data_588
# 
_chem_comp.id                                    588 
_chem_comp.name                                  "2-{[2-(2-CARBAMOYL-VINYL)-4-(2-METHANESULFONYLAMINO-2-PENTYLCARBAMOYL-ETHYL)-PHENYL]-OXALYL-AMINO}-BENZOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H32 N4 O9 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "COMPOUND 17" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-03-17 
_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                        588.629 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     588 
_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        1ONY 
_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 
588 O6   O6   O 0 1 N N N 35.671 29.820 23.144 -1.836 -0.703 -3.885 O6   588 1  
588 C24  C24  C 0 1 N N N 34.759 29.181 23.579 -1.700 -0.638 -2.547 C24  588 2  
588 O7   O7   O 0 1 N N N 33.956 29.686 24.549 -0.709 -0.134 -2.063 O7   588 3  
588 C8   C8   C 0 1 N N N 34.417 27.753 23.040 -2.768 -1.185 -1.661 C8   588 4  
588 O5   O5   O 0 1 N N N 34.591 26.800 23.810 -3.760 -1.689 -2.146 O5   588 5  
588 N4   N4   N 0 1 N N N 33.938 27.567 21.721 -2.632 -1.120 -0.322 N4   588 6  
588 C2   C2   C 0 1 Y N N 33.433 28.684 21.024 -1.493 -0.542 0.235  C2   588 7  
588 C3   C3   C 0 1 Y N N 32.094 29.088 21.337 -0.434 -1.340 0.643  C3   588 8  
588 C4   C4   C 0 1 Y N N 31.490 30.177 20.705 0.694  -0.765 1.195  C4   588 9  
588 C5   C5   C 0 1 Y N N 32.192 30.917 19.728 0.779  0.610  1.346  C5   588 10 
588 C6   C6   C 0 1 Y N N 33.526 30.544 19.404 -0.264 1.419  0.952  C6   588 11 
588 C1   C1   C 0 1 Y N N 34.172 29.438 20.035 -1.411 0.853  0.387  C1   588 12 
588 C17  C17  C 0 1 N N N 35.599 29.099 19.650 -2.525 1.710  -0.041 C17  588 13 
588 C18  C18  C 0 1 N N N 35.782 28.440 18.281 -2.402 3.053  0.011  C18  588 14 
588 C19  C19  C 0 1 N N N 37.290 28.382 17.945 -3.550 3.906  -0.298 C19  588 15 
588 O1   O1   O 0 1 N N N 37.749 28.972 16.983 -4.639 3.406  -0.511 O1   588 16 
588 N3   N3   N 0 1 N N N 38.036 27.641 18.782 -3.401 5.244  -0.348 N3   588 17 
588 C7   C7   C 0 1 N N N 31.512 32.076 19.038 2.016  1.222  1.950  C7   588 18 
588 C9   C9   C 0 1 N N S 30.993 31.742 17.598 2.970  1.651  0.833  C9   588 19 
588 N1   N1   N 0 1 N N N 30.371 32.935 17.034 2.305  2.632  -0.028 N1   588 20 
588 S1   S1   S 0 1 N N N 30.478 33.211 15.314 2.528  4.252  0.237  S1   588 21 
588 O4   O4   O 0 1 N N N 29.382 32.467 14.782 2.189  4.396  1.609  O4   588 22 
588 O2   O2   O 0 1 N N N 31.811 32.800 14.972 1.757  4.849  -0.797 O2   588 23 
