data_578
# 
_chem_comp.id                                    578 
_chem_comp.name                                  "(5R,6S,8S)-8-[3-(AMINOMETHYL)PHENYL]-6-HYDROXY-5-ISOPROPYL-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                               "C21 H27 N2 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                        450.422 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     578 
_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                  PDBJ 
# 
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 
578 C27  C27  C 0 1 Y N N 37.130 13.994 68.227 7.171  0.407  -0.742 C27  578 1  
578 C28  C28  C 0 1 Y N N 38.241 13.779 69.082 8.431  0.479  -0.179 C28  578 2  
578 C29  C29  C 0 1 Y N N 39.527 13.542 68.533 8.651  1.285  0.922  C29  578 3  
578 C30  C30  C 0 1 Y N N 39.705 13.518 67.127 7.611  2.020  1.460  C30  578 4  
578 C31  C31  C 0 1 Y N N 38.597 13.730 66.272 6.351  1.948  0.897  C31  578 5  
578 C26  C26  C 0 1 Y N N 37.305 13.972 66.821 6.130  1.141  -0.204 C26  578 6  
578 C23  C23  C 0 1 N N N 36.219 14.206 65.973 4.756  1.063  -0.818 C23  578 7  
578 O22  O22  O 0 1 N N N 36.492 14.489 64.584 4.005  -0.008 -0.189 O22  578 8  
578 C20  C20  C 0 1 N N N 35.428 14.461 63.732 2.748  -0.212 -0.626 C20  578 9  
578 O21  O21  O 0 1 N N N 34.260 14.361 64.155 2.291  0.486  -1.510 O21  578 10 
578 N19  N19  N 0 1 N N N 35.733 14.632 62.446 1.996  -1.191 -0.084 N19  578 11 
578 C15  C15  C 0 1 N N R 34.738 14.598 61.371 0.629  -1.413 -0.559 C15  578 12 
578 C16  C16  C 0 1 N N N 34.813 15.850 60.473 0.395  -2.912 -0.759 C16  578 13 
578 C18  C18  C 0 1 N N N 34.329 17.091 61.234 -0.973 -3.133 -1.406 C18  578 14 
578 C17  C17  C 0 1 N N N 36.203 16.085 59.908 1.487  -3.482 -1.666 C17  578 15 
578 P14  P14  P 0 1 N N S 34.933 13.008 60.473 -0.554 -0.771 0.670  P14  578 16 
578 O24  O24  O 0 1 N N N 34.074 12.998 59.274 -0.345 0.683  0.845  O24  578 17 
578 O25  O25  O 0 1 N N N 34.723 11.980 61.520 -0.324 -1.519 2.077  O25  578 18 
578 O13  O13  O 0 1 N N N 36.485 12.893 60.006 -2.057 -1.040 0.160  O13  578 19 
578 C1   C1   C 0 1 N N S 36.968 11.579 59.621 -3.212 -0.561 0.853  C1   578 20 
578 C2   C2   C 0 1 N N N 37.280 10.709 60.849 -4.073 -1.729 1.261  C2   578 21 
578 O12  O12  O 0 1 N N N 37.043 9.490  60.743 -3.733 -2.855 0.986  O12  578 22 
578 O11  O11  O 0 1 N N N 37.754 11.284 61.852 -5.218 -1.517 1.929  O11  578 23 
578 C3   C3   C 0 1 Y N N 38.231 11.647 58.762 -3.999 0.351  -0.052 C3   578 24 
578 C8   C8   C 0 1 Y N N 38.374 10.741 57.684 -4.572 1.502  0.456  C8   578 25 
578 C4   C4   C 0 1 Y N N 39.308 12.492 59.128 -4.142 0.041  -1.392 C4   578 26 
578 C5   C5   C 0 1 Y N N 40.532 12.417 58.425 -4.864 0.878  -2.222 C5   578 27 
578 C6   C6   C 0 1 Y N N 40.681 11.506 57.351 -5.442 2.025  -1.712 C6   578 28 
578 C7   C7   C 0 1 Y N N 39.598 10.669 56.980 -5.294 2.339  -0.375 C7   578 29 
578 C9   C9   C 0 1 N N N 39.754 9.683  55.828 -5.919 3.593  0.179  C9   578 30 
