data_PRDCC_000553
# 
_chem_comp.id                                    PRD_000553 
_chem_comp.name                                  APSTATIN 
_chem_comp.formula                               "C23 H33 N5 O5" 
_chem_comp.formula_weight                        459.539 
_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_000553 C1  C1  C 0 1 N N R 28.320 56.092 45.216 -3.522 0.400  -0.430 01B 1 CB  polymer 1 1 1  ? ? ? 
PRD_000553 C2  C2  C 0 1 N N S 29.114 56.244 43.906 -3.332 1.866  -0.826 01B 1 CA  polymer 1 1 2  ? ? ? 
PRD_000553 N1  N1  N 0 1 N N N 28.993 55.105 46.117 -2.800 -0.460 -1.378 01B 1 N   polymer 1 1 3  ? ? ? 
PRD_000553 O1  O1  O 0 1 N N N 30.507 56.466 44.181 -3.860 2.078  -2.136 01B 1 O2  polymer 1 1 4  ? ? ? 
PRD_000553 C3  C3  C 0 1 N N N 28.564 57.396 43.080 -1.863 2.203  -0.815 01B 1 C   polymer 1 1 5  ? ? ? 
PRD_000553 C4  C4  C 0 1 N N N 26.882 55.635 44.910 -5.011 0.053  -0.460 01B 1 C6  polymer 1 1 6  ? ? ? 
PRD_000553 C5  C5  C 0 1 Y N N 25.875 55.958 46.001 -5.209 -1.353 0.047  01B 1 C7  polymer 1 1 7  ? ? ? 
PRD_000553 C6  C6  C 0 1 Y N N 24.882 55.041 46.341 -5.175 -2.417 -0.835 01B 1 C8  polymer 1 1 8  ? ? ? 
PRD_000553 C7  C7  C 0 1 Y N N 23.897 55.357 47.285 -5.357 -3.706 -0.371 01B 1 C9  polymer 1 1 9  ? ? ? 
PRD_000553 C8  C8  C 0 1 Y N N 23.904 56.607 47.903 -5.572 -3.931 0.976  01B 1 C10 polymer 1 1 10 ? ? ? 
PRD_000553 C9  C9  C 0 1 Y N N 24.892 57.530 47.578 -5.606 -2.867 1.858  01B 1 C11 polymer 1 1 11 ? ? ? 
PRD_000553 C10 C10 C 0 1 Y N N 25.872 57.204 46.632 -5.420 -1.579 1.394  01B 1 C12 polymer 1 1 12 ? ? ? 
PRD_000553 O2  O2  O 0 1 N N N 28.383 58.506 43.583 -1.256 2.299  -1.861 01B 1 O   polymer 1 1 13 ? ? ? 
PRD_000553 N2  N2  N 0 1 N N N 28.293 57.137 41.790 -1.225 2.398  0.356  PRO 2 N   polymer 1 1 14 ? ? ? 
PRD_000553 C11 C11 C 0 1 N N S 27.768 58.128 40.852 0.175  2.820  0.508  PRO 2 CA  polymer 1 1 15 ? ? ? 
PRD_000553 C12 C12 C 0 1 N N N 26.775 59.114 41.447 1.087  1.817  -0.150 PRO 2 C   polymer 1 1 16 ? ? ? 
PRD_000553 O3  O3  O 0 1 N N N 25.658 58.753 41.812 0.621  0.840  -0.697 PRO 2 O   polymer 1 1 17 ? ? ? 
PRD_000553 C13 C13 C 0 1 N N N 27.169 57.263 39.759 0.472  2.885  2.021  PRO 2 CB  polymer 1 1 18 ? ? ? 
PRD_000553 C14 C14 C 0 1 N N N 28.168 56.152 39.679 -0.608 1.951  2.628  PRO 2 CG  polymer 1 1 19 ? ? ? 
PRD_000553 C15 C15 C 0 1 N N N 28.383 55.813 41.143 -1.816 2.230  1.695  PRO 2 CD  polymer 1 1 20 ? ? ? 
PRD_000553 N3  N3  N 0 1 N N N 27.177 60.390 41.529 2.422  2.006  -0.132 PRO 3 N   polymer 1 1 21 ? ? ? 
PRD_000553 C16 C16 C 0 1 N N S 26.395 61.503 42.065 3.422  1.112  -0.732 PRO 3 CA  polymer 1 1 22 ? ? ? 
PRD_000553 C17 C17 C 0 1 N N N 24.892 61.388 41.801 3.320  -0.259 -0.115 PRO 3 C   polymer 1 1 23 ? ? ? 
