data_X22
# 
_chem_comp.id                                    X22 
_chem_comp.name                                  (3S,6S,7S,9aS)-6-{[(2S)-2-aminobutanoyl]amino}-N-(diphenylmethyl)-7-(hydroxymethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H36 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2(S),3(S),6(S),7(S),9a(S) 6-(2-Amino-butyrylamino)-7-hydroxymethyl-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid benzhydryl-amide" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-03-21 
_chem_comp.pdbx_modified_date                    2008-10-24 
_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                        492.610 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     X22 
_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        3CLX 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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 
X22 CAA  CAA  C 0 1 N N N -12.168 44.198 -33.205 -0.415 3.443  -2.869 CAA  X22 1  
X22 CB   CB   C 0 1 N N N -13.199 45.233 -32.767 -0.827 2.631  -1.640 CB   X22 2  
X22 CA   CA   C 0 1 N N S -12.676 46.676 -32.597 -2.276 2.958  -1.275 CA   X22 3  
X22 N    N    N 0 1 N N N -13.158 47.508 -33.700 -2.371 4.364  -0.861 N    X22 4  
X22 C    C    C 0 1 N N N -11.153 46.807 -32.500 -2.722 2.069  -0.143 C    X22 5  
X22 O    O    O 0 1 N N N -10.427 46.727 -33.493 -2.735 2.495  0.993  O    X22 6  
X22 NAX  NAX  N 0 1 N N N -10.721 47.044 -31.267 -3.107 0.802  -0.392 NAX  X22 7  
X22 CBI  CBI  C 0 1 N N S -9.295  47.211 -30.948 -3.536 -0.052 0.697  CBI  X22 8  
X22 CBA  CBA  C 0 1 N N N -8.804  46.057 -30.025 -2.359 -0.724 1.371  CBA  X22 9  
X22 OAE  OAE  O 0 1 N N N -9.629  45.236 -29.618 -2.040 -0.404 2.485  OAE  X22 10 
X22 NBJ  NBJ  N 0 1 N N N -7.512  45.896 -29.679 -1.671 -1.686 0.710  NBJ  X22 11 
X22 CBE  CBE  C 0 1 N N S -9.014  48.669 -30.466 -4.527 -1.132 0.240  CBE  X22 12 
X22 CAR  CAR  C 0 1 N N N -9.774  49.072 -29.190 -5.956 -0.605 0.399  CAR  X22 13 
X22 OAF  OAF  O 0 1 N N N -11.019 49.679 -29.572 -6.885 -1.645 0.087  OAF  X22 14 
X22 CAS  CAS  C 0 1 N N N -7.505  49.034 -30.382 -4.265 -1.489 -1.221 CAS  X22 15 
X22 CAT  CAT  C 0 1 N N N -6.621  48.143 -29.487 -2.805 -1.817 -1.495 CAT  X22 16 
X22 CBF  CBF  C 0 1 N N S -6.392  46.759 -30.100 -2.191 -2.574 -0.324 CBF  X22 17 
X22 CAU  CAU  C 0 1 N N N -5.131  46.141 -29.501 -0.988 -3.394 -0.829 CAU  X22 18 
X22 CAV  CAV  C 0 1 N N N -5.521  44.697 -29.214 -0.075 -3.426 0.415  CAV  X22 19 
X22 CBG  CBG  C 0 1 N N S -7.012  44.770 -28.850 -0.261 -2.006 0.974  CBG  X22 20 
X22 CAZ  CAZ  C 0 1 N N N -7.162  44.858 -27.306 0.643  -1.036 0.262  CAZ  X22 21 
