data_18W
# 
_chem_comp.id                                    18W 
_chem_comp.name                                  "3-[(5Z)-5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-methyl-1H-pyrrol-2-yl]methylidene}-4-(carboxymethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]propanoic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H22 N2 O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-11-08 
_chem_comp.pdbx_modified_date                    2013-02-22 
_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                        434.397 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     18W 
_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        4HTG 
_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 
18W O3A O3A O 0 1 N N N -25.649 -6.172  30.917 -3.694 3.953  0.121  O3A 18W 1  
18W C9A C9A C 0 1 N N N -26.710 -6.837  30.848 -3.377 3.526  1.205  C9A 18W 2  
18W O4A O4A O 0 1 N N N -27.450 -7.100  31.828 -3.378 4.338  2.274  O4A 18W 3  
18W C8A C8A C 0 1 N N N -27.192 -7.176  29.413 -2.985 2.078  1.359  C8A 18W 4  
18W C7A C7A C 0 1 N N N -27.800 -8.544  29.412 -3.074 1.379  0.001  C7A 18W 5  
18W C3A C3A C 0 1 Y N N -28.257 -8.970  27.928 -2.682 -0.068 0.155  C3A 18W 6  
18W C2A C2A C 0 1 Y N N -27.477 -9.686  27.016 -3.537 -1.133 0.448  C2A 18W 7  
18W C5A C5A C 0 1 N N N -26.032 -10.184 27.237 -5.025 -1.040 0.667  C5A 18W 8  
18W C6A C6A C 0 1 N N N -24.884 -9.219  26.808 -5.739 -1.215 -0.648 C6A 18W 9  
18W O2A O2A O 0 1 N N N -23.725 -9.600  27.052 -7.080 -1.169 -0.696 O2A 18W 10 
18W O1A O1A O 0 1 N N N -25.131 -8.169  26.212 -5.105 -1.397 -1.660 O1A 18W 11 
18W C1A C1A C 0 1 Y N N -28.229 -9.866  25.900 -2.793 -2.265 0.500  C1A 18W 12 
18W CHA CHA C 0 1 N N N -27.876 -10.608 24.660 -3.319 -3.646 0.794  CHA 18W 13 
18W NA  NA  N 0 1 Y N N -29.389 -9.273  26.169 -1.496 -1.952 0.250  NA  18W 14 
18W C4A C4A C 0 1 Y N N -29.456 -8.737  27.404 -1.406 -0.595 0.027  C4A 18W 15 
18W CHB CHB C 0 1 N N N -30.571 -8.068  27.971 -0.231 0.127  -0.266 CHB 18W 16 
18W C1B C1B C 0 1 N N N -31.626 -7.391  27.328 1.005  -0.433 -0.012 C1B 18W 17 
18W C2B C2B C 0 1 N N N -32.421 -6.410  27.836 2.254  0.102  -0.382 C2B 18W 18 
18W C5B C5B C 0 1 N N N -32.362 -5.883  29.306 2.487  1.391  -1.128 C5B 18W 19 
18W C6B C6B C 0 1 N N N -33.090 -6.817  30.333 2.379  1.139  -2.610 C6B 18W 20 
18W O2B O2B O 0 1 N N N -34.070 -7.488  29.934 2.138  0.028  -3.018 O2B 18W 21 
18W O1B O1B O 0 1 N N N -32.607 -6.921  31.506 2.550  2.150  -3.477 O1B 18W 22 
18W NB  NB  N 0 1 N N N -32.066 -7.583  26.001 1.244  -1.628 0.663  NB  18W 23 
18W C4B C4B C 0 1 N N N -33.097 -6.763  25.715 2.575  -1.827 0.712  C4B 18W 24 
18W O5B O5B O 0 1 N N N -33.782 -6.691  24.594 3.134  -2.779 1.232  O5B 18W 25 
18W C3B C3B C 0 1 N N N -33.319 -6.043  26.838 3.214  -0.758 0.059  C3B 18W 26 
18W C7B C7B C 0 1 N N N -34.369 -4.915  26.952 4.701  -0.589 -0.114 C7B 18W 27 
