data_MT1
# 
_chem_comp.id                                    MT1 
_chem_comp.name                                  "N-(4-{[(2,4-DIAMINOPTERIDIN-1-IUM-6-YL)METHYL](METHYL)AMINO}BENZOYL)-L-GLUTAMIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 N8 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "METHOTREXATE PROTONATED AT N1" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2006-10-25 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        455.447 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MT1 
_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        ? 
_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 
MT1 N1   N1   N 1 1 Y N N 16.254 65.343 45.628 5.889  4.269  -7.413  N1   MT1 1  
MT1 C2   C2   C 0 1 Y N N 15.629 65.494 46.795 5.153  3.693  -8.367  C2   MT1 2  
MT1 NA2  NA2  N 0 1 N N N 14.472 65.049 47.021 5.793  2.671  -9.091  NA2  MT1 3  
MT1 N3   N3   N 0 1 Y N N 16.313 66.181 47.729 3.887  4.018  -8.664  N3   MT1 4  
MT1 C4   C4   C 0 1 Y N N 17.533 66.798 47.620 3.384  5.010  -7.901  C4   MT1 5  
MT1 NA4  NA4  N 0 1 N N N 18.137 67.466 48.588 2.046  5.410  -8.157  NA4  MT1 6  
MT1 C4A  C4A  C 0 1 Y N N 18.139 66.622 46.329 4.069  5.668  -6.890  C4A  MT1 7  
MT1 N5   N5   N 0 1 Y N N 19.316 67.222 46.110 3.496  6.650  -6.171  N5   MT1 8  
MT1 C6   C6   C 0 1 Y N N 19.900 67.060 44.906 4.245  7.220  -5.217  C6   MT1 9  
MT1 C7   C7   C 0 1 Y N N 19.269 66.303 43.996 5.532  6.842  -4.963  C7   MT1 10 
MT1 N8   N8   N 0 1 Y N N 18.117 65.740 44.179 6.123  5.862  -5.670  N8   MT1 11 
MT1 C8A  C8A  C 0 1 Y N N 17.539 65.947 45.414 5.394  5.263  -6.644  C8A  MT1 12 
MT1 C9   C9   C 0 1 N N N 21.243 67.772 44.749 3.609  8.318  -4.414  C9   MT1 13 
MT1 N10  N10  N 0 1 N N N 21.498 67.951 43.267 2.265  7.974  -3.995  N10  MT1 14 
MT1 CM   CM   C 0 1 N N N 22.681 67.298 42.801 1.155  8.790  -4.444  CM   MT1 15 
MT1 C11  C11  C 0 1 Y N N 19.076 70.072 40.641 1.603  4.702  -1.498  C11  MT1 16 
MT1 C12  C12  C 0 1 Y N N 20.212 69.427 40.197 0.550  5.199  -2.237  C12  MT1 17 
MT1 C13  C13  C 0 1 Y N N 20.993 68.723 41.092 0.771  6.294  -3.072  C13  MT1 18 
MT1 C14  C14  C 0 1 Y N N 20.656 68.686 42.432 2.041  6.866  -3.151  C14  MT1 19 
MT1 C15  C15  C 0 1 Y N N 19.522 69.389 42.865 3.089  6.344  -2.393  C15  MT1 20 
MT1 C16  C16  C 0 1 Y N N 18.751 70.042 42.022 2.868  5.250  -1.557  C16  MT1 21 
MT1 C    C    C 0 1 N N N 18.192 70.807 39.733 1.367  3.535  -0.609  C    MT1 22 
MT1 O    O    O 0 1 N N N 18.525 70.965 38.552 0.238  3.334  -0.169  O    MT1 23 
MT1 N    N    N 0 1 N N N 17.021 71.275 40.129 2.470  2.746  -0.368  N    MT1 24 
MT1 CA   CA   C 0 1 N N S 16.108 72.091 39.288 2.394  1.548  0.466   CA   MT1 25 