PRD_000553 O4  O4  O 0 1 N N N 24.448 61.441 40.659 2.493  -0.477 0.745  PRO 3 O   polymer 1 1 24 ? ? ? 
PRD_000553 C18 C18 C 0 1 N N N 27.015 62.705 41.367 4.812  1.716  -0.440 PRO 3 CB  polymer 1 1 25 ? ? ? 
PRD_000553 C19 C19 C 0 1 N N N 28.448 62.332 41.311 4.545  2.618  0.794  PRO 3 CG  polymer 1 1 26 ? ? ? 
PRD_000553 C20 C20 C 0 1 N N N 28.378 60.901 40.843 3.120  3.147  0.489  PRO 3 CD  polymer 1 1 27 ? ? ? 
PRD_000553 N4  N4  N 0 1 N N N 24.119 61.230 42.870 4.147  -1.244 -0.518 ALA 4 N   polymer 1 1 28 ? ? ? 
PRD_000553 C21 C21 C 0 1 N N S 22.671 61.117 42.767 4.048  -2.576 0.082  ALA 4 CA  polymer 1 1 29 ? ? ? 
PRD_000553 C22 C22 C 0 1 N N N 22.022 62.433 43.201 5.373  -3.283 -0.041 ALA 4 C   polymer 1 1 30 ? ? ? 
PRD_000553 O5  O5  O 0 1 N N N 21.763 63.319 42.376 6.309  -2.727 -0.577 ALA 4 O   polymer 1 1 31 ? ? ? 
PRD_000553 C23 C23 C 0 1 N N N 22.173 59.977 43.627 2.971  -3.384 -0.646 ALA 4 CB  polymer 1 1 32 ? ? ? 
PRD_000553 N5  N5  N 0 1 N N N 21.769 62.585 44.494 5.519  -4.531 0.445  NH2 5 N   polymer 1 1 33 ? ? ? 
PRD_000553 H1  H1  H 0 1 N N N 28.279 57.070 45.718 -3.131 0.242  0.575  01B 1 HB  polymer 1 1 34 ? ? ? 
PRD_000553 H2  H2  H 0 1 N N N 28.998 55.316 43.326 -3.856 2.505  -0.115 01B 1 HA  polymer 1 1 35 ? ? ? 
PRD_000553 H3  H3  H 0 1 N N N 28.469 55.015 46.964 -3.144 -0.331 -2.318 01B 1 H   polymer 1 1 36 ? ? ? 
PRD_000553 H4  H4  H 0 0 N Y N 29.043 54.217 45.660 -1.805 -0.294 -1.331 01B 1 H2  polymer 1 1 37 ? ? ? 
PRD_000553 H5  H5  H 0 1 N N N 30.981 56.557 43.363 -3.440 1.541  -2.822 01B 1 HO2 polymer 1 1 38 ? ? ? 
PRD_000553 H6  H6  H 0 1 N N N 26.554 56.128 43.983 -5.559 0.749  0.176  01B 1 H6  polymer 1 1 39 ? ? ? 
PRD_000553 H7  H7  H 0 1 N N N 26.892 54.545 44.762 -5.382 0.126  -1.482 01B 1 H6A polymer 1 1 40 ? ? ? 
PRD_000553 H8  H8  H 0 1 N N N 24.872 54.070 45.868 -5.007 -2.240 -1.887 01B 1 H8  polymer 1 1 41 ? ? ? 
PRD_000553 H9  H9  H 0 1 N N N 23.134 54.634 47.534 -5.331 -4.537 -1.060 01B 1 H9  polymer 1 1 42 ? ? ? 
PRD_000553 H10 H10 H 0 1 N N N 23.146 56.857 48.630 -5.715 -4.938 1.339  01B 1 H10 polymer 1 1 43 ? ? ? 
PRD_000553 H11 H11 H 0 1 N N N 24.904 58.499 48.055 -5.775 -3.043 2.910  01B 1 H11 polymer 1 1 44 ? ? ? 
PRD_000553 H12 H12 H 0 1 N N N 26.636 57.927 46.387 -5.442 -0.748 2.084  01B 1 H12 polymer 1 1 45 ? ? ? 
PRD_000553 H13 H13 H 0 1 N N N 28.606 58.697 40.423 0.318  3.802  0.057  PRO 2 HA  polymer 1 1 46 ? ? ? 
PRD_000553 H14 H14 H 0 1 N N N 26.174 56.889 40.042 1.472  2.508  2.235  PRO 2 HB2 polymer 1 1 47 ? ? ? 
PRD_000553 H15 H15 H 0 1 N N N 27.098 57.810 38.807 0.355  3.903  2.394  PRO 2 HB3 polymer 1 1 48 ? ? ? 
