data_414 # _chem_comp.id 414 _chem_comp.name "(5R,6R,8S)-8-(3-{[AMINO(IMINO)METHYL]AMINO}PHENYL)-5-CYCLOHEXYL-6-HYDROXY-3-OXO-1-PHENYL-2,7-DIOXA-4-AZA-6-PHOSPHANONAN-9-OIC ACID 6-OXIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H31 N4 O7 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-04-20 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 518.499 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 414 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details "OpenEye OEToolkits" _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code ? _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal 414 C37 C37 C 0 1 Y N N 16.976 29.075 53.734 -7.510 -1.511 -0.717 C37 414 1 414 C38 C38 C 0 1 Y N N 17.773 29.659 52.711 -8.722 -1.896 -0.175 C38 414 2 414 C39 C39 C 0 1 Y N N 17.570 29.294 51.352 -8.776 -2.950 0.718 C39 414 3 414 C40 C40 C 0 1 Y N N 16.572 28.345 51.009 -7.618 -3.620 1.067 C40 414 4 414 C41 C41 C 0 1 Y N N 15.779 27.761 52.026 -6.407 -3.235 0.524 C41 414 5 414 C36 C36 C 0 1 Y N N 15.978 28.125 53.394 -6.353 -2.180 -0.367 C36 414 6 414 C33 C33 C 0 1 N N N 15.182 27.553 54.394 -5.032 -1.760 -0.959 C33 414 7 414 O32 O32 O 0 1 N N N 14.051 26.761 53.985 -4.418 -0.754 -0.110 O32 414 8 414 C30 C30 C 0 1 N N N 13.316 26.149 54.962 -3.224 -0.271 -0.500 C30 414 9 414 O31 O31 O 0 1 N N N 13.584 26.294 56.169 -2.708 -0.677 -1.522 O31 414 10 414 N29 N29 N 0 1 N N N 12.294 25.424 54.509 -2.601 0.665 0.243 N29 414 11 414 C25 C25 C 0 1 N N R 11.364 24.683 55.354 -1.301 1.192 -0.181 C25 414 12 414 C50 C50 C 0 1 N N N 9.925 25.199 55.152 -1.297 2.715 -0.038 C50 414 13 414 C51 C51 C 0 1 N N N 9.529 25.232 53.638 -2.477 3.303 -0.814 C51 414 14 414 C52 C52 C 0 1 N N N 8.143 25.896 53.427 -2.472 4.827 -0.671 C52 414 15 414 C53 C53 C 0 1 N N N 8.113 27.330 54.018 -1.163 5.388 -1.230 C53 414 16 414 C54 C54 C 0 1 N N N 8.432 27.293 55.529 0.017 4.799 -0.454 C54 414 17 414 C55 C55 C 0 1 N N N 9.811 26.640 55.770 0.012 3.276 -0.597 C55 414 18 414 P24 P24 P 0 1 N N R 11.622 22.887 55.074 0.013 0.479 0.862 P24 414 19 414 O34 O34 O 0 1 N N N 10.625 22.120 55.855 -0.075 -1.127 0.814 O34 414 20 414 O35 O35 O 0 1 N N N 13.065 22.729 55.371 -0.160 0.942 2.258 O35 414 21 414 O23 O23 O 0 1 N N N 11.438 22.586 53.497 1.450 0.955 0.314 O23 414 22 414 C1 C1 C 0 1 N N S 12.001 21.335 53.008 2.677 0.649 0.979 C1 414 23 414 C2 C2 C 0 1 N N N 13.480 21.518 52.577 3.374 1.929 1.362 C2 414 24 414 O14 O14 O 0 1 N N N 14.225 20.508 52.661 4.553 1.887 2.002 O14 414 25 414 O13 O13 O 0 1 N N N 13.843 22.664 52.234 2.871 2.994 1.092 O13 414 26 414 C3 C3 C 0 1 Y N N 11.125 20.693 51.891 3.563 -0.149 0.058 C3 414 27 414 C8 C8 C 0 1 Y N N 11.654 19.662 51.071 4.305 -1.202 0.555 C8 414 28 414 C4 C4 C 0 1 Y N N 9.764 21.079 51.721 3.628 0.170 -1.286 C4 414 29 414 C5 C5 C 0 1 Y N N 8.954 20.437 50.744 4.439 -0.560 -2.135 C5 414 30 414 C6 C6 C 0 1 Y N N 9.494 19.408 49.927 5.188 -1.611 -1.643 C6 414 31 414 