588 C20  C20  C 0 1 N N N 30.297 34.947 15.004 4.306  4.475  -0.040 C20  588 24 
588 C11  C11  C 0 1 N N N 30.007 30.540 17.600 3.359  0.447  0.015  C11  588 25 
588 O8   O8   O 0 1 N N N 30.406 29.381 17.527 2.813  0.232  -1.047 O8   588 26 
588 N2   N2   N 0 1 N N N 28.705 30.901 17.704 4.314  -0.393 0.462  N2   588 27 
588 C12  C12  C 0 1 N N N 27.617 29.915 17.734 4.692  -1.564 -0.333 C12  588 28 
588 C13  C13  C 0 1 N N N 26.496 30.405 18.660 5.788  -2.343 0.395  C13  588 29 
588 C15  C15  C 0 1 N N N 26.905 30.372 20.142 6.183  -3.565 -0.435 C15  588 30 
588 C14  C14  C 0 1 N N N 26.210 31.458 20.963 7.280  -4.345 0.293  C14  588 31 
588 C16  C16  C 0 1 N N N 26.002 31.042 22.423 7.674  -5.567 -0.537 C16  588 32 
588 C26  C26  C 0 1 Y N N 33.916 26.260 21.086 -3.629 -1.631 0.505  C26  588 33 
588 C27  C27  C 0 1 Y N N 32.672 25.832 20.464 -4.585 -0.784 1.051  C27  588 34 
588 C28  C28  C 0 1 Y N N 32.523 24.592 19.816 -5.572 -1.293 1.871  C28  588 35 
588 C29  C29  C 0 1 Y N N 33.605 23.700 19.752 -5.618 -2.648 2.156  C29  588 36 
588 C30  C30  C 0 1 Y N N 34.837 24.055 20.335 -4.678 -3.504 1.624  C30  588 37 
588 C25  C25  C 0 1 Y N N 35.035 25.302 21.003 -3.676 -3.005 0.788  C25  588 38 
588 C31  C31  C 0 1 N N N 36.407 25.507 21.562 -2.667 -3.915 0.215  C31  588 39 
588 O9   O9   O 0 1 N N N 36.911 24.606 22.186 -1.864 -3.498 -0.596 O9   588 40 
588 O10  O10  O 0 1 N N N 37.049 26.537 21.453 -2.635 -5.208 0.592  O10  588 41 
588 HO6  HO6  H 0 1 N N N 36.233 29.466 22.465 -1.144 -0.348 -4.459 HO6  588 42 
588 H3   H3   H 0 1 N N N 31.506 28.540 22.093 -0.491 -2.413 0.529  H3   588 43 
588 H4   H4   H 0 1 N N N 30.458 30.453 20.978 1.516  -1.391 1.510  H4   588 44 
588 H6   H6   H 0 1 N N N 34.073 31.127 18.644 -0.193 2.490  1.073  H6   588 45 
588 H17  H17  H 0 1 N N N 36.447 29.317 20.321 -3.443 1.265  -0.397 H17  588 46 
588 H18  H18  H 0 1 N N N 34.963 28.069 17.643 -1.456 3.499  0.282  H18  588 47 
588 HN31 1HN3 H 0 0 N N N 39.031 27.603 18.560 -2.533 5.642  -0.178 HN31 588 48 
588 HN32 2HN3 H 0 0 N N N 37.652 27.147 19.587 -4.162 5.809  -0.554 HN32 588 49 
588 H71  1H7  H 0 1 N N N 32.182 32.967 19.016 2.510  0.490  2.588  H71  588 50 
588 H72  2H7  H 0 1 N N N 30.685 32.478 19.669 1.738  2.093  2.544  H72  588 51 
588 H9   H9   H 0 1 N N N 31.858 31.436 16.965 3.864  2.097  1.269  H9   588 52 
588 HN1  HN1  H 0 1 N N N 30.731 33.755 17.522 1.734  2.333  -0.753 HN1  588 53 
588 H201 1H20 H 0 0 N N N 31.027 35.562 15.581 4.555  4.181  -1.060 H201 588 54 
