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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h25,27-29,32H,26H2/b25-23-
;
414 InChIKey         InChI                1.02b FYIHWPJXYUZMQA-NTFMYDFLDM 
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 
# 
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"    
# 
