data_COE
# 
_chem_comp.id                                    COE 
_chem_comp.name                                  "FURO[2,3D]PYRIMIDINE ANTIFOLATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H22 N6 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   OBS 
_chem_comp.pdbx_replaced_by                      MOT 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        442.425 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     COE 
_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        1DAJ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
COE N1   N1   N 0 1 Y N N 11.425 2.333  11.749 -1.105 1.790  5.979  N1   COE 1  
COE C2   C2   C 0 1 Y N N 10.370 2.389  12.570 -2.103 1.074  6.470  C2   COE 2  
COE NA2  NA2  N 0 1 N N N 9.437  1.478  12.356 -2.971 1.670  7.369  NA2  COE 3  
COE N3   N3   N 0 1 Y N N 10.245 3.244  13.525 -2.304 -0.193 6.134  N3   COE 4  
COE C4   C4   C 0 1 Y N N 11.129 4.121  13.811 -1.496 -0.807 5.275  C4   COE 5  
COE N4   N4   N 0 1 N N N 10.949 4.982  14.815 -1.706 -2.129 4.926  N4   COE 6  
COE C4A  C4A  C 0 1 Y N N 12.214 4.126  13.034 -0.430 -0.081 4.726  C4A  COE 7  
COE C6   C6   C 0 1 Y N N 13.434 4.919  12.941 0.655  -0.372 3.786  C6   COE 8  
COE C7   C7   C 0 1 Y N N 14.049 4.327  11.912 1.365  0.759  3.677  C7   COE 9  
COE O8   O8   O 0 1 Y N N 13.400 3.399  11.415 0.831  1.716  4.459  O8   COE 10 
COE C8A  C8A  C 0 1 Y N N 12.352 3.255  12.041 -0.248 1.257  5.112  C8A  COE 11 
COE C9   C9   C 0 1 N N N 13.794 6.061  13.832 0.916  -1.678 3.081  C9   COE 12 
COE N10  N10  N 0 1 N N N 14.855 7.027  13.487 2.097  -1.542 2.224  N10  COE 13 
COE C10  C10  C 0 1 N N N 16.159 6.748  14.133 3.427  -1.846 2.758  C10  COE 14 
COE C11  C11  C 0 1 Y N N 14.832 8.764  9.783  1.674  -0.293 -1.722 C11  COE 15 
COE C12  C12  C 0 1 Y N N 13.671 8.418  10.394 2.942  -0.583 -1.211 C12  COE 16 
COE C13  C13  C 0 1 Y N N 13.666 7.877  11.618 3.079  -0.996 0.093  C13  COE 17 
COE C14  C14  C 0 1 Y N N 14.799 7.614  12.288 1.956  -1.125 0.906  C14  COE 18 
COE C15  C15  C 0 1 Y N N 15.946 7.938  11.664 0.690  -0.842 0.399  C15  COE 19 
COE C16  C16  C 0 1 Y N N 15.977 8.498  10.444 0.548  -0.423 -0.904 C16  COE 20 
COE C    C    C 0 1 N N N 14.805 9.308  8.555  1.523  0.149  -3.121 C    COE 21 
COE O    O    O 0 1 N N N 15.731 9.924  8.056  2.504  0.262  -3.831 O    COE 22 
COE N    N    N 0 1 N N N 13.702 9.198  7.769  0.300  0.429  -3.612 N    COE 23 
COE CA   CA   C 0 1 N N S 13.783 10.282 6.730  0.151  0.869  -5.001 CA   COE 24 
COE CB   CB   C 0 1 N N N 14.822 9.853  5.676  -1.209 0.419  -5.535 CB   COE 25 
COE CG   CG   C 0 1 N N N 14.321 9.553  4.258  -1.303 -1.106 -5.471 CG   COE 26 
COE CD   CD   C 0 1 N N N 14.909 8.286  3.691  -2.644 -1.550 -5.997 CD   COE 27 
COE OE1  OE1  O 0 1 N N N 15.903 7.791  4.207  -3.442 -0.730 -6.384 OE1  COE 28 
COE OE2  OE2  O 0 1 N N N 14.363 7.766  2.731  -2.951 -2.856 -6.036 OE2  COE 29 
COE CT   CT   C 0 1 N N N 12.392 10.577 6.252  0.243  2.372  -5.064 CT   COE 30 
COE O1   O1   O 0 1 N N N 11.427 9.869  6.542  0.680  2.909  -6.054 O1   COE 31 
COE O2   O2   O 0 1 N N N 12.144 11.587 5.601  -0.160 3.114  -4.021 O2   COE 32 
COE HN21 1HN2 H 0 0 N N N 8.632  1.520  12.981 -3.709 1.162  7.740  HN21 COE 33 
COE HN22 2HN2 H 0 0 N N N 9.847  0.544  12.377 -2.842 2.596  7.627  HN22 COE 34 
COE HN41 1HN4 H 0 0 N N N 11.654 5.682  15.043 -2.450 -2.619 5.309  HN41 COE 35 
COE HN42 2HN4 H 0 0 N N N 10.752 4.445  15.659 -1.110 -2.565 4.298  HN42 COE 36 
COE H7   H7   H 0 1 N N N 15.036 4.589  11.496 2.238  0.884  3.054  H7   COE 37 
COE H91  1H9  H 0 1 N N N 12.862 6.639  14.032 0.052  -1.939 2.469  H91  COE 38 
COE H92  2H9  H 0 1 N N N 14.032 5.642  14.837 1.090  -2.461 3.818  H92  COE 39 
COE H101 1H10 H 0 0 N N N 16.960 7.477  13.872 3.339  -2.154 3.799  H101 COE 40 
COE H102 2H10 H 0 0 N N N 16.040 6.676  15.239 3.876  -2.652 2.177  H102 COE 41 