588 H202 2H20 H 0 0 N N N 30.365 35.123 13.905 4.568  5.522  0.110  H202 588 55 
588 H203 3H20 H 0 0 N N N 29.362 35.364 15.445 4.864  3.857  0.663  H203 588 56 
588 HN2  HN2  H 0 1 N N N 28.545 31.907 17.759 4.751  -0.221 1.311  HN2  588 57 
588 H121 1H12 H 0 0 N N N 27.980 28.899 18.016 5.062  -1.238 -1.305 H121 588 58 
588 H122 2H12 H 0 0 N N N 27.241 29.674 16.712 3.821  -2.205 -0.472 H122 588 59 
588 H131 1H13 H 0 0 N N N 25.555 29.832 18.490 5.418  -2.668 1.368  H131 588 60 
588 H132 2H13 H 0 0 N N N 26.144 31.420 18.363 6.659  -1.701 0.534  H132 588 61 
588 H151 1H15 H 0 0 N N N 28.013 30.430 20.255 6.553  -3.240 -1.408 H151 588 62 
588 H152 2H15 H 0 0 N N N 26.734 29.363 20.584 5.313  -4.207 -0.574 H152 588 63 
588 H141 1H14 H 0 0 N N N 25.247 31.765 20.491 6.910  -4.670 1.266  H141 588 64 
588 H142 2H14 H 0 0 N N N 26.758 32.426 20.895 8.150  -3.703 0.432  H142 588 65 
588 H161 1H16 H 0 0 N N N 26.965 30.735 22.895 8.456  -6.122 -0.018 H161 588 66 
588 H162 2H16 H 0 0 N N N 25.495 31.834 23.022 6.804  -6.209 -0.676 H162 588 67 
588 H163 3H16 H 0 0 N N N 25.454 30.074 22.491 8.045  -5.242 -1.510 H163 588 68 
588 H27  H27  H 0 1 N N N 31.786 26.489 20.485 -4.556 0.273  0.834  H27  588 69 
588 H28  H28  H 0 1 N N N 31.558 24.319 19.358 -6.313 -0.630 2.293  H28  588 70 
588 H29  H29  H 0 1 N N N 33.488 22.727 19.247 -6.395 -3.036 2.798  H29  588 71 
588 H30  H30  H 0 1 N N N 35.671 23.336 20.267 -4.718 -4.559 1.850  H30  588 72 
588 H10  H10  H 0 1 N N N 37.921 26.667 21.808 -1.929 -5.787 0.273  H10  588 73 
# 
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 
588 O6  C24  SING N N 1  
588 O6  HO6  SING N N 2  
588 C24 O7   DOUB N N 3  
588 C24 C8   SING N N 4  
588 C8  O5   DOUB N N 5  
588 C8  N4   SING N N 6  
588 N4  C2   SING N N 7  
588 N4  C26  SING N N 8  
588 C2  C3   DOUB Y N 9  
588 C2  C1   SING Y N 10 
588 C3  C4   SING Y N 11 
588 C3  H3   SING N N 12 
588 C4  C5   DOUB Y N 13 
588 C4  H4   SING N N 14 
588 C5  C6   SING Y N 15 
588 C5  C7   SING N N 16 
588 C6  C1   DOUB Y N 17 
588 C6  H6   SING N N 18 
588 C1  C17  SING N N 19 
588 C17 C18  DOUB N E 20 
588 C17 H17  SING N N 21 
588 C18 C19  SING N N 22 
588 C18 H18  SING N N 23 
588 C19 O1   DOUB N N 24 
588 C19 N3   SING N N 25 
588 N3  HN31 SING N N 26 
588 N3  HN32 SING N N 27 
588 C7  C9   SING N N 28 
588 C7  H71  SING N N 29 
588 C7  H72  SING N N 30 
588 C9  N1   SING N N 31 
588 C9  C11  SING N N 32 
588 C9  H9   SING N N 33 
588 N1  S1   SING N N 34 
588 N1  HN1  SING N N 35 
588 S1  O4   DOUB N N 36 