578 N10  N10  N 0 1 N N N 40.387 8.449  56.317 -4.968 4.706  0.066  N10  578 31 
578 H27  H27  H 0 1 N N N 36.152 14.174 68.647 7.000  -0.219 -1.606 H27  578 32 
578 H28  H28  H 0 1 N N N 38.107 13.796 70.154 9.244  -0.094 -0.600 H28  578 33 
578 H29  H29  H 0 1 N N N 40.371 13.380 69.187 9.636  1.341  1.362  H29  578 34 
578 H30  H30  H 0 1 N N N 40.684 13.338 66.709 7.782  2.648  2.321  H30  578 35 
578 H31  H31  H 0 1 N N N 38.732 13.708 65.201 5.538  2.522  1.317  H31  578 36 
578 H231 1H23 H 0 0 N N N 35.599 13.298 65.995 4.236  2.009  -0.667 H231 578 37 
578 H232 2H23 H 0 0 N N N 35.755 15.125 66.360 4.846  0.865  -1.886 H232 578 38 
578 HN19 HN19 H 0 0 N N N 36.690 14.792 62.202 2.361  -1.748 0.622  HN19 578 39 
578 H15  H15  H 0 1 N N N 33.719 14.636 61.783 0.485  -0.893 -1.507 H15  578 40 
578 H16  H16  H 0 1 N N N 34.146 15.666 59.618 0.426  -3.416 0.207  H16  578 41 
578 H181 1H18 H 0 0 N N N 34.213 16.846 62.300 -1.056 -2.516 -2.301 H181 578 42 
578 H182 2H18 H 0 0 N N N 35.066 17.900 61.122 -1.081 -4.183 -1.678 H182 578 43 
578 H183 3H18 H 0 0 N N N 33.361 17.417 60.826 -1.758 -2.857 -0.701 H183 578 44 
578 H171 1H17 H 0 0 N N N 36.149 16.142 58.811 2.452  -3.405 -1.166 H171 578 45 
578 H172 2H17 H 0 0 N N N 36.605 17.029 60.304 1.271  -4.528 -1.881 H172 578 46 
578 H173 3H17 H 0 0 N N N 36.862 15.254 60.200 1.516  -2.918 -2.599 H173 578 47 
578 HO25 HO25 H 0 0 N N N 34.678 11.121 61.117 -0.371 -2.484 2.023  HO25 578 48 
578 H1   H1   H 0 1 N N N 36.153 11.130 59.033 -2.900 -0.012 1.741  H1   578 49 
578 HO11 HO11 H 0 0 N N N 37.912 10.646 62.538 -5.736 -2.297 2.169  HO11 578 50 
578 H8   H8   H 0 1 N N N 37.549 10.105 57.399 -4.456 1.747  1.501  H8   578 51 
578 H4   H4   H 0 1 N N N 39.194 13.192 59.942 -3.690 -0.856 -1.789 H4   578 52 
578 H5   H5   H 0 1 N N N 41.356 13.056 58.708 -4.975 0.635  -3.268 H5   578 53 
578 H6   H6   H 0 1 N N N 41.617 11.449 56.816 -6.006 2.680  -2.361 H6   578 54 
578 H91  1H9  H 0 1 N N N 38.763 9.446  55.412 -6.822 3.829  -0.384 H91  578 55 
578 H92  2H9  H 0 1 N N N 40.384 10.132 55.046 -6.176 3.439  1.227  H92  578 56 
578 H101 1H10 H 0 0 N N N 40.531 7.822  55.552 -5.364 5.560  0.431  H101 578 57 
578 H102 2H10 H 0 0 N N N 41.267 8.670  56.737 -4.097 4.486  0.527  H102 578 58 
# 
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 
578 C27 C26  SING Y N 1  
578 C27 C28  DOUB Y N 2  
578 C27 H27  SING N N 3  
578 C28 C29  SING Y N 4  
578 C28 H28  SING N N 5  
578 C29 C30  DOUB Y N 6  
578 C29 H29  SING N N 7  
578 C30 C31  SING Y N 8  
578 C30 H30  SING N N 9  
578 C31 C26  DOUB Y N 10 
578 C31 H31  SING N N 11 
578 C26 C23  SING N N 12 
578 C23 O22  SING N N 13 
578 C23 H231 SING N N 14 
578 C23 H232 SING N N 15 
578 O22 C20  SING N N 16 
578 C20 N19  SING N N 17 
578 C20 O21  DOUB N N 18 
578 N19 C15  SING N N 19 
578 N19 HN19 SING N N 20 
578 C15 C16  SING N N 21 
578 C15 P14  SING N N 22 
578 C15 H15  SING N N 23 
578 C16 C17  SING N N 24 
578 C16 C18  SING N N 25 