18W C8B C8B C 0 1 N N N -33.704 -3.551  26.524 5.287  0.081  1.130  C8B 18W 28 
18W C9B C9B C 0 1 N N N -34.700 -2.444  26.308 6.775  0.250  0.956  C9B 18W 29 
18W O4B O4B O 0 1 N N N -34.529 -1.354  26.897 7.504  0.819  1.929  O4B 18W 30 
18W O3B O3B O 0 1 N N N -35.583 -2.669  25.402 7.311  -0.127 -0.059 O3B 18W 31 
18W H1  H1  H 0 1 N N N -27.080 -6.719  32.616 -3.641 5.257  2.126  H1  18W 32 
18W H2  H2  H 0 1 N N N -26.337 -7.152  28.722 -1.964 2.016  1.734  H2  18W 33 
18W H3  H3  H 0 1 N N N -27.943 -6.439  29.093 -3.661 1.592  2.063  H3  18W 34 
18W H4  H4  H 0 1 N N N -28.678 -8.548  30.074 -4.096 1.441  -0.373 H4  18W 35 
18W H5  H5  H 0 1 N N N -27.059 -9.268  29.782 -2.398 1.865  -0.703 H5  18W 36 
18W H6  H6  H 0 1 N N N -25.911 -11.118 26.669 -5.340 -1.821 1.359  H6  18W 37 
18W H7  H7  H 0 1 N N N -25.911 -10.389 28.311 -5.271 -0.064 1.086  H7  18W 38 
18W H8  H8  H 0 1 N N N -23.105 -8.966  26.712 -7.493 -1.288 -1.562 H8  18W 39 
18W H9  H9  H 0 1 N N N -27.416 -9.918  23.937 -3.290 -3.825 1.868  H9  18W 40 
18W H10 H10 H 0 1 N N N -27.165 -11.411 24.903 -4.347 -3.726 0.440  H10 18W 41 
18W H11 H11 H 0 1 N N N -28.786 -11.044 24.222 -2.701 -4.387 0.285  H11 18W 42 
18W H12 H12 H 0 1 N N N -30.143 -9.229  25.514 -0.756 -2.580 0.227  H12 18W 43 
18W H13 H13 H 0 1 N N N -30.618 -8.079  29.050 -0.297 1.117  -0.691 H13 18W 44 
18W H15 H15 H 0 1 N N N -31.306 -5.795  29.603 1.738  2.124  -0.829 H15 18W 45 
18W H16 H16 H 0 1 N N N -32.836 -4.891  29.340 3.481  1.772  -0.895 H16 18W 46 
18W H17 H17 H 0 1 N N N -33.101 -7.567  31.996 2.471  1.940  -4.417 H17 18W 47 
18W H18 H18 H 0 1 N N N -34.722 -4.843  27.991 5.164  -1.566 -0.253 H18 18W 48 
18W H19 H19 H 0 1 N N N -35.220 -5.134  26.290 4.897  0.033  -0.988 H19 18W 49 
18W H20 H20 H 0 1 N N N -33.152 -3.711  25.586 4.825  1.058  1.268  H20 18W 50 
18W H21 H21 H 0 1 N N N -33.004 -3.241  27.314 5.092  -0.540 2.004  H21 18W 51 
18W H22 H22 H 0 1 N N N -35.153 -0.716  26.571 8.454  0.906  1.772  H22 18W 52 
18W H14 H14 H 0 1 N N N -31.667 -8.238  25.360 0.568  -2.215 1.035  H14 18W 53 
# 
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 
18W O5B C4B DOUB N N 1  
18W CHA C1A SING N N 2  
18W O3B C9B DOUB N N 3  
18W C4B NB  SING N N 4  
18W C4B C3B SING N N 5  
18W C1A NA  SING Y N 6  
18W C1A C2A DOUB Y N 7  
18W NB  C1B SING N N 8  
18W NA  C4A SING Y N 9  
18W O1A C6A DOUB N N 10 
18W C9B C8B SING N N 11 
18W C9B O4B SING N N 12 
18W C8B C7B SING N N 13 
18W C6A O2A SING N N 14 
18W C6A C5A SING N N 15 
18W C3B C7B SING N N 16 
18W C3B C2B DOUB N N 17 
18W C2A C5A SING N N 18 
18W C2A C3A SING Y N 19 
18W C1B C2B SING N N 20 
18W C1B CHB DOUB N Z 21 
18W C4A C3A DOUB Y N 22 
18W C4A CHB SING N N 23 
18W C2B C5B SING N N 24 
18W C3A C7A SING N N 25 
18W C5B C6B SING N N 26 
18W C7A C8A SING N N 27 
18W C8A C9A SING N N 28 
18W O2B C6B DOUB N N 29 