X22 OAD  OAD  O 0 1 N N N -7.709  45.799 -26.727 0.168  -0.148 -0.413 OAD  X22 22 
X22 NAW  NAW  N 0 1 N N N -6.629  43.770 -26.734 1.981  -1.156 0.373  NAW  X22 23 
X22 CBH  CBH  C 0 1 N N N -6.483  43.340 -25.310 2.861  -0.212 -0.321 CBH  X22 24 
X22 CBC  CBC  C 0 1 Y N N -6.051  44.423 -24.309 3.045  1.020  0.528  CBC  X22 25 
X22 CAO  CAO  C 0 1 Y N N -4.679  44.624 -24.128 3.062  2.270  -0.063 CAO  X22 26 
X22 CAK  CAK  C 0 1 Y N N -4.214  45.577 -23.228 3.231  3.400  0.715  CAK  X22 27 
X22 CAH  CAH  C 0 1 Y N N -5.133  46.321 -22.498 3.382  3.280  2.084  CAH  X22 28 
X22 CAL  CAL  C 0 1 Y N N -6.506  46.115 -22.665 3.364  2.030  2.675  CAL  X22 29 
X22 CAP  CAP  C 0 1 Y N N -6.974  45.163 -23.572 3.191  0.901  1.897  CAP  X22 30 
X22 CBB  CBB  C 0 1 Y N N -7.640  42.440 -24.806 4.200  -0.859 -0.563 CBB  X22 31 
X22 CAM  CAM  C 0 1 Y N N -7.405  41.600 -23.710 4.860  -0.655 -1.761 CAM  X22 32 
X22 CAI  CAI  C 0 1 Y N N -8.411  40.758 -23.237 6.088  -1.248 -1.984 CAI  X22 33 
X22 CAG  CAG  C 0 1 Y N N -9.650  40.742 -23.870 6.657  -2.046 -1.009 CAG  X22 34 
X22 CAJ  CAJ  C 0 1 Y N N -9.883  41.566 -24.969 5.998  -2.250 0.189  CAJ  X22 35 
X22 CAN  CAN  C 0 1 Y N N -8.882  42.413 -25.442 4.772  -1.653 0.414  CAN  X22 36 
X22 HAA  HAA  H 0 1 N N N -11.920 44.353 -34.265 0.618  3.210  -3.129 HAA  X22 37 
X22 HAAA HAAA H 0 0 N N N -11.258 44.306 -32.596 -1.066 3.192  -3.706 HAAA X22 38 
X22 HAAB HAAB H 0 0 N N N -12.582 43.188 -33.069 -0.502 4.507  -2.647 HAAB X22 39 
X22 HB   HB   H 0 1 N N N -13.987 45.257 -33.534 -0.740 1.567  -1.862 HB   X22 40 
X22 HBA  HBA  H 0 1 N N N -13.539 44.916 -31.770 -0.176 2.882  -0.803 HBA  X22 41 
X22 HA   HA   H 0 1 N N N -13.071 47.015 -31.628 -2.916 2.791  -2.142 HA   X22 42 
X22 HN   HN   H 0 1 N N N -13.268 48.450 -33.384 -3.329 4.623  -0.676 HN   X22 43 
X22 HNA  HNA  H 0 1 N N N -12.497 47.483 -34.450 -1.786 4.545  -0.058 HNA  X22 44 
X22 HNAX HNAX H 0 0 N N N -11.391 47.111 -30.527 -3.097 0.462  -1.300 HNAX X22 45 
X22 HBI  HBI  H 0 1 N N N -8.671  47.107 -31.848 -4.040 0.564  1.454  HBI  X22 46 
X22 HBE  HBE  H 0 1 N N N -9.432  49.285 -31.276 -4.401 -2.017 0.868  HBE  X22 47 
X22 HAR  HAR  H 0 1 N N N -9.968  48.181 -28.575 -6.110 -0.277 1.427  HAR  X22 48 
X22 HARA HARA H 0 0 N N N -9.174  49.783 -28.604 -6.111 0.235  -0.277 HARA X22 49 
X22 HOAF HOAF H 0 0 N N N -11.556 49.813 -28.800 -7.812 -1.381 0.166  HOAF X22 50 
X22 HAS  HAS  H 0 1 N N N -7.100  48.969 -31.403 -4.878 -2.361 -1.486 HAS  X22 51 
X22 HASA HASA H 0 0 N N N -7.472  50.033 -29.922 -4.583 -0.664 -1.865 HASA X22 52 
