data_ATN
# 
_chem_comp.id                                    ATN 
_chem_comp.name                                  N-[(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTANOYL]-L-PROLYL-L-PROLYL-L-ALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H33 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         APSTATIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-11-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        459.539 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ATN 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1N51 
_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 
ATN O1   O1   O 0 1 N N N 30.507 56.466 44.181 -2.892 -1.363 2.826  O1   ATN 1  
ATN C1   C1   C 0 1 N N S 29.114 56.244 43.906 -2.784 -1.602 1.421  C1   ATN 2  
ATN CB   CB   C 0 1 N N N 26.882 55.635 44.910 -4.714 -0.059 1.050  CB   ATN 3  
ATN CG   CG   C 0 1 Y N N 25.875 55.958 46.001 -5.231 1.078  0.207  CG   ATN 4  
ATN CD1  CD1  C 0 1 Y N N 25.872 57.204 46.632 -5.859 0.817  -0.996 CD1  ATN 5  
ATN CD2  CD2  C 0 1 Y N N 24.882 55.041 46.341 -5.083 2.382  0.641  CD2  ATN 6  
ATN CE1  CE1  C 0 1 Y N N 24.892 57.530 47.578 -6.333 1.861  -1.769 CE1  ATN 7  
ATN CE2  CE2  C 0 1 Y N N 23.897 55.357 47.285 -5.553 3.426  -0.134 CE2  ATN 8  
ATN CZ   CZ   C 0 1 Y N N 23.904 56.607 47.903 -6.180 3.165  -1.338 CZ   ATN 9  
ATN C    C    C 0 1 N N N 28.564 57.396 43.080 -1.346 -1.881 1.068  C    ATN 10 
ATN O    O    O 0 1 N N N 28.383 58.506 43.583 -0.468 -1.651 1.872  O    ATN 11 
ATN N    N    N 0 1 N N N 28.993 55.105 46.117 -2.414 0.779  0.986  N    ATN 12 
ATN CA   CA   C 0 1 N N R 28.320 56.092 45.216 -3.268 -0.369 0.656  CA   ATN 13 
ATN N1   N1   N 0 1 N N N 28.293 57.137 41.790 -1.035 -2.385 -0.143 N1   ATN 14 
ATN CA1  CA1  C 0 1 N N S 27.768 58.128 40.852 0.325  -2.675 -0.632 CA1  ATN 15 
ATN C2   C2   C 0 1 N N N 26.775 59.114 41.447 1.293  -1.629 -0.140 C2   ATN 16 
ATN O2   O2   O 0 1 N N N 25.658 58.753 41.812 0.906  -0.501 0.082  O2   ATN 17 
ATN CB1  CB1  C 0 1 N N N 27.169 57.263 39.759 0.214  -2.623 -2.176 CB1  ATN 18 
ATN CG1  CG1  C 0 1 N N N 28.168 56.152 39.679 -1.188 -3.247 -2.408 CG1  ATN 19 
ATN CD   CD   C 0 1 N N N 28.383 55.813 41.143 -1.999 -2.736 -1.199 CD   ATN 20 
ATN N2   N2   N 0 1 N N N 27.177 60.390 41.529 2.588  -1.948 0.053  N2   ATN 21 
ATN CA2  CA2  C 0 1 N N S 26.395 61.503 42.065 3.661  -1.005 0.419  CA2  ATN 22 
ATN C3   C3   C 0 1 N N N 24.892 61.388 41.801 3.455  0.318  -0.272 C3   ATN 23 
ATN O3   O3   O 0 1 N N N 24.448 61.441 40.659 2.866  0.364  -1.332 O3   ATN 24 
ATN CB2  CB2  C 0 1 N N N 27.015 62.705 41.367 4.967  -1.675 -0.078 CB2  ATN 25 
ATN CG2  CG2  C 0 1 N N N 28.448 62.332 41.311 4.680  -3.171 0.214  CG2  ATN 26 
ATN CD3  CD3  C 0 1 N N N 28.378 60.901 40.843 3.168  -3.295 -0.070 CD3  ATN 27 
ATN N3   N3   N 0 1 N N N 24.119 61.230 42.870 3.925  1.451  0.287  N3   ATN 28 
ATN CA3  CA3  C 0 1 N N S 22.671 61.117 42.767 3.724  2.737  -0.385 CA3  ATN 29 