578 C16 H16  SING N N 26 
578 C18 H181 SING N N 27 
578 C18 H182 SING N N 28 
578 C18 H183 SING N N 29 
578 C17 H171 SING N N 30 
578 C17 H172 SING N N 31 
578 C17 H173 SING N N 32 
578 P14 O24  DOUB N N 33 
578 P14 O13  SING N N 34 
578 P14 O25  SING N N 35 
578 O25 HO25 SING N N 36 
578 O13 C1   SING N N 37 
578 C1  C3   SING N N 38 
578 C1  C2   SING N N 39 
578 C1  H1   SING N N 40 
578 C2  O12  DOUB N N 41 
578 C2  O11  SING N N 42 
578 O11 HO11 SING N N 43 
578 C3  C8   DOUB Y N 44 
578 C3  C4   SING Y N 45 
578 C8  C7   SING Y N 46 
578 C8  H8   SING N N 47 
578 C4  C5   DOUB Y N 48 
578 C4  H4   SING N N 49 
578 C5  C6   SING Y N 50 
578 C5  H5   SING N N 51 
578 C6  C7   DOUB Y N 52 
578 C6  H6   SING N N 53 
578 C7  C9   SING N N 54 
578 C9  N10  SING N N 55 
578 C9  H91  SING N N 56 
578 C9  H92  SING N N 57 
578 N10 H101 SING N N 58 
578 N10 H102 SING N N 59 
# 
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 
578 SMILES           ACDLabs              10.04 O=P(O)(OC(c1cccc(c1)CN)C(=O)O)C(NC(=O)OCc2ccccc2)C(C)C                                                                                                                                                  
578 InChI            InChI                1.02b InChI=1/C21H27N2O7P/c1-14(2)19(23-21(26)29-13-15-7-4-3-5-8-15)31(27,28)30-18(20(24)25)17-10-6-9-16(11-17)12-22/h3-11,14,18-19H,12-13,22H2,1-2H3,(H,23,26)(H,24,25)(H,27,28)/t18-,19+/m0/s1/f/h23-24,27H 
578 InChIKey         InChI                1.02b RTFGEFWZCFCODU-WQTGMYJMDV                                                                                                                                                                               
578 SMILES_CANONICAL CACTVS               3.341 CC(C)[C@H](NC(=O)OCc1ccccc1)[P@@](O)(=O)O[C@H](C(O)=O)c2cccc(CN)c2                                                                                                                                      
578 SMILES           CACTVS               3.341 CC(C)[CH](NC(=O)OCc1ccccc1)[P](O)(=O)O[CH](C(O)=O)c2cccc(CN)c2                                                                                                                                          
578 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)[C@H](NC(=O)OCc1ccccc1)[P@](=O)(O)O[C@@H](c2cccc(c2)CN)C(=O)O                                                                                                                                      
578 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)C(NC(=O)OCc1ccccc1)P(=O)(O)OC(c2cccc(c2)CN)C(=O)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 
578 "SYSTEMATIC NAME" ACDLabs              10.04 "(5R,6S,8S)-8-[3-(aminomethyl)phenyl]-6-hydroxy-5-(1-methylethyl)-3-oxo-1-phenyl-2,7-dioxa-4-aza-6-phosphanonan-9-oic acid 6-oxide" 
578 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[3-(aminomethyl)phenyl]-2-[hydroxy-[(1R)-2-methyl-1-phenylmethoxycarbonylamino-propyl]phosphoryl]oxy-ethanoic acid"         
# 