X22 HAT  HAT  H 0 1 N N N -5.646  48.635 -29.356 -2.753 -2.461 -2.388 HAT  X22 53 
X22 HATA HATA H 0 0 N N N -7.137  48.008 -28.525 -2.227 -0.923 -1.711 HATA X22 54 
X22 HBF  HBF  H 0 1 N N N -6.308  46.846 -31.193 -2.939 -3.255 0.107  HBF  X22 55 
X22 HAU  HAU  H 0 1 N N N -4.288  46.194 -30.205 -1.298 -4.404 -1.114 HAU  X22 56 
X22 HAUA HAUA H 0 0 N N N -4.794  46.671 -28.598 -0.498 -2.900 -1.671 HAUA X22 57 
X22 HAV  HAV  H 0 1 N N N -5.357  44.058 -30.094 -0.418 -4.172 1.132  HAV  X22 58 
X22 HAVA HAVA H 0 0 N N N -4.916  44.253 -28.410 0.962  -3.603 0.136  HAVA X22 59 
X22 HBG  HBG  H 0 1 N N N -7.629  43.888 -29.078 -0.064 -1.993 2.045  HBG  X22 60 
X22 HNAW HNAW H 0 0 N N N -6.254  43.115 -27.390 2.361  -1.866 0.913  HNAW X22 61 
X22 HBH  HBH  H 0 1 N N N -5.596  42.691 -25.348 2.414  0.067  -1.275 HBH  X22 62 
X22 HAO  HAO  H 0 1 N N N -3.973  44.033 -24.693 2.944  2.363  -1.132 HAO  X22 63 
X22 HAK  HAK  H 0 1 N N N -3.154  45.737 -23.098 3.245  4.376  0.254  HAK  X22 64 
X22 HAH  HAH  H 0 1 N N N -4.784  47.064 -21.796 3.515  4.163  2.692  HAH  X22 65 
X22 HAL  HAL  H 0 1 N N N -7.209  46.697 -22.088 3.483  1.937  3.744  HAL  X22 66 
X22 HAP  HAP  H 0 1 N N N -8.034  45.002 -23.701 3.173  -0.075 2.359  HAP  X22 67 
X22 HAM  HAM  H 0 1 N N N -6.438  41.604 -23.228 4.415  -0.031 -2.523 HAM  X22 68 
X22 HAI  HAI  H 0 1 N N N -8.229  40.122 -22.384 6.603  -1.089 -2.919 HAI  X22 69 
X22 HAG  HAG  H 0 1 N N N -10.432 40.090 -23.509 7.616  -2.511 -1.183 HAG  X22 70 
X22 HAJ  HAJ  H 0 1 N N N -10.846 41.548 -25.458 6.442  -2.874 0.951  HAJ  X22 71 
X22 HAN  HAN  H 0 1 N N N -9.067  43.046 -26.297 4.258  -1.809 1.351  HAN  X22 72 
# 
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 
X22 CAA CB   SING N N 1  
X22 CB  CA   SING N N 2  
X22 CA  N    SING N N 3  
X22 CA  C    SING N N 4  
X22 C   O    DOUB N N 5  
X22 C   NAX  SING N N 6  
X22 NAX CBI  SING N N 7  
X22 CBI CBA  SING N N 8  
X22 CBI CBE  SING N N 9  
X22 CBA OAE  DOUB N N 10 
X22 CBA NBJ  SING N N 11 
X22 NBJ CBF  SING N N 12 
X22 NBJ CBG  SING N N 13 
X22 CBE CAR  SING N N 14 
X22 CBE CAS  SING N N 15 
X22 CAR OAF  SING N N 16 
X22 CAS CAT  SING N N 17 
X22 CAT CBF  SING N N 18 
X22 CBF CAU  SING N N 19 
X22 CAU CAV  SING N N 20 
X22 CAV CBG  SING N N 21 
X22 CBG CAZ  SING N N 22 
X22 CAZ OAD  DOUB N N 23 
X22 CAZ NAW  SING N N 24 
X22 NAW CBH  SING N N 25 
X22 CBH CBC  SING N N 26 
X22 CBH CBB  SING N N 27 
X22 CBC CAO  DOUB N N 28 
X22 CBC CAP  SING N N 29 
X22 CAO CAK  SING N N 30 
X22 CAK CAH  DOUB N N 31 
X22 CAH CAL  SING N N 32 
X22 CAL CAP  DOUB N N 33 
X22 CBB CAM  DOUB N N 34 
