand_species,ligand_pubchem_cid,smiles,inchi,inchikey,type,action,action_comment,endogenous,primary_target,concentration_range,affinity_parameter,affinity_high,affinity_median,affinity_low,original_affinity_units,original_affinity_low_nm,original_affinity_median_nm,original_affinity_high_nm,original_affinity_relation,assay_description,receptor_site,ligand_context,pubmed_id diphosphomevalonate decarboxylase,642,Q62967,Rat,geranyl diphosphate,3051,,445995,C/C(=C\COP(=O)(OP(=O)(O)O)O)/CCC=C(C)C,"InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+",GVVPGTZRZFNKDS-JXMROGBWSA-N,Inhibitor,Feedback inhibition,,yes,,,pIC50,5.3,,4.19,IC50,65000.0,,5000.0,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,16626865|16524256, diphosphomevalonate decarboxylase,642,Q62967,Rat,2-fluoromevalonate 5-diphosphate,3204,,56947015,OC(=O)C(C(CCOP(=O)(OP(=O)(O)O)O)(O)C)F,"InChI=1S/C6H13FO10P2/c1-6(10,4(7)5(8)9)2-3-16-19(14,15)17-18(11,12)13/h4,10H,2-3H2,1H3,(H,8,9)(H,14,15)(H2,11,12,13)",WPXHWHACORBSDS-UHFFFAOYSA-N,Inhibitor,Irreversible inhibition,,,,,pKi,,5.52,,Ki,,3020.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,16626865, diphosphomevalonate decarboxylase,642,P53602,Human,6-fluoromevalonate 5-diphosphate,3205,,56947062,FCC(OP(=O)(OP(=O)(O)O)O)CC(CC(=O)O)(O)C,"InChI=1S/C7H15FO10P2/c1-7(11,3-6(9)10)2-5(4-8)17-20(15,16)18-19(12,13)14/h5,11H,2-4H2,1H3,(H,9,10)(H,15,16)(H2,12,13,14)",YGLNCOGHKIHKSA-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pKi,,7.21,,Ki,,62.0,,=,"recombinant enzyme expressed in E coli, purified, in vitro spectrophotometric assay",,,18823933, diphosphomevalonate decarboxylase,642,P53602,Human,diphosphoglycolyl proline,3206,,73755030,OC(=O)C1CCCN1C(C(P(=O)(O)O)(P(=O)(O)O)O)O,"InChI=1S/C7H15NO10P2/c9-5(10)4-2-1-3-8(4)6(11)7(12,19(13,14)15)20(16,17)18/h4,6,11-12H,1-3H2,(H,9,10)(H2,13,14,15)(H2,16,17,18)",CDFDGXYBANXCPC-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pKi,,8.64,,Ki,,2.3,,=,"recombinant enzyme expressed in E coli, purified, in vitro spectrophotometric assay",,,18823933, diphosphomevalonate decarboxylase,642,Q62967,Rat,P'-geranyl 2-fluoromevalonate 5-diphosphate,3207,,56947087,C/C(=C\COP(=O)(OP(=O)(OCCC(C(C(=O)O)F)(O)C)O)O)/CCC=C(C)C,"InChI=1S/C16H29FO10P2/c1-12(2)6-5-7-13(3)8-10-25-28(21,22)27-29(23,24)26-11-9-16(4,20)14(17)15(18)19/h6,8,14,20H,5,7,9-11H2,1-4H3,(H,18,19)(H,21,22)(H,23,24)/b13-8+",ACYPMTKDKJZHBJ-MDWZMJQESA-N,Inhibitor,Competitive,,,,,pIC50,,5.34,,IC50,,4600.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,17888661, diphosphomevalonate decarboxylase,642,P53602,Human,P'-geranyl 2-fluoromevalonate 5-diphosphate,3207,,56947087,C/C(=C\COP(=O)(OP(=O)(OCCC(C(C(=O)O)F)(O)C)O)O)/CCC=C(C)C,"InChI=1S/C16H29FO10P2/c1-12(2)6-5-7-13(3)8-10-25-28(21,22)27-29(23,24)26-11-9-16(4,20)14(17)15(18)19/h6,8,14,20H,5,7,9-11H2,1-4H3,(H,18,19)(H,21,22)(H,23,24)/b13-8+",ACYPMTKDKJZHBJ-MDWZMJQESA-N,Inhibitor,Competitive,,,,,pKi,,5.38,,Ki,,4150.