data_3EF
# 
_chem_comp.id                                    3EF 
_chem_comp.name                                  "N-{(2S)-3-[(S)-[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl](hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-tyrosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C38 H38 N3 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-10-08 
_chem_comp.pdbx_modified_date                    2013-12-06 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        711.697 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3EF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        4CA5 
_chem_comp.pdbx_subcomponent_list                "PHQ PPH 1JK TYR" 
_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 
3EF OAB  OAB  O 0 1 N N N 14.530 -5.231  -15.687 4.949  -0.032 -1.655 OAB  PHQ 1  
3EF CAH  CAH  C 0 1 Y N N 13.972 1.538   -14.573 9.860  3.934  1.021  CAH  PHQ 2  
3EF CAK  CAK  C 0 1 Y N N 13.948 0.672   -13.480 8.688  4.506  0.563  CAK  PHQ 3  
3EF CAL  CAL  C 0 1 Y N N 14.262 1.035   -15.835 10.090 2.584  0.832  CAL  PHQ 4  
3EF CAQ  CAQ  C 0 1 Y N N 14.201 -0.694  -13.650 7.743  3.727  -0.078 CAQ  PHQ 5  
3EF CAR  CAR  C 0 1 Y N N 14.524 -0.333  -16.007 9.148  1.806  0.185  CAR  PHQ 6  
3EF CBB  CBB  C 0 1 N N N 14.766 -2.590  -15.090 6.944  1.528  -0.967 CBB  PHQ 7  
3EF OBJ  OBJ  O 0 1 N N N 13.874 -3.098  -16.118 6.022  0.973  0.007  OBJ  PHQ 8  
3EF CBM  CBM  C 0 1 N N N 13.875 -4.428  -16.371 5.036  0.185  -0.463 CBM  PHQ 9  
3EF CBP  CBP  C 0 1 Y N N 14.498 -1.204  -14.915 7.970  2.376  -0.262 CBP  PHQ 10 
3EF OAD  OAD  O 0 1 N N N 13.585 -5.504  -20.328 1.126  -0.008 1.311  O1   PPH 11 
3EF PBY  PBY  P 0 1 N N N 14.067 -6.424  -19.270 1.497  -0.303 -0.091 P1   PPH 12 
3EF OAG  OAG  O 0 1 N N N 15.461 -6.218  -18.809 1.661  1.076  -0.905 O2   PPH 13 
3EF CBX  CBX  C 0 1 N N R 13.001 -6.255  -17.798 3.074  -1.219 -0.123 C1   PPH 14 
3EF NBI  NBI  N 0 1 N N N 13.140 -4.844  -17.408 4.146  -0.362 0.389  N1   PPH 15 
3EF CBE  CBE  C 0 1 N N N 11.502 -6.510  -18.056 2.956  -2.467 0.754  C2   PPH 16 
3EF CBQ  CBQ  C 0 1 Y N N 10.754 -6.327  -16.856 4.214  -3.288 0.630  C3   PPH 17 
3EF CAS  CAS  C 0 1 Y N N 10.519 -7.410  -16.007 5.303  -3.009 1.435  C4   PPH 18 
3EF CAM  CAM  C 0 1 Y N N 9.794  -7.259  -14.818 6.457  -3.762 1.321  C5   PPH 19 
3EF CAI  CAI  C 0 1 Y N N 9.302  -5.997  -14.456 6.521  -4.794 0.403  C6   PPH 20 
3EF CAN  CAN  C 0 1 Y N N 9.548  -4.891  -15.284 5.432  -5.073 -0.401 C7   PPH 21 
