data_PRDCC_000334
# 
_chem_comp.id                                    PRD_000334 
_chem_comp.name                                  "BENZYLOXYCARBONYL-GLYCYL-PHENYLALANYL-METHYLENYLGLYCYL DERIVATIVE" 
_chem_comp.formula                               "C22 H24 Cl N3 O5" 
_chem_comp.formula_weight                        445.896 
_chem_comp.pdbx_release_status                   REF_ONLY 
_chem_comp.type                                  peptide-like 
_chem_comp.pdbx_type                             ? 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    ? 
_chem_comp.pdbx_initial_date                     ? 
_chem_comp.pdbx_modified_date                    ? 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ? 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   ? 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   ? 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_pcm                              ? 
_chem_comp.pdbx_processing_site                  ? 
# 
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_comp_id 
_chem_comp_atom.pdbx_residue_numbering 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_polymer_type 
_chem_comp_atom.pdbx_ref_id 
_chem_comp_atom.pdbx_component_id 
_chem_comp_atom.pdbx_ordinal 
_chem_comp_atom.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
PRD_000334 C1  C1  C  0 1 N N N 5.361  28.086 15.339 3.809  -1.274 -0.639 PHQ 1 C1  polymer 1 1 1  ? ? ? 
PRD_000334 O1  O1  O  0 1 N N N 6.244  27.217 15.096 3.878  -2.138 -1.490 PHQ 1 O1  polymer 1 1 2  ? ? ? 
PRD_000334 O2  O2  O  0 1 N N N 4.106  28.146 14.699 4.931  -0.816 -0.052 PHQ 1 O2  polymer 1 1 3  ? ? ? 
PRD_000334 C2  C2  C  0 1 N N N 3.250  27.375 15.521 6.187  -1.400 -0.486 PHQ 1 C2  polymer 1 1 4  ? ? ? 
PRD_000334 C3  C3  C  0 1 Y N N 1.860  27.998 15.523 7.324  -0.769 0.276  PHQ 1 C3  polymer 1 1 5  ? ? ? 
PRD_000334 C4  C4  C  0 1 Y N N 1.364  28.788 14.464 7.747  -1.321 1.471  PHQ 1 C4  polymer 1 1 6  ? ? ? 
PRD_000334 C5  C5  C  0 1 Y N N 0.076  29.413 14.665 8.790  -0.741 2.169  PHQ 1 C5  polymer 1 1 7  ? ? ? 
PRD_000334 C6  C6  C  0 1 Y N N -0.615 29.345 15.823 9.410  0.389  1.673  PHQ 1 C6  polymer 1 1 8  ? ? ? 
PRD_000334 C7  C7  C  0 1 Y N N -0.068 28.555 16.932 8.989  0.941  0.477  PHQ 1 C7  polymer 1 1 9  ? ? ? 
PRD_000334 C8  C8  C  0 1 Y N N 1.171  27.980 16.730 7.949  0.359  -0.223 PHQ 1 C8  polymer 1 1 10 ? ? ? 
PRD_000334 N1  N1  N  0 1 N N N 5.484  28.853 16.425 2.610  -0.770 -0.286 GLY 2 N   polymer 1 1 11 ? ? ? 
PRD_000334 C9  C9  C  0 1 N N N 6.690  28.798 17.265 1.390  -1.263 -0.929 GLY 2 CA  polymer 1 1 12 ? ? ? 
PRD_000334 C10 C10 C  0 1 N N N 7.993  29.314 16.594 0.195  -0.543 -0.360 GLY 2 C   polymer 1 1 13 ? ? ? 
PRD_000334 O3  O3  O  0 1 N N N 8.041  29.843 15.384 0.348  0.301  0.499  GLY 2 O   polymer 1 1 14 ? ? ? 
PRD_000334 N2  N2  N  0 1 N N N 9.149  29.257 17.284 -1.043 -0.835 -0.804 PHE 3 N   polymer 1 1 15 ? ? ? 
PRD_000334 C11 C11 C  0 1 N N S 10.506 29.781 17.063 -2.205 -0.134 -0.251 PHE 3 CA  polymer 1 1 16 ? ? ? 