COE H103 3H10 H 0 0 N N N 16.490 5.706  13.911 4.056  -0.958 2.694  H103 COE 42 
COE H12  H12  H 0 1 N N N 12.707 8.580  9.882  3.814  -0.484 -1.841 H12  COE 43 
COE H13  H13  H 0 1 N N N 12.697 7.640  12.089 4.059  -1.220 0.488  H13  COE 44 
COE H15  H15  H 0 1 N N N 16.902 7.735  12.174 -0.178 -0.942 1.031  H15  COE 45 
COE H16  H16  H 0 1 N N N 16.948 8.740  9.982  -0.433 -0.199 -1.295 H16  COE 46 
COE HN   HN   H 0 1 N N N 12.991 8.481  7.920  -0.481 0.339  -3.045 HN   COE 47 
COE HA   HA   H 0 1 N N N 14.157 11.261 7.110  0.943  0.430  -5.608 HA   COE 48 
COE HB1  1HB  H 0 1 N N N 15.630 10.619 5.624  -2.001 0.857  -4.928 HB1  COE 49 
COE HB2  2HB  H 0 1 N N N 15.389 8.972  6.058  -1.320 0.746  -6.569 HB2  COE 50 
COE HG1  1HG  H 0 1 N N N 13.206 9.527  4.223  -0.511 -1.545 -6.078 HG1  COE 51 
COE HG2  2HG  H 0 1 N N N 14.502 10.417 3.578  -1.192 -1.434 -4.437 HG2  COE 52 
COE HOE2 2HOE H 0 0 N N N 14.733 6.967  2.373  -3.811 -3.140 -6.374 HOE2 COE 53 
COE HO2  HO2  H 0 1 N N N 11.263 11.773 5.298  -0.100 4.078  -4.062 HO2  COE 54 
# 
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 
COE N1  C2   DOUB Y N 1  
COE N1  C8A  SING Y N 2  
COE C2  NA2  SING N N 3  
COE C2  N3   SING Y N 4  
COE NA2 HN21 SING N N 5  
COE NA2 HN22 SING N N 6  
COE N3  C4   DOUB Y N 7  
COE C4  N4   SING N N 8  
COE C4  C4A  SING Y N 9  
COE N4  HN41 SING N N 10 
COE N4  HN42 SING N N 11 
COE C4A C6   SING Y N 12 
COE C4A C8A  DOUB Y N 13 
COE C6  C7   DOUB Y N 14 
COE C6  C9   SING N N 15 
COE C7  O8   SING Y N 16 
COE C7  H7   SING N N 17 
COE O8  C8A  SING Y N 18 
COE C9  N10  SING N N 19 
COE C9  H91  SING N N 20 
COE C9  H92  SING N N 21 
COE N10 C10  SING N N 22 
COE N10 C14  SING N N 23 
COE C10 H101 SING N N 24 
COE C10 H102 SING N N 25 
COE C10 H103 SING N N 26 
COE C11 C12  DOUB Y N 27 
COE C11 C16  SING Y N 28 
COE C11 C    SING N N 29 
COE C12 C13  SING Y N 30 
COE C12 H12  SING N N 31 
COE C13 C14  DOUB Y N 32 
COE C13 H13  SING N N 33 
COE C14 C15  SING Y N 34 
COE C15 C16  DOUB Y N 35 
COE C15 H15  SING N N 36 
COE C16 H16  SING N N 37 
COE C   O    DOUB N N 38 
COE C   N    SING N N 39 
COE N   CA   SING N N 40 
COE N   HN   SING N N 41 
COE CA  CB   SING N N 42 
COE CA  CT   SING N N 43 
COE CA  HA   SING N N 44 
COE CB  CG   SING N N 45 
COE CB  HB1  SING N N 46 
COE CB  HB2  SING N N 47 
COE CG  CD   SING N N 48 
COE CG  HG1  SING N N 49 
COE CG  HG2  SING N N 50 
COE CD  OE1  DOUB N N 51 
COE CD  OE2  SING N N 52 
COE OE2 HOE2 SING N N 53 
COE CT  O1   DOUB N N 54 
COE CT  O2   SING N N 55 
COE O2  HO2  SING N N 56 
# 
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 
COE SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)N(C)Cc2c3c(nc(nc3oc2)N)N)CCC(=O)O 
COE InChI            InChI                1.02b 
InChI=1/C20H22N6O6/c1-26(8-11-9-32-18-15(11)16(21)24-20(22)25-18)12-4-2-10(3-5-12)17(29)23-13(19(30)31)6-7-14(27)28/h2-5,9,13H,6-8H2,1H3,(H,23,29)(H,27,28)(H,30,31)(H4,21,22,24,25)/t13-/m0/s1/f/h23,27,30H,21-22H2 
COE InChIKey         InChI                1.02b WXINNGCGSCFUCR-DUSIDQMFDW 
COE SMILES_CANONICAL CACTVS               3.341 CN(Cc1coc2nc(N)nc(N)c12)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O 
COE SMILES           CACTVS               3.341 CN(Cc1coc2nc(N)nc(N)c12)c3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O 
COE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[N@](Cc1coc2c1c(nc(n2)N)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
COE SMILES           "OpenEye OEToolkits" 1.5.0 CN(Cc1coc2c1c(nc(n2)N)N)c3ccc(cc3)C(=O)NC(CCC(=O)O)C(=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 
COE "SYSTEMATIC NAME" ACDLabs              10.04 "N-[(4-{[(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)methyl](methyl)amino}phenyl)carbonyl]-L-glutamic acid"          
COE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(2,4-diaminofuro[4,5-e]pyrimidin-5-yl)methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid" 
# 