3EF CAT  CAT  C 0 1 Y N N 10.260 -5.061  -16.480 4.277  -4.323 -0.284 C8   PPH 22 
3EF OAC  OAC  O 0 1 N N N 11.893 -8.126  -21.585 -2.009 -2.725 -1.314 OAC  1JK 23 
3EF CAJ  CAJ  C 0 1 Y N N 16.437 -13.220 -28.155 -6.140 5.844  1.218  CAJ  1JK 24 
3EF CAO  CAO  C 0 1 Y N N 16.923 -11.906 -28.155 -6.803 5.042  0.307  CAO  1JK 25 
3EF CAP  CAP  C 0 1 Y N N 15.775 -13.713 -27.026 -4.798 5.635  1.482  CAP  1JK 26 
3EF CAU  CAU  C 0 1 Y N N 16.742 -11.091 -27.029 -6.128 4.028  -0.343 CAU  1JK 27 
3EF CAV  CAV  C 0 1 Y N N 15.598 -12.888 -25.905 -4.115 4.621  0.842  CAV  1JK 28 
3EF CBA  CBA  C 0 1 Y N N 15.161 -10.964 -23.726 -2.675 2.379  -0.620 CBA  1JK 29 
3EF CBC  CBC  C 0 1 N N N 14.718 -9.726  -21.510 -1.230 0.566  -1.695 CBC  1JK 30 
3EF CBF  CBF  C 0 1 N N N 13.933 -8.123  -19.802 0.192  -1.314 -0.865 CBF  1JK 31 
3EF NBG  NBG  N 0 1 Y N N 16.646 -9.663  -24.663 -4.534 1.888  -1.659 NBG  1JK 32 
3EF OBK  OBK  O 0 1 Y N N 16.305 -9.077  -23.392 -3.689 1.117  -2.050 OBK  1JK 33 
3EF CBN  CBN  C 0 1 N N N 13.014 -8.025  -22.093 -2.269 -1.580 -1.012 CBN  1JK 34 
3EF CBS  CBS  C 0 1 Y N N 15.387 -9.936  -22.878 -2.504 1.335  -1.463 CBS  1JK 35 
3EF CBT  CBT  C 0 1 Y N N 16.063 -11.568 -25.899 -4.777 3.814  -0.081 CBT  1JK 36 
3EF CBU  CBU  C 0 1 Y N N 15.931 -10.772 -24.808 -4.047 2.725  -0.777 CBU  1JK 37 
3EF CBV  CBV  C 0 1 N N S 14.285 -8.259  -21.281 -1.156 -0.607 -0.715 CBV  1JK 38 
3EF N    N    N 0 1 N N N 13.222 -7.732  -23.380 -3.553 -1.176 -0.942 N    TYR 39 
3EF CA   CA   C 0 1 N N S 12.102 -7.579  -24.300 -4.634 -2.122 -1.230 CA   TYR 40 
3EF C    C    C 0 1 N N N 11.514 -8.980  -24.618 -4.880 -2.165 -2.716 C    TYR 41 
3EF O    O    O 0 1 N N N 10.499 -9.012  -25.334 -4.220 -1.477 -3.458 O    TYR 42 
3EF CB   CB   C 0 1 N N N 12.537 -6.853  -25.585 -5.910 -1.671 -0.515 CB   TYR 43 
3EF CG   CG   C 0 1 Y N N 13.799 -7.077  -26.140 -5.703 -1.745 0.976  CG   TYR 44 
3EF CD1  CD1  C 0 1 Y N N 13.942 -7.962  -27.213 -6.002 -2.910 1.657  CD1  TYR 45 
3EF CD2  CD2  C 0 1 Y N N 14.921 -6.374  -25.666 -5.208 -0.649 1.659  CD2  TYR 46 
3EF CE1  CE1  C 0 1 Y N N 15.203 -8.165  -27.792 -5.812 -2.981 3.024  CE1  TYR 47 
3EF CE2  CE2  C 0 1 Y N N 16.177 -6.578  -26.247 -5.017 -0.715 3.026  CE2  TYR 48 
3EF CZ   CZ   C 0 1 Y N N 16.320 -7.469  -27.311 -5.321 -1.881 3.713  CZ   TYR 49 
3EF OH   OH   O 0 1 N N N 17.549 -7.661  -27.888 -5.134 -1.948 5.057  OH   TYR 50 
3EF OXT  OXT  O 0 1 N N N 12.067 -9.992  -24.100 -5.833 -2.968 -3.215 OXT  TYR 51 