PRD_000553 H16 H16 H 0 1 N N N 27.765 55.292 39.125 -0.299 0.907  2.570  PRO 2 HG2 polymer 1 1 49 ? ? ? 
PRD_000553 H17 H17 H 0 1 N N N 29.102 56.488 39.205 -0.837 2.233  3.655  PRO 2 HG3 polymer 1 1 50 ? ? ? 
PRD_000553 H18 H18 H 0 1 N N N 29.371 55.357 41.305 -2.331 3.141  2.000  PRO 2 HD2 polymer 1 1 51 ? ? ? 
PRD_000553 H19 H19 H 0 1 N N N 27.600 55.135 41.514 -2.504 1.384  1.703  PRO 2 HD3 polymer 1 1 52 ? ? ? 
PRD_000553 H20 H20 H 0 1 N N N 26.562 61.591 43.149 3.263  1.046  -1.808 PRO 3 HA  polymer 1 1 53 ? ? ? 
PRD_000553 H21 H21 H 0 1 N N N 26.598 62.839 40.358 5.530  0.933  -0.197 PRO 3 HB2 polymer 1 1 54 ? ? ? 
PRD_000553 H22 H22 H 0 1 N N N 26.865 63.626 41.950 5.159  2.311  -1.284 PRO 3 HB3 polymer 1 1 55 ? ? ? 
PRD_000553 H23 H23 H 0 1 N N N 28.998 62.961 40.595 4.561  2.035  1.715  PRO 3 HG2 polymer 1 1 56 ? ? ? 
PRD_000553 H24 H24 H 0 1 N N N 28.920 62.406 42.302 5.263  3.438  0.841  PRO 3 HG3 polymer 1 1 57 ? ? ? 
PRD_000553 H25 H25 H 0 1 N N N 29.275 60.341 41.146 3.164  3.987  -0.205 PRO 3 HD2 polymer 1 1 58 ? ? ? 
PRD_000553 H26 H26 H 0 1 N N N 28.263 60.847 39.750 2.619  3.442  1.411  PRO 3 HD3 polymer 1 1 59 ? ? ? 
PRD_000553 H27 H27 H 0 1 N N N 24.545 61.187 43.774 4.809  -1.070 -1.206 ALA 4 H   polymer 1 1 60 ? ? ? 
PRD_000553 H28 H28 H 0 1 N N N 22.392 60.919 41.722 3.782  -2.482 1.135  ALA 4 HA  polymer 1 1 61 ? ? ? 
PRD_000553 H29 H29 H 0 1 N N N 21.079 59.902 43.540 3.236  -3.478 -1.699 ALA 4 HB1 polymer 1 1 62 ? ? ? 
PRD_000553 H30 H30 H 0 1 N N N 22.632 59.036 43.290 2.897  -4.376 -0.199 ALA 4 HB2 polymer 1 1 63 ? ? ? 
PRD_000553 H31 H31 H 0 1 N N N 22.446 60.163 44.676 2.012  -2.873 -0.557 ALA 4 HB3 polymer 1 1 64 ? ? ? 
PRD_000553 H32 H32 H 0 1 N N N 21.358 63.434 44.827 4.771  -4.976 0.873  NH2 5 HN1 polymer 1 1 65 ? ? ? 
PRD_000553 H33 H33 H 0 1 N N N 21.990 61.851 45.136 6.372  -4.986 0.366  NH2 5 HN2 polymer 1 1 66 ? ? ? 