C7 C7 C 0 1 Y N N 10.847 19.018 50.085 5.121 -1.938 -0.295 C7 414 32 414 N9 N9 N 0 1 N N N 11.358 18.021 49.324 5.874 -3.005 0.206 N9 414 33 414 C10 C10 C 0 1 N N N 12.460 18.164 48.558 7.150 -3.225 -0.260 C10 414 34 414 N12 N12 N 0 1 N N N 13.086 19.346 48.442 7.809 -4.284 0.119 N12 414 35 414 N11 N11 N 0 1 N N N 12.916 17.111 47.891 7.731 -2.328 -1.126 N11 414 36 414 H37 H37 H 0 1 N N N 17.130 29.354 54.766 -7.469 -0.690 -1.418 H37 414 37 414 H38 H38 H 0 1 N N N 18.534 30.381 52.967 -9.627 -1.373 -0.448 H38 414 38 414 H39 H39 H 0 1 N N N 18.177 29.740 50.578 -9.723 -3.251 1.142 H39 414 39 414 H40 H40 H 0 1 N N N 16.418 28.069 49.976 -7.660 -4.443 1.765 H40 414 40 414 H41 H41 H 0 1 N N N 15.020 27.037 51.767 -5.502 -3.758 0.798 H41 414 41 414 H331 1H33 H 0 0 N N N 15.837 26.892 54.981 -4.374 -2.626 -1.030 H331 414 42 414 H332 2H33 H 0 0 N N N 14.746 28.409 54.930 -5.195 -1.345 -1.954 H332 414 43 414 HN29 HN29 H 0 0 N N N 12.155 25.385 53.520 -3.013 0.990 1.060 HN29 414 44 414 H25 H25 H 0 1 N N N 11.556 24.851 56.424 -1.123 0.924 -1.223 H25 414 45 414 H50 H50 H 0 1 N N N 9.232 24.511 55.658 -1.386 2.981 1.015 H50 414 46 414 H511 1H51 H 0 0 N N N 10.286 25.809 53.086 -2.388 3.037 -1.867 H511 414 47 414 H512 2H51 H 0 0 N N N 9.476 24.196 53.271 -3.409 2.904 -0.416 H512 414 48 414 H521 1H52 H 0 0 N N N 7.934 25.951 52.348 -3.313 5.246 -1.224 H521 414 49 414 H522 2H52 H 0 0 N N N 7.383 25.290 53.942 -2.561 5.093 0.382 H522 414 50 414 H531 1H53 H 0 0 N N N 8.864 27.949 53.505 -1.074 5.121 -2.283 H531 414 51 414 H532 2H53 H 0 0 N N N 7.109 27.756 53.874 -1.160 6.473 -1.128 H532 414 52 414 H541 1H54 H 0 0 N N N 8.445 28.321 55.921 0.949 5.199 -0.852 H541 414 53 414 H542 2H54 H 0 0 N N N 7.661 26.701 56.044 -0.072 5.065 0.599 H542 414 54 414 H551 1H55 H 0 0 N N N 9.972 26.564 56.855 0.853 2.856 -0.044 H551 414 55 414 H552 2H55 H 0 0 N N N 10.566 27.271 55.279 0.101 3.010 -1.650 H552 414 56 414 HO34 HO34 H 0 0 N N N 10.964 21.956 56.727 0.030 -1.501 -0.071 HO34 414 57 414 H1 H1 H 0 1 N N N 11.995 20.619 53.843 2.469 0.067 1.877 H1 414 58 414 HO14 HO14 H 0 0 N N N 15.113 20.748 52.423 4.962 2.734 2.227 HO14 414 59 414 H8 H8 H 0 1 N N N 12.683 19.360 51.195 4.251 -1.454 1.604 H8 414 60 414 H4 H4 H 0 1 N N N 9.346 21.862 52.336 3.044 0.992 -1.674 H4 414 61 414 H5 H5 H 0 1 N N N 7.923 20.733 50.623 4.487 -0.308 -3.184 H5 414 62 414 H6 H6 H 0 1 N N N 8.874 18.924 49.187 5.821 -2.181 -2.307 H6 414 63 414 HN9 HN9 H 0 1 N N N 10.896 17.134 49.330 5.496 -3.590 0.881 HN9 414 64 414 HN12 HN12 H 0 0 N N N 12.622 20.038 48.995 7.400 -4.917 0.730 HN12 414 65 414 H111 1H11 H 0 0 N N N 13.732 17.360 47.369 7.314 -1.466 -1.283 H111 414 66 414 H112 2H11 H 0 0 N N N 12.503 16.200 47.908 8.556 -2.558 -1.581 H112 414 67 # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal 414 C37 C38 DOUB Y N 1 414 C37 C36 SING Y N 2 414 C37 H37 SING N N 3 414 C38 C39 SING Y N 4 414 C38 H38 SING N N 5 414 C39 C40 DOUB Y N 6 