3EF HAH  HAH  H 0 1 N N N 13.767 2.590   -14.439 10.598 4.543  1.523  HAH  PHQ 52 
3EF HAK  HAK  H 0 1 N N N 13.733 1.058   -12.495 8.510  5.562  0.707  HAK  PHQ 53 
3EF HAL  HAL  H 0 1 N N N 14.286 1.699   -16.687 11.006 2.137  1.190  HAL  PHQ 54 
3EF HAQ  HAQ  H 0 1 N N N 14.166 -1.357  -12.798 6.827  4.174  -0.436 HAQ  PHQ 55 
3EF HAR  HAR  H 0 1 N N N 14.748 -0.716  -16.992 9.328  0.752  0.037  HAR  PHQ 56 
3EF HBB  HBB  H 0 1 N N N 14.589 -3.126  -14.146 7.444  0.717  -1.497 HBB  PHQ 57 
3EF HBBA HBBA H 0 0 N N N 15.812 -2.731  -15.401 6.393  2.142  -1.680 HBBA PHQ 58 
3EF HOAG HOAG H 0 0 N N N 15.849 -5.493  -19.286 1.905  0.959  -1.834 H1   PPH 59 
3EF HBX  HBX  H 0 1 N N N 13.389 -6.936  -17.027 3.302  -1.514 -1.147 H2   PPH 60 
3EF HNBI HNBI H 0 0 N N N 12.657 -4.156  -17.949 4.216  -0.188 1.341  H4   PPH 61 
3EF HBE  HBE  H 0 1 N N N 11.140 -5.806  -18.820 2.817  -2.169 1.793  H5   PPH 62 
3EF HBEA HBEA H 0 0 N N N 11.366 -7.541  -18.414 2.102  -3.060 0.428  H6   PPH 63 
3EF HAS  HAS  H 0 1 N N N 10.904 -8.384  -16.272 5.253  -2.203 2.151  H7   PPH 64 
3EF HAM  HAM  H 0 1 N N N 9.614  -8.113  -14.182 7.308  -3.544 1.949  H8   PPH 65 
3EF HAI  HAI  H 0 1 N N N 8.736  -5.877  -13.544 7.423  -5.382 0.315  H9   PPH 66 
3EF HAN  HAN  H 0 1 N N N 9.190  -3.912  -15.001 5.483  -5.879 -1.118 H10  PPH 67 
3EF HAT  HAT  H 0 1 N N N 10.432 -4.210  -17.122 3.424  -4.543 -0.909 H11  PPH 68 
3EF HAJ  HAJ  H 0 1 N N N 16.573 -13.849 -29.022 -6.670 6.639  1.721  HAJ  1JK 69 
3EF HAO  HAO  H 0 1 N N N 17.437 -11.521 -29.023 -7.850 5.209  0.104  HAO  1JK 70 
3EF HAP  HAP  H 0 1 N N N 15.401 -14.726 -27.017 -4.284 6.267  2.192  HAP  1JK 71 
3EF HAU  HAU  H 0 1 N N N 17.130 -10.083 -27.032 -6.647 3.402  -1.054 HAU  1JK 72 
3EF HAV  HAV  H 0 1 N N N 15.095 -13.278 -25.033 -3.068 4.459  1.049  HAV  1JK 73 
3EF HBAA HBAA H 0 0 N N N 14.484 -11.789 -23.562 -1.942 2.841  0.025  HBAA 1JK 74 
3EF HBC  HBC  H 0 1 N N N 13.828 -10.370 -21.450 -1.215 0.187  -2.717 HBC  1JK 75 
3EF HBCA HBCA H 0 0 N N N 15.430 -10.011 -20.722 -0.375 1.224  -1.538 HBCA 1JK 76 
3EF HBF  HBF  H 0 1 N N N 12.901 -8.470  -19.644 0.416  -1.448 -1.923 HBF  1JK 77 
3EF HBFA HBFA H 0 0 N N N 14.623 -8.742  -19.209 0.149  -2.287 -0.377 HBFA 1JK 78 
3EF HBV  HBV  H 0 1 N N N 15.083 -7.559  -21.571 -1.260 -0.236 0.305  HBV  1JK 79 
3EF HN   HN   H 0 1 N N N 14.157 -7.616  -23.716 -3.761 -0.260 -0.700 H2   TYR 80 
3EF HA   HA   H 0 1 N N N 11.315 -6.981  -23.817 -4.352 -3.114 -0.879 HA   TYR 81 