# 
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_000553 N1  C1  SING N N 1  
PRD_000553 C2  C1  SING N N 2  
PRD_000553 C1  C4  SING N N 3  
PRD_000553 C1  H1  SING N N 4  
PRD_000553 O1  C2  SING N N 5  
PRD_000553 C2  C3  SING N N 6  
PRD_000553 C2  H2  SING N N 7  
PRD_000553 N1  H3  SING N N 8  
PRD_000553 N1  H4  SING N N 9  
PRD_000553 O1  H5  SING N N 10 
PRD_000553 C3  O2  DOUB N N 11 
PRD_000553 C4  C5  SING N N 12 
PRD_000553 C4  H6  SING N N 13 
PRD_000553 C4  H7  SING N N 14 
PRD_000553 C6  C5  DOUB Y N 15 
PRD_000553 C5  C10 SING Y N 16 
PRD_000553 C6  C7  SING Y N 17 
PRD_000553 C6  H8  SING N N 18 
PRD_000553 C7  C8  DOUB Y N 19 
PRD_000553 C7  H9  SING N N 20 
PRD_000553 C8  C9  SING Y N 21 
PRD_000553 C8  H10 SING N N 22 
PRD_000553 C10 C9  DOUB Y N 23 
PRD_000553 C9  H11 SING N N 24 
PRD_000553 C10 H12 SING N N 25 
PRD_000553 N2  C11 SING N N 26 
PRD_000553 N2  C15 SING N N 27 
PRD_000553 C11 C12 SING N N 28 
PRD_000553 C11 C13 SING N N 29 
PRD_000553 C11 H13 SING N N 30 
PRD_000553 C12 O3  DOUB N N 31 
PRD_000553 C13 C14 SING N N 32 
PRD_000553 C13 H14 SING N N 33 
PRD_000553 C13 H15 SING N N 34 
PRD_000553 C14 C15 SING N N 35 
PRD_000553 C14 H16 SING N N 36 
PRD_000553 C14 H17 SING N N 37 
PRD_000553 C15 H18 SING N N 38 
PRD_000553 C15 H19 SING N N 39 
PRD_000553 N3  C16 SING N N 40 
PRD_000553 N3  C20 SING N N 41 
PRD_000553 C16 C17 SING N N 42 
PRD_000553 C16 C18 SING N N 43 
PRD_000553 C16 H20 SING N N 44 
PRD_000553 C17 O4  DOUB N N 45 
PRD_000553 C18 C19 SING N N 46 
PRD_000553 C18 H21 SING N N 47 
PRD_000553 C18 H22 SING N N 48 
PRD_000553 C19 C20 SING N N 49 
PRD_000553 C19 H23 SING N N 50 
PRD_000553 C19 H24 SING N N 51 
PRD_000553 C20 H25 SING N N 52 
PRD_000553 C20 H26 SING N N 53 
PRD_000553 N4  C21 SING N N 54 
PRD_000553 N4  H27 SING N N 55 
PRD_000553 C21 C22 SING N N 56 
PRD_000553 C21 C23 SING N N 57 
PRD_000553 C21 H28 SING N N 58 
PRD_000553 C22 O5  DOUB N N 59 
PRD_000553 C23 H29 SING N N 60 
PRD_000553 C23 H30 SING N N 61 
PRD_000553 C23 H31 SING N N 62 
PRD_000553 N5  H32 SING N N 63 
PRD_000553 N5  H33 SING N N 64 
PRD_000553 C3  N2  SING N N 65 
PRD_000553 N5  C22 SING N N 66 
PRD_000553 C12 N3  SING N N 67 
PRD_000553 C17 N4  SING N N 68 
# 
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_000553 SMILES           ACDLabs              12.01 "O=C(N1C(C(=O)NC(C(=O)N)C)CCC1)C3N(C(=O)C(O)C(N)Cc2ccccc2)CCC3"                                                                                                                       
PRD_000553 InChI            InChI                1.03  "InChI=1S/C23H33N5O5/c1-14(20(25)30)26-21(31)17-9-5-11-27(17)22(32)18-10-6-12-28(18)23(33)19(29)16(24)13-15-7-3-2-4-8-15/h2-4,7-8,14,16-19,29H,5-6,9-13,24H2,1H3,(H2,25,30)(H,26,31)" 
PRD_000553 InChIKey         InChI                1.03  YVUUZAPYLPWFHE-UHFFFAOYSA-N                                                                                                                                                           
PRD_000553 SMILES_CANONICAL CACTVS               3.370 "C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)[C@@H](O)[C@H](N)Cc3ccccc3)C(N)=O"                                                                                                    
PRD_000553 SMILES           CACTVS               3.370 "C[CH](NC(=O)[CH]1CCCN1C(=O)[CH]2CCCN2C(=O)[CH](O)[CH](N)Cc3ccccc3)C(N)=O"                                                                                                            
PRD_000553 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](Cc3ccccc3)N)O"                                                                                                   
PRD_000553 SMILES           "OpenEye OEToolkits" 1.7.6 "CC(C(=O)N)NC(=O)C1CCCN1C(=O)C2CCCN2C(=O)C(C(Cc3ccccc3)N)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 
PRD_000553 "SYSTEMATIC NAME" ACDLabs              12.01 "1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-prolyl-L-prolyl-L-alaninamide"                                                                                 
PRD_000553 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S)-N-[(2S)-1-azanyl-1-oxidanylidene-propan-2-yl]-1-[(2S)-1-[(2S,3R)-3-azanyl-2-oxidanyl-4-phenyl-butanoyl]pyrrolidin-2-yl]carbonyl-pyrrolidine-2-carboxamide" 
# 