ATN C4   C4   C 0 1 N N N 22.022 62.433 43.201 4.795  3.704  0.051  C4   ATN 30 
ATN O4   O4   O 0 1 N N N 21.763 63.319 42.376 5.642  3.353  0.845  O4   ATN 31 
ATN CB3  CB3  C 0 1 N N N 22.173 59.977 43.627 2.350  3.298  -0.014 CB3  ATN 32 
ATN N4   N4   N 0 1 N N N 21.769 62.585 44.494 4.812  4.958  -0.441 N4   ATN 33 
ATN HO1  HO1  H 0 1 N N N 30.988 56.515 43.363 -2.335 -0.597 3.023  HO1  ATN 34 
ATN HC1  HC1  H 0 1 N N N 29.009 55.311 43.333 -3.398 -2.462 1.151  HC1  ATN 35 
ATN HB1  1HB  H 0 1 N N N 26.561 56.181 44.011 -5.332 -0.942 0.887  HB1  ATN 36 
ATN HB2  2HB  H 0 1 N N N 26.896 54.543 44.777 -4.751 0.222  2.102  HB2  ATN 37 
ATN HD1  HD1  H 0 1 N N N 26.636 57.927 46.387 -5.978 -0.202 -1.333 HD1  ATN 38 
ATN HD2  HD2  H 0 1 N N N 24.872 54.070 45.868 -4.593 2.586  1.582  HD2  ATN 39 
ATN HE1  HE1  H 0 1 N N N 24.904 58.499 48.055 -6.823 1.657  -2.710 HE1  ATN 40 
ATN HE2  HE2  H 0 1 N N N 23.134 54.634 47.534 -5.433 4.445  0.203  HE2  ATN 41 
ATN HZ   HZ   H 0 1 N N N 23.146 56.857 48.630 -6.550 3.980  -1.942 HZ   ATN 42 
ATN HN1  1HN  H 0 1 N N N 29.872 55.474 46.418 -2.492 0.921  1.982  HN1  ATN 43 
ATN HN2  2HN  H 0 1 N N N 29.143 54.249 45.622 -1.462 0.493  0.808  HN2  ATN 44 
ATN HA   HA   H 0 1 N N N 28.284 57.067 45.725 -3.217 -0.564 -0.415 HA   ATN 45 
ATN HA1  HA1  H 0 1 N N N 28.553 58.811 40.496 0.642  -3.666 -0.307 HA1  ATN 46 
ATN HB11 1HB1 H 0 0 N N N 27.013 57.792 38.807 0.248  -1.595 -2.536 HB11 ATN 47 
ATN HB12 2HB1 H 0 0 N N N 26.163 56.901 40.019 0.992  -3.225 -2.644 HB12 ATN 48 
ATN HG11 1HG1 H 0 0 N N N 29.092 56.429 39.151 -1.620 -2.888 -3.342 HG11 ATN 49 
ATN HG12 2HG1 H 0 0 N N N 27.785 55.293 39.109 -1.131 -4.336 -2.402 HG12 ATN 50 
ATN HD1A 1HD  H 0 0 N N N 27.657 55.085 41.534 -2.575 -1.855 -1.485 HD1A ATN 51 
ATN HD2A 2HD  H 0 0 N N N 29.360 55.337 41.315 -2.668 -3.519 -0.843 HD2A ATN 52 
ATN HA2  HA2  H 0 1 N N N 26.439 61.554 43.163 3.692  -0.867 1.499  HA2  ATN 53 
ATN HB21 1HB2 H 0 0 N N N 26.830 63.657 41.887 5.112  -1.505 -1.145 HB21 ATN 54 
ATN HB22 2HB2 H 0 0 N N N 26.591 62.862 40.364 5.827  -1.324 0.492  HB22 ATN 55 
ATN HG21 1HG2 H 0 0 N N N 28.975 62.458 42.268 5.252  -3.812 -0.457 HG21 ATN 56 
ATN HG22 2HG2 H 0 0 N N N 29.014 62.968 40.614 4.897  -3.410 1.255  HG22 ATN 57 
ATN HD31 1HD3 H 0 0 N N N 28.324 60.806 39.748 3.010  -3.677 -1.078 HD31 ATN 58 
ATN HD32 2HD3 H 0 0 N N N 29.279 60.336 41.124 2.707  -3.962 0.658  HD32 ATN 59 
ATN HN3  HN3  H 0 1 N N N 24.545 61.187 43.774 4.395  1.414  1.134  HN3  ATN 60 
ATN HA3  HA3  H 0 1 N N N 22.398 60.909 41.722 3.780  2.596  -1.464 HA3  ATN 61 
ATN HB31 1HB3 H 0 0 N N N 21.204 60.249 44.071 2.201  4.255  -0.513 HB31 ATN 62 
ATN HB32 2HB3 H 0 0 N N N 22.900 59.777 44.428 1.575  2.599  -0.329 HB32 ATN 63 
ATN HB33 3HB3 H 0 0 N N N 22.052 59.076 43.008 2.294  3.439  1.066  HB33 ATN 64 
ATN HN41 1HN4 H 0 0 N N N 21.355 63.395 44.909 4.134  5.239  -1.076 HN41 ATN 65 
ATN HN42 2HN4 H 0 0 N N N 22.056 61.766 44.990 5.501  5.581  -0.161 HN42 ATN 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 