414 C39 H39 SING N N 7 414 C40 C41 SING Y N 8 414 C40 H40 SING N N 9 414 C41 C36 DOUB Y N 10 414 C41 H41 SING N N 11 414 C36 C33 SING N N 12 414 C33 O32 SING N N 13 414 C33 H331 SING N N 14 414 C33 H332 SING N N 15 414 O32 C30 SING N N 16 414 C30 N29 SING N N 17 414 C30 O31 DOUB N N 18 414 N29 C25 SING N N 19 414 N29 HN29 SING N N 20 414 C25 P24 SING N N 21 414 C25 C50 SING N N 22 414 C25 H25 SING N N 23 414 C50 C51 SING N N 24 414 C50 C55 SING N N 25 414 C50 H50 SING N N 26 414 C51 C52 SING N N 27 414 C51 H511 SING N N 28 414 C51 H512 SING N N 29 414 C52 C53 SING N N 30 414 C52 H521 SING N N 31 414 C52 H522 SING N N 32 414 C53 C54 SING N N 33 414 C53 H531 SING N N 34 414 C53 H532 SING N N 35 414 C54 C55 SING N N 36 414 C54 H541 SING N N 37 414 C54 H542 SING N N 38 414 C55 H551 SING N N 39 414 C55 H552 SING N N 40 414 P24 O23 SING N N 41 414 P24 O35 DOUB N N 42 414 P24 O34 SING N N 43 414 O34 HO34 SING N N 44 414 O23 C1 SING N N 45 414 C1 C3 SING N N 46 414 C1 C2 SING N N 47 414 C1 H1 SING N N 48 414 C2 O13 DOUB N N 49 414 C2 O14 SING N N 50 414 O14 HO14 SING N N 51 414 C3 C8 DOUB Y N 52 414 C3 C4 SING Y N 53 414 C8 C7 SING Y N 54 414 C8 H8 SING N N 55 414 C4 C5 DOUB Y N 56 414 C4 H4 SING N N 57 414 C5 C6 SING Y N 58 414 C5 H5 SING N N 59 414 C6 C7 DOUB Y N 60 414 C6 H6 SING N N 61 414 C7 N9 SING N N 62 414 N9 C10 SING N N 63 414 N9 HN9 SING N N 64 414 C10 N11 SING N N 65 414 C10 N12 DOUB N N 66 414 N12 HN12 SING N N 67 414 N11 H111 SING N N 68 414 N11 H112 SING N N 69 # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor 414 SMILES ACDLabs 10.04 "O=P(OC(c1cccc(NC(=[N@H])N)c1)C(=O)O)(O)C(NC(=O)OCc2ccccc2)C3CCCCC3" 414 SMILES_CANONICAL CACTVS 3.341 "NC(=N)Nc1cccc(c1)[C@H](O[P@@](O)(=O)[C@@H](NC(=O)OCc2ccccc2)C3CCCCC3)C(O)=O" 414 SMILES CACTVS 3.341 "NC(=N)Nc1cccc(c1)[CH](O[P](O)(=O)[CH](NC(=O)OCc2ccccc2)C3CCCCC3)C(O)=O" 414 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(/N)\Nc1cccc(c1)[C@@H](C(=O)O)O[P@@](=O)([C@H](C2CCCCC2)NC(=O)OCc3ccccc3)O" 414 SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(N)Nc1cccc(c1)C(C(=O)O)OP(=O)(C(C2CCCCC2)NC(=O)OCc3ccccc3)O" 414 InChI InChI 1.03 "InChI=1S/C24H31N4O7P/c25-23(26)27-19-13-7-12-18(14-19)20(22(29)30)35-36(32,33)21(17-10-5-2-6-11-17)28-24(31)34-15-16-8-3-1-4-9-16/h1,3-4,7-9,12-14,17,20-21H,2,5-6,10-11,15H2,(H,28,31)(H,29,30)(H,32,33)(H4,25,26,27)/t20-,21+/m0/s1" 414 InChIKey InChI 1.03 FYIHWPJXYUZMQA-LEWJYISDSA-N # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier 414 "SYSTEMATIC NAME" ACDLabs 10.04 "(5R,6R,8S)-8-(3-carbamimidamidophenyl)-5-cyclohexyl-6-hydroxy-3-oxo-1-phenyl-2,7-dioxa-4-aza-6-phosphanonan-9-oic acid 6-oxide" 414 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-(3-carbamimidamidophenyl)-2-[[(R)-cyclohexyl-phenylmethoxycarbonylamino-methyl]-hydroxy-phosphoryl]oxy-ethanoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 414 "Create component" 2007-04-20 EBI 414 "Modify descriptor" 2011-06-04 RCSB #