data_CB3
# 
_chem_comp.id                                    CB3 
_chem_comp.name                                  "10-PROPARGYL-5,8-DIDEAZAFOLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H23 N5 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                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        477.469 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CB3 
_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        1KCE 
_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 
CB3 N1   N1   N 0 1 Y N N 48.317 34.654 23.143 1.982  0.677  -6.203 N1   CB3 1  
CB3 C2   C2   C 0 1 Y N N 48.608 34.964 24.419 3.113  -0.034 -5.955 C2   CB3 2  
CB3 NA2  NA2  N 0 1 N N N 49.611 34.366 25.057 4.225  0.224  -6.707 NA2  CB3 3  
CB3 N3   N3   N 0 1 Y N N 47.869 35.909 25.049 3.187  -0.958 -5.021 N3   CB3 4  
CB3 C4   C4   C 0 1 Y N N 46.845 36.546 24.426 2.137  -1.265 -4.247 C4   CB3 5  
CB3 O4   O4   O 0 1 N N N 46.062 37.395 25.176 2.225  -2.124 -3.386 O4   CB3 6  
CB3 C4A  C4A  C 0 1 Y N N 46.591 36.303 23.071 0.872  -0.537 -4.461 C4A  CB3 7  
CB3 C5   C5   C 0 1 Y N N 45.645 37.028 22.331 -0.264 -0.796 -3.699 C5   CB3 8  
CB3 C6   C6   C 0 1 Y N N 45.422 36.746 20.961 -1.420 -0.086 -3.941 C6   CB3 9  
CB3 C7   C7   C 0 1 Y N N 46.134 35.681 20.356 -1.456 0.879  -4.936 C7   CB3 10 
CB3 C8   C8   C 0 1 Y N N 47.099 34.962 21.098 -0.338 1.146  -5.699 C8   CB3 11 
CB3 C8A  C8A  C 0 1 Y N N 47.342 35.288 22.447 0.834  0.441  -5.469 C8A  CB3 12 
CB3 C9   C9   C 0 1 N N N 44.782 37.722 20.047 -2.653 -0.361 -3.120 C9   CB3 13 
CB3 N10  N10  N 0 1 N N N 44.528 39.077 20.602 -2.657 0.506  -1.939 N10  CB3 14 
CB3 C11  C11  C 0 1 Y N N 47.396 41.799 21.930 -0.866 -0.776 1.591  C11  CB3 15 
CB3 C12  C12  C 0 1 Y N N 46.081 41.878 22.444 -0.958 -1.642 0.497  C12  CB3 16 
CB3 C13  C13  C 0 1 Y N N 45.108 40.965 22.017 -1.550 -1.215 -0.668 C13  CB3 17 
CB3 C14  C14  C 0 1 Y N N 45.443 39.963 21.073 -2.058 0.077  -0.760 C14  CB3 18 
CB3 C15  C15  C 0 1 Y N N 46.780 39.880 20.607 -1.963 0.944  0.325  C15  CB3 19 
CB3 C16  C16  C 0 1 Y N N 47.742 40.791 21.035 -1.377 0.521  1.496  C16  CB3 20 
CB3 C    C    C 0 1 N N N 48.435 42.751 22.275 -0.232 -1.231 2.842  C    CB3 21 
CB3 O    O    O 0 1 N N N 49.622 42.568 21.994 0.211  -2.360 2.924  O    CB3 22 
CB3 N    N    N 0 1 N N N 48.028 43.853 22.932 -0.144 -0.395 3.896  N    CB3 23 
CB3 CA   CA   C 0 1 N N S 48.781 45.113 23.167 0.485  -0.847 5.139  CA   CB3 24 
CB3 CB   CB   C 0 1 N N N 48.386 46.180 22.139 1.128  0.346  5.848  CB   CB3 25 
CB3 CG   CG   C 0 1 N N N 49.105 46.067 20.801 2.186  0.971  4.938  CG   CB3 26 
CB3 CD   CD   C 0 1 N N N 48.401 46.814 19.672 2.819  2.147  5.637  CD   CB3 27 