ATN O1  C1   SING N N 1  
ATN O1  HO1  SING N N 2  
ATN C1  C    SING N N 3  
ATN C1  CA   SING N N 4  
ATN C1  HC1  SING N N 5  
ATN CB  CG   SING N N 6  
ATN CB  CA   SING N N 7  
ATN CB  HB1  SING N N 8  
ATN CB  HB2  SING N N 9  
ATN CG  CD1  DOUB Y N 10 
ATN CG  CD2  SING Y N 11 
ATN CD1 CE1  SING Y N 12 
ATN CD1 HD1  SING N N 13 
ATN CD2 CE2  DOUB Y N 14 
ATN CD2 HD2  SING N N 15 
ATN CE1 CZ   DOUB Y N 16 
ATN CE1 HE1  SING N N 17 
ATN CE2 CZ   SING Y N 18 
ATN CE2 HE2  SING N N 19 
ATN CZ  HZ   SING N N 20 
ATN C   O    DOUB N N 21 
ATN C   N1   SING N N 22 
ATN N   CA   SING N N 23 
ATN N   HN1  SING N N 24 
ATN N   HN2  SING N N 25 
ATN CA  HA   SING N N 26 
ATN N1  CA1  SING N N 27 
ATN N1  CD   SING N N 28 
ATN CA1 C2   SING N N 29 
ATN CA1 CB1  SING N N 30 
ATN CA1 HA1  SING N N 31 
ATN C2  O2   DOUB N N 32 
ATN C2  N2   SING N N 33 
ATN CB1 CG1  SING N N 34 
ATN CB1 HB11 SING N N 35 
ATN CB1 HB12 SING N N 36 
ATN CG1 CD   SING N N 37 
ATN CG1 HG11 SING N N 38 
ATN CG1 HG12 SING N N 39 
ATN CD  HD1A SING N N 40 
ATN CD  HD2A SING N N 41 
ATN N2  CA2  SING N N 42 
ATN N2  CD3  SING N N 43 
ATN CA2 C3   SING N N 44 
ATN CA2 CB2  SING N N 45 
ATN CA2 HA2  SING N N 46 
ATN C3  O3   DOUB N N 47 
ATN C3  N3   SING N N 48 
ATN CB2 CG2  SING N N 49 
ATN CB2 HB21 SING N N 50 
ATN CB2 HB22 SING N N 51 
ATN CG2 CD3  SING N N 52 
ATN CG2 HG21 SING N N 53 
ATN CG2 HG22 SING N N 54 
ATN CD3 HD31 SING N N 55 
ATN CD3 HD32 SING N N 56 
ATN N3  CA3  SING N N 57 
ATN N3  HN3  SING N N 58 
ATN CA3 C4   SING N N 59 
ATN CA3 CB3  SING N N 60 
ATN CA3 HA3  SING N N 61 
ATN C4  O4   DOUB N N 62 
ATN C4  N4   SING N N 63 
ATN CB3 HB31 SING N N 64 
ATN CB3 HB32 SING N N 65 
ATN CB3 HB33 SING N N 66 
ATN N4  HN41 SING N N 67 
ATN N4  HN42 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 
ATN SMILES           ACDLabs              10.04 O=C(N1C(C(=O)NC(C(=O)N)C)CCC1)C3N(C(=O)C(O)C(N)Cc2ccccc2)CCC3 
ATN InChI            InChI                1.02b 
InChI=1/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)/t14-,16+,17-,18-,19-/m0/s1/f/h26H,25H2 
ATN InChIKey         InChI                1.02b YVUUZAPYLPWFHE-BTHQMPKUDP 
ATN SMILES_CANONICAL CACTVS               3.341 C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)[C@@H](O)[C@H](N)Cc3ccccc3)C(N)=O 
ATN SMILES           CACTVS               3.341 C[CH](NC(=O)[CH]1CCCN1C(=O)[CH]2CCCN2C(=O)[CH](O)[CH](N)Cc3ccccc3)C(N)=O 
ATN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](Cc3ccccc3)N)O 
ATN SMILES           "OpenEye OEToolkits" 1.5.0 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 
ATN "SYSTEMATIC NAME" ACDLabs              10.04 1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-prolyl-L-prolyl-L-alaninamide                                                                   
ATN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]pyrrolidin-2-yl]carbonyl-N-[(2S)-1-amino-1-oxo-propan-2-yl]pyrrolidine-2-carboxamide 
# 