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,18823933, diphosphomevalonate decarboxylase,642,Q62967,Rat,"P'-geranyl 3,5,7-trihydroxy-3-methylheptanate 7-diphosphate",3208,,11658073,C/C(=C\COP(=O)(OP(=O)(OCCC(CC(CC(=O)O)(O)C)O)O)O)/CCC=C(C)C,"InChI=1S/C18H34O11P2/c1-14(2)6-5-7-15(3)8-10-27-30(23,24)29-31(25,26)28-11-9-16(19)12-18(4,22)13-17(20)21/h6,8,16,19,22H,5,7,9-13H2,1-4H3,(H,20,21)(H,23,24)(H,25,26)/b15-8+",WJXJJEWDRXZOEO-OVCLIPMQSA-N,Inhibitor,Competitive,,,,,pIC50,,5.59,,IC50,,2600.0,,=,"enzyme expressed in E coli, purified, in vitro assay, spectrophotometric assay",,,16524256, diphosphomevalonate decarboxylase,642,Q62967,Rat,"P'-geranyl 3,5,8-trihydroxy-3-methyloctanate 8-diphosphate",3210,,11498992,OC(CC(CC(=O)O)(O)C)CCCOP(=O)(OP(=O)(OC/C=C(/CCC=C(C)C)\C)O)O,"InChI=1S/C19H36O11P2/c1-15(2)7-5-8-16(3)10-12-29-32(26,27)30-31(24,25)28-11-6-9-17(20)13-19(4,23)14-18(21)22/h7,10,17,20,23H,5-6,8-9,11-14H2,1-4H3,(H,21,22)(H,24,25)(H,26,27)/b16-10+",FPMYZHYONYFBNX-MHWRWJLKSA-N,Inhibitor,Competitive,,,,,pIC50,,5.7,,IC50,,2000.0,,=,"enzyme expressed in E coli, purified, in vitro assay, spectrophotometric assay",,,16524256, diphosphomevalonate decarboxylase,642,Q62967,Rat,compound 19 [PMID: 17888661],3211,,56947005,P=POCCC(C(C)C)(O)C,"InChI=1S/C7H16O2P2/c1-6(2)7(3,8)4-5-9-11-10/h6,8,10H,4-5H2,1-3H3",VODAHBTZSLKFBN-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pIC50,,3.92,,IC50,,120000.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,17888661, diphosphomevalonate decarboxylase,642,Q62967,Rat,compound 18 [PMID: 17888661],3212,,56947006,P=POCCC(CC)(O)C,"InChI=1S/C6H14O2P2/c1-3-6(2,7)4-5-8-10-9/h7,9H,3-5H2,1-2H3",QGZAHEYJZLWZDX-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pIC50,,4.1,,IC50,,80000.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,17888661, diphosphomevalonate decarboxylase,642,Q62967,Rat,"2,2-difluoromevalonate 5-diphosphate",3213,,24779755,OC(=O)C(C(CCOP(=O)(OP(=O)(O)O)O)(O)C)(F)F,"InChI=1S/C6H12F2O10P2/c1-5(11,6(7,8)4(9)10)2-3-17-20(15,16)18-19(12,13)14/h11H,2-3H2,1H3,(H,9,10)(H,15,16)(H2,12,13,14)",TYAGFMDNISQMRJ-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pIC50,,5.12,,IC50,,7500.0,,=,"expression of rat enzyme in E coli, purification, in vitro spectrophotometric assay",,,17888661, diphosphomevalonate decarboxylase,642,Q62967,Rat,"P'-geranyl 3,5,9-trihydroxy-3-methylnonanate 9-diphosphate",5621,,11650985,OC(CC(CC(=O)O)(O)C)CCCCOP(=O)(OP(=O)(OC/C=C(/CCC=C(C)C)\C)O)O,"InChI=1S/C20H38O11P2/c1-16(2)8-7-9-17(3)11-13-30-33(27,28)31-32(25,26)29-12-6-5-10-18(21)14-20(4,24)15-19(22)23/h8,11,18,21,24H,5-7,9-10,12-15H2,1-4H3,(H,22,23)(H,25,26)(H,27,28)/b17-11+",PMUQIJKCGIYWGT-GZTJUZNOSA-N,Inhibitor,Competitive,,,,,pKi,,5.19,,Ki,,6500.0,,=,"enzyme expressed in E coli, purified, in vitro assay, spectrophotometric assay",,,16524256, diphosphomevalonate decarboxylase,642,P53602,Human,"analog 3 [Vlattas et al., 1996]",7994,,44306132,CN(CC(=O)O)CCOP(=O)(OP(=O)(O)O)O,"InChI=1S/C5H13NO9P2/c1-6(4-5(7)8)2-3-14-17(12,13)15-16(9,10)11/h2-4H2,1H3,(H,7,8)(H,12,13)(H2,9,10,11)",YERUUUBBRAPJND-UHFFFAOYSA-N,Inhibitor,Competitive,,,,,pKi,,6.12,,Ki,,750.0,,=,,,,, diphosphomevalonate decarboxylase,642,P53602,Human,6-fluoromevalonate pyrophosphate,7996,,44306087,FC[C@](CC(=O)O)(CCOP(=O)(OP(=O)(O)O)O)O,"InChI=1S/C6H13FO10P2/c7-4-6(10,3-5(8)9)1-2-16-19(14,15)17-18(11,12)13/h10H,1-4H2,(H,8,9)(H,14,15)(H2,11,12,13)/t6-/m1/s1",YIGLDWRZXXHIGZ-ZCFIWIBFSA-N,Inhibitor,Competitive,,,,,pKi,,7.43,,Ki,,37.0,,=,,,,,