CB3 OE1  OE1  O 0 1 N N N 47.560 47.704 19.951 2.460  2.454  6.749  OE1  CB3 28 
CB3 OE2  OE2  O 0 1 N N N 48.672 46.488 18.492 3.781  2.854  5.023  OE2  CB3 29 
CB3 CT   CT   C 0 1 N N N 48.466 45.612 24.579 -0.557 -1.462 6.036  CT   CB3 30 
CB3 O1   O1   O 0 1 N N N 49.430 45.939 25.298 -0.249 -2.343 6.804  O1   CB3 31 
CB3 O2   O2   O 0 1 N N N 47.271 45.658 24.957 -1.827 -1.033 5.981  O2   CB3 32 
CB3 CP1  CP1  C 0 1 N N N 43.087 39.331 20.634 -3.291 1.825  -2.002 CP1  CB3 33 
CB3 CP2  CP2  C 0 1 N N N 42.657 39.090 21.998 -4.671 1.730  -1.499 CP2  CB3 34 
CB3 CP3  CP3  C 0 1 N N N 42.273 38.826 23.104 -5.772 1.655  -1.098 CP3  CB3 35 
CB3 HN1  HN1  H 0 1 N N N 48.123 33.653 23.104 1.980  1.351  -6.900 HN1  CB3 36 
CB3 HN21 1HN2 H 0 0 N N N 49.831 34.601 26.024 5.045  -0.268 -6.546 HN21 CB3 37 
CB3 HN22 2HN2 H 0 0 N N N 50.457 34.486 24.500 4.193  0.898  -7.404 HN22 CB3 38 
CB3 H5   H5   H 0 1 N N N 45.071 37.826 22.830 -0.239 -1.548 -2.924 H5   CB3 39 
CB3 H7   H7   H 0 1 N N N 45.936 35.411 19.304 -2.369 1.428  -5.116 H7   CB3 40 
CB3 H8   H8   H 0 1 N N N 47.664 34.143 20.622 -0.376 1.900  -6.471 H8   CB3 41 
CB3 H91  1H9  H 0 1 N N N 45.378 37.805 19.108 -3.541 -0.162 -3.720 H91  CB3 42 
CB3 H92  2H9  H 0 1 N N N 43.832 37.295 19.646 -2.654 -1.404 -2.804 H92  CB3 43 
CB3 H12  H12  H 0 1 N N N 45.813 42.654 23.180 -0.564 -2.645 0.567  H12  CB3 44 
CB3 H13  H13  H 0 1 N N N 44.084 41.034 22.421 -1.622 -1.884 -1.513 H13  CB3 45 
CB3 H15  H15  H 0 1 N N N 47.077 39.090 19.896 -2.358 1.946  0.251  H15  CB3 46 
CB3 H16  H16  H 0 1 N N N 48.778 40.714 20.665 -1.308 1.192  2.339  H16  CB3 47 
CB3 HN   HN   H 0 1 N N N 47.077 43.723 23.277 -0.498 0.505  3.831  HN   CB3 48 
CB3 HA   HA   H 0 1 N N N 49.873 44.916 23.060 1.251  -1.588 4.910  HA   CB3 49 
CB3 HB1  1HB  H 0 1 N N N 47.281 46.181 21.986 0.362  1.087  6.077  HB1  CB3 50 
CB3 HB2  2HB  H 0 1 N N N 48.522 47.200 22.567 1.596  0.010  6.773  HB2  CB3 51 
CB3 HG1  1HG  H 0 1 N N N 50.166 46.396 20.892 2.952  0.230  4.709  HG1  CB3 52 
CB3 HG2  2HG  H 0 1 N N N 49.267 44.998 20.527 1.718  1.307  4.013  HG2  CB3 53 
CB3 HOE2 2HOE H 0 0 N N N 48.233 46.953 17.789 4.187  3.608  5.472  HOE2 CB3 54 
CB3 HO2  HO2  H 0 1 N N N 47.075 45.967 25.833 -2.497 -1.428 6.556  HO2  CB3 55 
CB3 HP11 1HP1 H 0 0 N N N 42.808 40.342 20.255 -2.728 2.528  -1.388 HP11 CB3 56 
CB3 HP12 2HP1 H 0 0 N N N 42.517 38.738 19.880 -3.303 2.174  -3.035 HP12 CB3 57 
CB3 HP3  HP3  H 0 1 N N N 41.924 38.586 24.108 -6.756 1.587  -0.739 HP3  CB3 58 
# 
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 
CB3 N1  C2   SING Y N 1  
CB3 N1  C8A  SING Y N 2  
CB3 N1  HN1  SING N N 3  
CB3 C2  NA2  SING N N 4  
CB3 C2  N3   DOUB Y N 5  