3EF HB   HB   H 0 1 N N N 11.802 -7.118  -26.359 -6.142 -0.645 -0.799 HB2  TYR 82 
3EF HBA  HBA  H 0 1 N N N 12.474 -5.775  -25.373 -6.735 -2.323 -0.800 HB3  TYR 83 
3EF HD1  HD1  H 0 1 N N N 13.081 -8.489  -27.596 -6.384 -3.766 1.121  HD1  TYR 84 
3EF HD2  HD2  H 0 1 N N N 14.813 -5.674  -24.851 -4.971 0.258  1.124  HD2  TYR 85 
3EF HE1  HE1  H 0 1 N N N 15.314 -8.860  -28.611 -6.050 -3.890 3.556  HE1  TYR 86 
3EF HE2  HE2  H 0 1 N N N 17.038 -6.045  -25.871 -4.631 0.141  3.559  HE2  TYR 87 
3EF HOH  HOH  H 0 1 N N N 18.194 -7.119  -27.449 -4.255 -2.254 5.317  HH   TYR 88 
3EF HOXT HOXT H 0 0 N N N 11.587 -10.775 -24.343 -5.954 -2.962 -4.175 HXT  TYR 89 
# 
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 
3EF O   C    DOUB N N 1  
3EF C   CA   SING N N 2  
3EF C   OXT  SING N N 3  
3EF CA  N    SING N N 4  
3EF N   CBN  SING N N 5  
3EF N   HN   SING N N 6  
3EF CB  CA   SING N N 7  
3EF CA  HA   SING N N 8  
3EF CG  CB   SING N N 9  
3EF CB  HB   SING N N 10 
3EF CB  HBA  SING N N 11 
3EF CD1 CG   DOUB Y N 12 
3EF CG  CD2  SING Y N 13 
3EF OH  CZ   SING N N 14 
3EF OH  HOH  SING N N 15 
3EF CE1 CZ   DOUB Y N 16 
3EF CZ  CE2  SING Y N 17 
3EF CBM OAB  DOUB N N 18 
3EF CBN OAC  DOUB N N 19 
3EF OAD PBY  DOUB N N 20 
3EF PBY OAG  SING N N 21 
3EF OAG HOAG SING N N 22 
3EF CAL CAH  DOUB Y N 23 
3EF CAH CAK  SING Y N 24 
3EF CAH HAH  SING N N 25 
3EF CAN CAI  DOUB Y N 26 
3EF CAM CAI  SING Y N 27 
3EF CAI HAI  SING N N 28 
3EF CAO CAJ  DOUB Y N 29 
3EF CAJ CAP  SING Y N 30 
3EF CAJ HAJ  SING N N 31 
3EF CAQ CAK  DOUB Y N 32 
3EF CAK HAK  SING N N 33 
3EF CAR CAL  SING Y N 34 
3EF CAL HAL  SING N N 35 
3EF CAS CAM  DOUB Y N 36 
3EF CAM HAM  SING N N 37 
3EF CAT CAN  SING Y N 38 
3EF CAN HAN  SING N N 39 
3EF CAO CAU  SING Y N 40 
3EF CAO HAO  SING N N 41 
3EF CAP CAV  DOUB Y N 42 
3EF CAP HAP  SING N N 43 
3EF CBP CAQ  SING Y N 44 
3EF CAQ HAQ  SING N N 45 
3EF CAR CBP  DOUB Y N 46 
3EF CAR HAR  SING N N 47 
3EF CBQ CAS  SING Y N 48 
3EF CAS HAS  SING N N 49 
3EF CBQ CAT  DOUB Y N 50 
3EF CAT HAT  SING N N 51 
3EF CAU CBT  DOUB Y N 52 
3EF CAU HAU  SING N N 53 
3EF CAV CBT  SING Y N 54 
3EF CAV HAV  SING N N 55 
3EF CBU CBA  SING Y N 56 
3EF CBA CBS  DOUB Y N 57 
3EF CBA HBAA SING N N 58 
3EF OBJ CBB  SING N N 59 
3EF CBB CBP  SING N N 60 
3EF CBB HBB  SING N N 61 
3EF CBB HBBA SING N N 62 
3EF CBS CBC  SING N N 63 
3EF CBC CBV  SING N N 64 
3EF CBC HBC  SING N N 65 
3EF CBC HBCA SING N N 66 