PRD_000334 C12 C12 C  0 1 N N N 11.230 28.703 16.174 -3.432 -0.994 -0.409 PHE 3 C   polymer 1 1 17 ? ? ? 
PRD_000334 O4  O4  O  0 1 N N N 11.014 27.514 16.647 -3.345 -2.085 -0.932 PHE 3 O   polymer 1 1 18 ? ? ? 
PRD_000334 C13 C13 C  0 1 N N N 11.122 30.043 18.403 -2.407 1.186  -0.998 PHE 3 CB  polymer 1 1 19 ? ? ? 
PRD_000334 C14 C14 C  0 1 Y N N 10.499 31.266 19.088 -1.233 2.094  -0.739 PHE 3 CG  polymer 1 1 20 ? ? ? 
PRD_000334 C15 C15 C  0 1 Y N N 10.816 32.551 18.513 -0.133 2.057  -1.576 PHE 3 CD1 polymer 1 1 21 ? ? ? 
PRD_000334 C16 C16 C  0 1 Y N N 9.455  31.149 20.000 -1.259 2.969  0.331  PHE 3 CD2 polymer 1 1 22 ? ? ? 
PRD_000334 C17 C17 C  0 1 Y N N 10.190 33.672 19.100 0.944  2.891  -1.338 PHE 3 CE1 polymer 1 1 23 ? ? ? 
PRD_000334 C18 C18 C  0 1 Y N N 8.829  32.269 20.537 -0.182 3.802  0.568  PHE 3 CE2 polymer 1 1 24 ? ? ? 
PRD_000334 C19 C19 C  0 1 Y N N 9.147  33.606 20.061 0.921  3.761  -0.265 PHE 3 CZ  polymer 1 1 25 ? ? ? 
PRD_000334 N3  N3  N  0 1 N N N 11.924 28.971 15.013 -4.627 -0.551 0.032  GLY 4 N   polymer 1 1 26 ? ? ? 
PRD_000334 C20 C20 C  0 1 N N N 12.600 27.947 14.274 -5.820 -1.387 -0.122 GLY 4 CA  polymer 1 1 27 ? ? ? 
PRD_000334 C21 C21 C  0 1 N N N 14.104 28.026 14.509 -7.015 -0.666 0.447  GLY 4 C   polymer 1 1 28 ? ? ? 
PRD_000334 O5  O5  O  0 1 N N N 14.733 27.007 14.020 -6.883 0.432  0.931  GLY 4 O   polymer 1 1 29 ? ? ? 
PRD_000334 C22 C22 C  0 1 N N N 14.927 28.975 15.235 -8.374 -1.316 0.413  0QE 5 C1  polymer 1 1 30 ? ? ? 
PRD_000334 CL1 CL1 CL 0 0 N Y N ?      ?      ?      -9.587 -0.213 1.163  0QE 5 CL1 polymer 1 1 31 ? ? ? 
PRD_000334 H1  H1  H  0 1 N N N 3.192  26.348 15.131 6.174  -2.473 -0.295 PHQ 1 H21 polymer 1 1 32 ? ? ? 
PRD_000334 H2  H2  H  0 1 N N N 3.645  27.355 16.547 6.322  -1.222 -1.553 PHQ 1 H22 polymer 1 1 33 ? ? ? 
PRD_000334 H3  H3  H  0 1 N N N 1.920  28.919 13.547 7.262  -2.204 1.859  PHQ 1 H41 polymer 1 1 34 ? ? ? 
PRD_000334 H4  H4  H  0 1 N N N -0.357 29.965 13.844 9.119  -1.172 3.103  PHQ 1 H51 polymer 1 1 35 ? ? ? 
PRD_000334 H5  H5  H  0 1 N N N -1.556 29.864 15.931 10.225 0.842  2.219  PHQ 1 H61 polymer 1 1 36 ? ? ? 
PRD_000334 H6  H6  H  0 1 N N N -0.607 28.430 17.859 9.474  1.824  0.089  PHQ 1 H71 polymer 1 1 37 ? ? ? 
PRD_000334 H7  H7  H  0 1 N N N 1.637  27.482 17.568 7.622  0.788  -1.159 PHQ 1 H81 polymer 1 1 38 ? ? ? 