MT1 CT   CT   C 0 1 N N N 15.473 73.051 40.250 3.710  1.408  1.210   CT   MT1 26 
MT1 O1   O1   O 0 1 N N N 15.409 72.658 41.464 4.610  2.354  0.834   O1   MT1 27 
MT1 O2   O2   O 0 1 N N N 15.012 74.095 39.799 3.961  0.557  2.054   O2   MT1 28 
MT1 CB   CB   C 0 1 N N N 14.937 71.256 38.799 2.053  0.292  -0.352  CB   MT1 29 
MT1 CG   CG   C 0 1 N N N 15.267 70.222 37.612 3.111  -0.168 -1.359  CG   MT1 30 
MT1 CD   CD   C 0 1 N N N 15.609 70.913 36.229 3.366  0.819  -2.471  CD   MT1 31 
MT1 OE1  OE1  O 0 1 N N N 16.329 70.144 35.456 4.471  1.275  -2.740  OE1  MT1 32 
MT1 OE2  OE2  O 0 1 N N N 15.213 72.115 35.969 2.241  1.141  -3.155  OE2  MT1 33 
MT1 H    H    H 0 1 N N N 16.770 71.095 40.931 3.358  2.927  -0.809  H    MT1 34 
MT1 H1   H1   H 0 1 N N N 15.886 64.883 45.001 6.845  3.954  -7.259  H1   MT1 35 
MT1 HA21 1HA2 H 0 0 N N N 14.160 65.254 47.949 5.648  2.604  -10.080 HA21 MT1 36 
MT1 HA22 2HA2 H 0 0 N N N 13.927 64.548 46.349 6.310  1.968  -8.598  HA22 MT1 37 
MT1 HA41 1HA4 H 0 0 N N N 18.289 66.859 49.368 1.726  5.434  -9.099  HA41 MT1 38 
MT1 HA42 2HA4 H 0 0 N N N 19.016 67.810 48.257 1.495  5.746  -7.400  HA42 MT1 39 
MT1 H7   H7   H 0 1 N N N 19.756 66.152 43.044 6.140  7.300  -4.193  H7   MT1 40 
MT1 H91  1H9  H 0 1 N N N 22.045 67.169 45.200 4.198  8.529  -3.515  H91  MT1 41 
MT1 H92  2H9  H 0 1 N N N 21.223 68.748 45.256 3.553  9.246  -4.992  H92  MT1 42 
MT1 HM1  1HM  H 0 1 N N N 22.605 67.130 41.717 1.392  9.850  -4.318  HM1  MT1 43 
MT1 HM2  2HM  H 0 1 N N N 23.556 67.930 43.014 0.257  8.560  -3.864  HM2  MT1 44 
MT1 HM3  3HM  H 0 1 N N N 22.792 66.332 43.314 0.948  8.599  -5.501  HM3  MT1 45 
MT1 H12  H12  H 0 1 N N N 20.489 69.473 39.154 -0.443 4.761  -2.183  H12  MT1 46 
MT1 H13  H13  H 0 1 N N N 21.871 68.199 40.744 -0.052 6.694  -3.659  H13  MT1 47 
MT1 H15  H15  H 0 1 N N N 19.276 69.394 43.916 4.082  6.782  -2.447  H15  MT1 48 
MT1 H16  H16  H 0 1 N N N 17.871 70.555 42.381 3.692  4.851  -0.971  H16  MT1 49 
MT1 HA   HA   H 0 1 N N N 16.661 72.529 38.444 1.606  1.720  1.209   HA   MT1 50 
MT1 HO1  HO1  H 0 1 N N N 14.943 73.303 41.982 5.479  2.310  1.287   HO1  MT1 51 
MT1 HB1  1HB  H 0 1 N N N 14.169 71.950 38.428 1.096  0.451  -0.866  HB1  MT1 52 
MT1 HB2  2HB  H 0 1 N N N 14.621 70.644 39.657 1.885  -0.539 0.346   HB2  MT1 53 
MT1 HG1  1HG  H 0 1 N N N 14.384 69.584 37.463 4.064  -0.386 -0.864  HG1  MT1 54 
MT1 HG2  2HG  H 0 1 N N N 16.161 69.659 37.918 2.797  -1.110 -1.825  HG2  MT1 55 
MT1 HOE2 HOE2 H 0 0 N N N 15.527 72.373 35.110 2.368  1.774  -3.893  HOE2 MT1 56 
# 
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 
MT1 N1  H1   SING N N 1  
MT1 N1  C8A  DOUB Y N 2  