3EF CBE CBX  SING N N 67 
3EF CBE CBQ  SING N N 68 
3EF CBE HBE  SING N N 69 
3EF CBE HBEA SING N N 70 
3EF CBV CBF  SING N N 71 
3EF CBF PBY  SING N N 72 
3EF CBF HBF  SING N N 73 
3EF CBF HBFA SING N N 74 
3EF CBU NBG  DOUB Y N 75 
3EF NBG OBK  SING Y N 76 
3EF CBX NBI  SING N N 77 
3EF NBI CBM  SING N N 78 
3EF NBI HNBI SING N N 79 
3EF CBM OBJ  SING N N 80 
3EF OBK CBS  SING Y N 81 
3EF CBN CBV  SING N N 82 
3EF CBT CBU  SING N N 83 
3EF CBV HBV  SING N N 84 
3EF PBY CBX  SING N N 85 
3EF CBX HBX  SING N N 86 
3EF CE1 CD1  SING Y N 87 
3EF CD1 HD1  SING N N 88 
3EF CE2 CD2  DOUB Y N 89 
3EF CD2 HD2  SING N N 90 
3EF CE1 HE1  SING N N 91 
3EF CE2 HE2  SING N N 92 
3EF OXT HOXT SING N N 93 
# 
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 
3EF SMILES           ACDLabs              12.01 "O=C(O)C(NC(=O)C(CP(=O)(O)C(NC(=O)OCc1ccccc1)Cc2ccccc2)Cc4onc(c3ccccc3)c4)Cc5ccc(O)cc5" 
3EF InChI            InChI                1.03  
;InChI=1S/C38H38N3O9P/c42-31-18-16-27(17-19-31)20-34(37(44)45)39-36(43)30(22-32-23-33(41-50-32)29-14-8-3-9-15-29)25-51(47,48)35(21-26-10-4-1-5-11-26)40-38(46)49-24-28-12-6-2-7-13-28/h1-19,23,30,34-35,42H,20-22,24-25H2,(H,39,43)(H,40,46)(H,44,45)(H,47,48)/t30-,34+,35-/m1/s1
;
3EF InChIKey         InChI                1.03  ZPFSKFCSVXPMBD-JHOVWCEZSA-N 
3EF SMILES_CANONICAL CACTVS               3.385 "OC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](Cc2onc(c2)c3ccccc3)C[P](O)(=O)[C@H](Cc4ccccc4)NC(=O)OCc5ccccc5" 
3EF SMILES           CACTVS               3.385 "OC(=O)[CH](Cc1ccc(O)cc1)NC(=O)[CH](Cc2onc(c2)c3ccccc3)C[P](O)(=O)[CH](Cc4ccccc4)NC(=O)OCc5ccccc5" 
3EF SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)C[C@H](NC(=O)OCc2ccccc2)P(=O)(C[C@@H](Cc3cc(no3)c4ccccc4)C(=O)N[C@@H](Cc5ccc(cc5)O)C(=O)O)O" 
3EF SMILES           "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)CC(NC(=O)OCc2ccccc2)P(=O)(CC(Cc3cc(no3)c4ccccc4)C(=O)NC(Cc5ccc(cc5)O)C(=O)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 
3EF "SYSTEMATIC NAME" ACDLabs              12.01 "N-{(2S)-3-[(S)-[(1R)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl](hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-tyrosine"                                
3EF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-2-[[oxidanyl-[(1R)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoyl]amino]propanoic 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 
3EF "Create component" 2013-10-08 EBI  
3EF "Initial release"  2013-12-11 RCSB 
# 