PRD_000334 H8  H8  H  0 1 N N N 4.742  29.477 16.672 2.555  -0.080 0.394  GLY 2 H   polymer 1 1 39 ? ? ? 
PRD_000334 H9  H9  H  0 1 N N N 6.506  29.407 18.163 1.446  -1.082 -2.002 GLY 2 HA2 polymer 1 1 40 ? ? ? 
PRD_000334 H10 H10 H  0 1 N N N 6.851  27.750 17.559 1.290  -2.333 -0.746 GLY 2 HA3 polymer 1 1 41 ? ? ? 
PRD_000334 H11 H11 H  0 1 N N N 9.066  28.743 18.138 -1.165 -1.510 -1.491 PHE 3 H   polymer 1 1 42 ? ? ? 
PRD_000334 H12 H12 H  0 1 N N N 10.453 30.722 16.495 -2.037 0.068  0.807  PHE 3 HA  polymer 1 1 43 ? ? ? 
PRD_000334 H13 H13 H  0 1 N N N 10.971 29.161 19.043 -2.487 0.990  -2.067 PHE 3 HB2 polymer 1 1 44 ? ? ? 
PRD_000334 H14 H14 H  0 1 N N N 12.200 30.220 18.271 -3.322 1.665  -0.647 PHE 3 HB3 polymer 1 1 45 ? ? ? 
PRD_000334 H15 H15 H  0 1 N N N 11.495 32.650 17.679 -0.115 1.377  -2.414 PHE 3 HD1 polymer 1 1 46 ? ? ? 
PRD_000334 H16 H16 H  0 1 N N N 9.123  30.166 20.298 -2.120 3.001  0.982  PHE 3 HD2 polymer 1 1 47 ? ? ? 
PRD_000334 H17 H17 H  0 1 N N N 10.529 34.651 18.796 1.804  2.861  -1.991 PHE 3 HE1 polymer 1 1 48 ? ? ? 
PRD_000334 H18 H18 H  0 1 N N N 8.095  32.144 21.320 -0.201 4.486  1.404  PHE 3 HE2 polymer 1 1 49 ? ? ? 
PRD_000334 H19 H19 H  0 1 N N N 8.627  34.485 20.413 1.762  4.412  -0.080 PHE 3 HZ  polymer 1 1 50 ? ? ? 
PRD_000334 H20 H20 H  0 1 N N N 11.956 29.912 14.676 -4.696 0.321  0.450  GLY 4 H   polymer 1 1 51 ? ? ? 
PRD_000334 H21 H21 H  0 1 N N N 12.233 26.963 14.601 -5.988 -1.590 -1.180 GLY 4 HA2 polymer 1 1 52 ? ? ? 
PRD_000334 H22 H22 H  0 1 N N N 12.394 28.078 13.202 -5.675 -2.328 0.410  GLY 4 HA3 polymer 1 1 53 ? ? ? 
PRD_000334 H23 H23 H  0 1 N N N 14.741 29.312 16.265 -8.655 -1.516 -0.621 0QE 5 HA  polymer 1 1 54 ? ? ? 
PRD_000334 H24 H24 H  0 1 N N N 15.740 29.571 14.795 -8.342 -2.254 0.968  0QE 5 HB  polymer 1 1 55 ? ? ? 