MT1 N1  C2   SING Y N 3  
MT1 C2  NA2  SING N N 4  
MT1 C2  N3   DOUB Y N 5  
MT1 NA2 HA21 SING N N 6  
MT1 NA2 HA22 SING N N 7  
MT1 N3  C4   SING Y N 8  
MT1 C4  C4A  DOUB Y N 9  
MT1 C4  NA4  SING N N 10 
MT1 NA4 HA41 SING N N 11 
MT1 NA4 HA42 SING N N 12 
MT1 C4A C8A  SING Y N 13 
MT1 C4A N5   SING Y N 14 
MT1 N5  C6   DOUB Y N 15 
MT1 C6  C7   SING Y N 16 
MT1 C6  C9   SING N N 17 
MT1 C7  N8   DOUB Y N 18 
MT1 C7  H7   SING N N 19 
MT1 N8  C8A  SING Y N 20 
MT1 C9  N10  SING N N 21 
MT1 C9  H91  SING N N 22 
MT1 C9  H92  SING N N 23 
MT1 N10 C14  SING N N 24 
MT1 N10 CM   SING N N 25 
MT1 CM  HM1  SING N N 26 
MT1 CM  HM2  SING N N 27 
MT1 CM  HM3  SING N N 28 
MT1 C11 C    SING N N 29 
MT1 C11 C12  DOUB Y N 30 
MT1 C11 C16  SING Y N 31 
MT1 C12 C13  SING Y N 32 
MT1 C12 H12  SING N N 33 
MT1 C13 C14  DOUB Y N 34 
MT1 C13 H13  SING N N 35 
MT1 C14 C15  SING Y N 36 
MT1 C15 C16  DOUB Y N 37 
MT1 C15 H15  SING N N 38 
MT1 C16 H16  SING N N 39 
MT1 C   O    DOUB N N 40 
MT1 C   N    SING N N 41 
MT1 N   CA   SING N N 42 
MT1 N   H    SING N N 43 
MT1 CA  CB   SING N N 44 
MT1 CA  CT   SING N N 45 
MT1 CA  HA   SING N N 46 
MT1 CT  O2   DOUB N N 47 
MT1 CT  O1   SING N N 48 
MT1 O1  HO1  SING N N 49 
MT1 CB  CG   SING N N 50 
MT1 CB  HB1  SING N N 51 
MT1 CB  HB2  SING N N 52 
MT1 CG  CD   SING N N 53 
MT1 CG  HG1  SING N N 54 
MT1 CG  HG2  SING N N 55 
MT1 CD  OE1  DOUB N N 56 
MT1 CD  OE2  SING N N 57 
MT1 OE2 HOE2 SING N N 58 
# 
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 
MT1 SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)N(C)Cc2nc3c(nc2)[nH+]c(nc3N)N)CCC(=O)O 
MT1 InChI            InChI                1.02b 
InChI=1/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/p+1/t13-/m0/s1/fC20H23N8O5/h25,27,29,32H,21-22H2/q+1 
MT1 InChIKey         InChI                1.02b FBOZXECLQNJBKD-GCIXHFMUDE 
MT1 SMILES_CANONICAL CACTVS               3.341 CN(Cc1cnc2[nH+]c(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O 
MT1 SMILES           CACTVS               3.341 CN(Cc1cnc2[nH+]c(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O 
MT1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(Cc1cnc2c(n1)c(nc([nH+]2)N)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
MT1 SMILES           "OpenEye OEToolkits" 1.5.0 CN(Cc1cnc2c(n1)c(nc([nH+]2)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 
MT1 "SYSTEMATIC NAME" ACDLabs              10.04 "N-[(4-{[(2,4-diaminopteridin-1-ium-6-yl)methyl](methyl)amino}phenyl)carbonyl]-L-glutamic acid"          
MT1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(2,4-diaminopteridin-1-ium-6-yl)methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid" 
# 