18W C6B O1B SING N N 30 
18W C9A O3A DOUB N N 31 
18W C9A O4A SING N N 32 
18W O4A H1  SING N N 33 
18W C8A H2  SING N N 34 
18W C8A H3  SING N N 35 
18W C7A H4  SING N N 36 
18W C7A H5  SING N N 37 
18W C5A H6  SING N N 38 
18W C5A H7  SING N N 39 
18W O2A H8  SING N N 40 
18W CHA H9  SING N N 41 
18W CHA H10 SING N N 42 
18W CHA H11 SING N N 43 
18W NA  H12 SING N N 44 
18W CHB H13 SING N N 45 
18W C5B H15 SING N N 46 
18W C5B H16 SING N N 47 
18W O1B H17 SING N N 48 
18W C7B H18 SING N N 49 
18W C7B H19 SING N N 50 
18W C8B H20 SING N N 51 
18W C8B H21 SING N N 52 
18W O4B H22 SING N N 53 
18W NB  H14 SING N N 54 
# 
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 
18W SMILES           ACDLabs              12.01 "O=C2C(=C(\C(=C\c1c(c(c(n1)C)CC(=O)O)CCC(=O)O)N2)CC(=O)O)CCC(=O)O"                                                                                                                    
18W InChI            InChI                1.03  "InChI=1S/C20H22N2O9/c1-9-12(6-18(27)28)10(2-4-16(23)24)14(21-9)8-15-13(7-19(29)30)11(20(31)22-15)3-5-17(25)26/h8,21H,2-7H2,1H3,(H,22,31)(H,23,24)(H,25,26)(H,27,28)(H,29,30)/b15-8-" 
18W InChIKey         InChI                1.03  MBSNQHZDABRTAT-NVNXTCNLSA-N                                                                                                                                                           
18W SMILES_CANONICAL CACTVS               3.370 "Cc1[nH]c(/C=C/2NC(=O)C(=C/2CC(O)=O)CCC(O)=O)c(CCC(O)=O)c1CC(O)=O"                                                                                                                    
18W SMILES           CACTVS               3.370 "Cc1[nH]c(C=C2NC(=O)C(=C2CC(O)=O)CCC(O)=O)c(CCC(O)=O)c1CC(O)=O"                                                                                                                       
18W SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1c(c(c([nH]1)/C=C\2/C(=C(C(=O)N2)CCC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)O"                                                                                                                
18W SMILES           "OpenEye OEToolkits" 1.7.6 "Cc1c(c(c([nH]1)C=C2C(=C(C(=O)N2)CCC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)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 
18W "SYSTEMATIC NAME" ACDLabs              12.01 "3-[(5Z)-5-{[3-(2-carboxyethyl)-4-(carboxymethyl)-5-methyl-1H-pyrrol-2-yl]methylidene}-4-(carboxymethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]propanoic acid"                
18W "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "3-[4-(2-hydroxy-2-oxoethyl)-2-[(Z)-[3-(2-hydroxy-2-oxoethyl)-4-(3-hydroxy-3-oxopropyl)-5-oxidanylidene-pyrrol-2-ylidene]methyl]-5-methyl-1H-pyrrol-3-yl]propanoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
18W "Create component" 2012-11-08 RCSB 
18W "Initial release"  2013-02-22 RCSB 
# 