# 
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 
PRD_000334 C1  O1  DOUB N N 1  
PRD_000334 C1  O2  SING N N 2  
PRD_000334 O2  C2  SING N N 3  
PRD_000334 C2  C3  SING N N 4  
PRD_000334 C2  H1  SING N N 5  
PRD_000334 C2  H2  SING N N 6  
PRD_000334 C3  C4  DOUB Y N 7  
PRD_000334 C3  C8  SING Y N 8  
PRD_000334 C4  C5  SING Y N 9  
PRD_000334 C4  H3  SING N N 10 
PRD_000334 C5  C6  DOUB Y N 11 
PRD_000334 C5  H4  SING N N 12 
PRD_000334 C6  C7  SING Y N 13 
PRD_000334 C6  H5  SING N N 14 
PRD_000334 C7  C8  DOUB Y N 15 
PRD_000334 C7  H6  SING N N 16 
PRD_000334 C8  H7  SING N N 17 
PRD_000334 N1  C9  SING N N 18 
PRD_000334 N1  H8  SING N N 19 
PRD_000334 C9  C10 SING N N 20 
PRD_000334 C9  H9  SING N N 21 
PRD_000334 C9  H10 SING N N 22 
PRD_000334 C10 O3  DOUB N N 23 
PRD_000334 N2  C11 SING N N 24 
PRD_000334 N2  H11 SING N N 25 
PRD_000334 C11 C12 SING N N 26 
PRD_000334 C11 C13 SING N N 27 
PRD_000334 C11 H12 SING N N 28 
PRD_000334 C12 O4  DOUB N N 29 
PRD_000334 C13 C14 SING N N 30 
PRD_000334 C13 H13 SING N N 31 
PRD_000334 C13 H14 SING N N 32 
PRD_000334 C14 C15 DOUB Y N 33 
PRD_000334 C14 C16 SING Y N 34 
PRD_000334 C15 C17 SING Y N 35 
PRD_000334 C15 H15 SING N N 36 
PRD_000334 C16 C18 DOUB Y N 37 
PRD_000334 C16 H16 SING N N 38 
PRD_000334 C17 C19 DOUB Y N 39 
PRD_000334 C17 H17 SING N N 40 
PRD_000334 C18 C19 SING Y N 41 
PRD_000334 C18 H18 SING N N 42 
PRD_000334 C19 H19 SING N N 43 
PRD_000334 N3  C20 SING N N 44 
PRD_000334 N3  H20 SING N N 45 
PRD_000334 C20 C21 SING N N 46 
PRD_000334 C20 H21 SING N N 47 
PRD_000334 C20 H22 SING N N 48 
PRD_000334 C21 O5  DOUB N N 49 
PRD_000334 C22 CL1 SING N N 50 
PRD_000334 C22 H23 SING N N 51 
PRD_000334 C22 H24 SING N N 52 
PRD_000334 C1  N1  SING N N 53 
PRD_000334 C21 C22 SING N N 54 
PRD_000334 C10 N2  SING N N 55 
PRD_000334 C12 N3  SING N N 56 
# 
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 
PRD_000334 SMILES           ACDLabs              12.01 "ClCC(=O)CNC(=O)C(NC(=O)CNC(=O)OCc1ccccc1)Cc2ccccc2"                                                                                                             
PRD_000334 InChI            InChI                1.03  "InChI=1S/C22H24ClN3O5/c23-12-18(27)13-24-21(29)19(11-16-7-3-1-4-8-16)26-20(28)14-25-22(30)31-15-17-9-5-2-6-10-17/h1-10,19H,11-15H2,(H,24,29)(H,25,30)(H,26,28)" 
PRD_000334 InChIKey         InChI                1.03  HXVSUVCIQJYIIX-UHFFFAOYSA-N                                                                                                                                      
PRD_000334 SMILES_CANONICAL CACTVS               3.370 "ClCC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)OCc2ccccc2"                                                                                                         
PRD_000334 SMILES           CACTVS               3.370 "ClCC(=O)CNC(=O)[CH](Cc1ccccc1)NC(=O)CNC(=O)OCc2ccccc2"                                                                                                          
PRD_000334 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)C[C@@H](C(=O)NCC(=O)CCl)NC(=O)CNC(=O)OCc2ccccc2"                                                                                                      
PRD_000334 SMILES           "OpenEye OEToolkits" 1.7.6 "c1ccc(cc1)CC(C(=O)NCC(=O)CCl)NC(=O)CNC(=O)OCc2ccccc2"                                                                                                           
# 
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 
PRD_000334 "SYSTEMATIC NAME" ACDLabs              12.01 "N-[(benzyloxy)carbonyl]glycyl-N-(3-chloro-2-oxopropyl)-L-phenylalaninamide"                                                                           
PRD_000334 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(phenylmethyl) N-[2-[[(2S)-1-[(3-chloranyl-2-oxidanylidene-propyl)amino]-1-oxidanylidene-3-phenyl-propan-2-yl]amino]-2-oxidanylidene-ethyl]carbamate" 
# 