X22 CBB CAN  SING N N 35 
X22 CAM CAI  SING N N 36 
X22 CAI CAG  DOUB N N 37 
X22 CAG CAJ  SING N N 38 
X22 CAJ CAN  DOUB N N 39 
X22 CAA HAA  SING N N 40 
X22 CAA HAAA SING N N 41 
X22 CAA HAAB SING N N 42 
X22 CB  HB   SING N N 43 
X22 CB  HBA  SING N N 44 
X22 CA  HA   SING N N 45 
X22 N   HN   SING N N 46 
X22 N   HNA  SING N N 47 
X22 NAX HNAX SING N N 48 
X22 CBI HBI  SING N N 49 
X22 CBE HBE  SING N N 50 
X22 CAR HAR  SING N N 51 
X22 CAR HARA SING N N 52 
X22 OAF HOAF SING N N 53 
X22 CAS HAS  SING Y N 54 
X22 CAS HASA SING Y N 55 
X22 CAT HAT  SING Y N 56 
X22 CAT HATA SING N N 57 
X22 CBF HBF  SING Y N 58 
X22 CAU HAU  SING N N 59 
X22 CAU HAUA SING Y N 60 
X22 CAV HAV  SING N N 61 
X22 CAV HAVA SING Y N 62 
X22 CBG HBG  SING N N 63 
X22 NAW HNAW SING N N 64 
X22 CBH HBH  SING Y N 65 
X22 CAO HAO  SING Y N 66 
X22 CAK HAK  SING Y N 67 
X22 CAH HAH  SING N N 68 
X22 CAL HAL  SING Y N 69 
X22 CAP HAP  SING N N 70 
X22 CAM HAM  SING Y N 71 
X22 CAI HAI  SING N N 72 
X22 CAG HAG  SING Y N 73 
X22 CAJ HAJ  SING N N 74 
X22 CAN HAN  SING N N 75 
# 
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 
X22 SMILES           ACDLabs              10.04 O=C(NC(c1ccccc1)c2ccccc2)C4N3C(=O)C(NC(=O)C(N)CC)C(CCC3CC4)CO 
X22 InChI            InChI                1.02b 
InChI=1/C28H36N4O4/c1-2-22(29)26(34)31-25-20(17-33)13-14-21-15-16-23(32(21)28(25)36)27(35)30-24(18-9-5-3-6-10-18)19-11-7-4-8-12-19/h3-12,20-25,33H,2,13-17,29H2,1H3,(H,30,35)(H,31,34)/t20-,21+,22+,23+,25+/m1/s1/f/h30-31H 
X22 InChIKey         InChI                1.02b WXYVFFGXHFXTLU-YOLVKQTKDB 
X22 SMILES_CANONICAL CACTVS               3.341 CC[C@H](N)C(=O)N[C@H]1[C@@H](CO)CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4 
X22 SMILES           CACTVS               3.341 CC[CH](N)C(=O)N[CH]1[CH](CO)CC[CH]2CC[CH](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4 
X22 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H](C(=O)N[C@H]1[C@H](CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4)CO)N 
X22 SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C(=O)NC1C(CCC2CCC(N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4)CO)N 
# 
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 
X22 "SYSTEMATIC NAME" ACDLabs              10.04 (3S,6S,7S,9aS)-6-{[(2S)-2-aminobutanoyl]amino}-N-(diphenylmethyl)-7-(hydroxymethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamide         
X22 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (3S,6S,7S,9aS)-6-[[(2S)-2-aminobutanoyl]amino]-N-benzhydryl-7-(hydroxymethyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[5,1-g]azepine-3-carboxamide 
# 