588 S1  O2   DOUB N N 37 
588 S1  C20  SING N N 38 
588 C20 H201 SING N N 39 
588 C20 H202 SING N N 40 
588 C20 H203 SING N N 41 
588 C11 O8   DOUB N N 42 
588 C11 N2   SING N N 43 
588 N2  C12  SING N N 44 
588 N2  HN2  SING N N 45 
588 C12 C13  SING N N 46 
588 C12 H121 SING N N 47 
588 C12 H122 SING N N 48 
588 C13 C15  SING N N 49 
588 C13 H131 SING N N 50 
588 C13 H132 SING N N 51 
588 C15 C14  SING N N 52 
588 C15 H151 SING N N 53 
588 C15 H152 SING N N 54 
588 C14 C16  SING N N 55 
588 C14 H141 SING N N 56 
588 C14 H142 SING N N 57 
588 C16 H161 SING N N 58 
588 C16 H162 SING N N 59 
588 C16 H163 SING N N 60 
588 C26 C27  DOUB Y N 61 
588 C26 C25  SING Y N 62 
588 C27 C28  SING Y N 63 
588 C27 H27  SING N N 64 
588 C28 C29  DOUB Y N 65 
588 C28 H28  SING N N 66 
588 C29 C30  SING Y N 67 
588 C29 H29  SING N N 68 
588 C30 C25  DOUB Y N 69 
588 C30 H30  SING N N 70 
588 C25 C31  SING N N 71 
588 C31 O9   DOUB N N 72 
588 C31 O10  SING N N 73 
588 O10 H10  SING N N 74 
# 
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 
588 SMILES           ACDLabs              10.04 O=C(N(c1ccc(cc1\C=C\C(=O)N)CC(C(=O)NCCCCC)NS(=O)(=O)C)c2ccccc2C(=O)O)C(=O)O 
588 InChI            InChI                1.02b 
;InChI=1/C27H32N4O9S/c1-3-4-7-14-29-24(33)20(30-41(2,39)40)16-17-10-12-21(18(15-17)11-13-23(28)32)31(25(34)27(37)38)22-9-6-5-8-19(22)26(35)36/h5-6,8-13,15,20,30H,3-4,7,14,16H2,1-2H3,(H2,28,32)(H,29,33)(H,35,36)(H,37,38)/b13-11+/t20-/m0/s1/f/h29,35,37H,28H2
;
588 InChIKey         InChI                1.02b FSRCMOQVSVRBJH-GVAVYRFZDB 
588 SMILES_CANONICAL CACTVS               3.341 CCCCCNC(=O)[C@H](Cc1ccc(N(C(=O)C(O)=O)c2ccccc2C(O)=O)c(\C=C\C(N)=O)c1)N[S](C)(=O)=O 
588 SMILES           CACTVS               3.341 CCCCCNC(=O)[CH](Cc1ccc(N(C(=O)C(O)=O)c2ccccc2C(O)=O)c(C=CC(N)=O)c1)N[S](C)(=O)=O 
588 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCCNC(=O)[C@H](Cc1ccc(c(c1)\C=C\C(=O)N)N(c2ccccc2C(=O)O)C(=O)C(=O)O)NS(=O)(=O)C 
588 SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCNC(=O)C(Cc1ccc(c(c1)C=CC(=O)N)N(c2ccccc2C(=O)O)C(=O)C(=O)O)NS(=O)(=O)C 
# 
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 
588 "SYSTEMATIC NAME" ACDLabs              10.04 "2-[{2-[(1E)-3-amino-3-oxoprop-1-en-1-yl]-4-[(2S)-2-[(methylsulfonyl)amino]-3-oxo-3-(pentylamino)propyl]phenyl}(carboxycarbonyl)amino]benzoic acid" 
588 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[2-[(E)-3-amino-3-oxo-prop-1-enyl]-4-[(2S)-2-(methylsulfonylamino)-3-oxo-3-(pentylamino)propyl]phenyl]-(carboxycarbonyl)amino]benzoic acid"     
# 