CB3 NA2 HN21 SING N N 6  
CB3 NA2 HN22 SING N N 7  
CB3 N3  C4   SING Y N 8  
CB3 C4  O4   DOUB N N 9  
CB3 C4  C4A  SING Y N 10 
CB3 C4A C5   DOUB Y N 11 
CB3 C4A C8A  SING Y N 12 
CB3 C5  C6   SING Y N 13 
CB3 C5  H5   SING N N 14 
CB3 C6  C7   DOUB Y N 15 
CB3 C6  C9   SING N N 16 
CB3 C7  C8   SING Y N 17 
CB3 C7  H7   SING N N 18 
CB3 C8  C8A  DOUB Y N 19 
CB3 C8  H8   SING N N 20 
CB3 C9  N10  SING N N 21 
CB3 C9  H91  SING N N 22 
CB3 C9  H92  SING N N 23 
CB3 N10 C14  SING N N 24 
CB3 N10 CP1  SING N N 25 
CB3 C11 C12  DOUB Y N 26 
CB3 C11 C16  SING Y N 27 
CB3 C11 C    SING N N 28 
CB3 C12 C13  SING Y N 29 
CB3 C12 H12  SING N N 30 
CB3 C13 C14  DOUB Y N 31 
CB3 C13 H13  SING N N 32 
CB3 C14 C15  SING Y N 33 
CB3 C15 C16  DOUB Y N 34 
CB3 C15 H15  SING N N 35 
CB3 C16 H16  SING N N 36 
CB3 C   O    DOUB N N 37 
CB3 C   N    SING N N 38 
CB3 N   CA   SING N N 39 
CB3 N   HN   SING N N 40 
CB3 CA  CB   SING N N 41 
CB3 CA  CT   SING N N 42 
CB3 CA  HA   SING N N 43 
CB3 CB  CG   SING N N 44 
CB3 CB  HB1  SING N N 45 
CB3 CB  HB2  SING N N 46 
CB3 CG  CD   SING N N 47 
CB3 CG  HG1  SING N N 48 
CB3 CG  HG2  SING N N 49 
CB3 CD  OE1  DOUB N N 50 
CB3 CD  OE2  SING N N 51 
CB3 OE2 HOE2 SING N N 52 
CB3 CT  O1   DOUB N N 53 
CB3 CT  O2   SING N N 54 
CB3 O2  HO2  SING N N 55 
CB3 CP1 CP2  SING N N 56 
CB3 CP1 HP11 SING N N 57 
CB3 CP1 HP12 SING N N 58 
CB3 CP2 CP3  TRIP N N 59 
CB3 CP3 HP3  SING N N 60 
# 
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 
CB3 SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)N(CC#C)Cc2ccc3NC(=NC(=O)c3c2)N)CCC(=O)O 
CB3 InChI            InChI                1.02b 
InChI=1/C24H23N5O6/c1-2-11-29(13-14-3-8-18-17(12-14)22(33)28-24(25)27-18)16-6-4-15(5-7-16)21(32)26-19(23(34)35)9-10-20(30)31/h1,3-8,12,19H,9-11,13H2,(H,26,32)(H,30,31)(H,34,35)(H3,25,27,28,33)/t19-/m0/s1/f/h26-27,30,34H,25H2 
CB3 InChIKey         InChI                1.02b LTKHPMDRMUCUEB-NSDXGODUDZ 
CB3 SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)c2cc(CN(CC#C)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)ccc2N1 
CB3 SMILES           CACTVS               3.341 NC1=NC(=O)c2cc(CN(CC#C)c3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)ccc2N1 
CB3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C#CCN(Cc1ccc2c(c1)C(=O)N=C(N2)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
CB3 SMILES           "OpenEye OEToolkits" 1.5.0 C#CCN(Cc1ccc2c(c1)C(=O)N=C(N2)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 
CB3 "SYSTEMATIC NAME" ACDLabs              10.04 "N-[(4-{[(2-amino-4-oxo-1,4-dihydroquinazolin-6-yl)methyl](prop-2-yn-1-yl)amino}phenyl)carbonyl]-L-glutamic acid" 
CB3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(2-amino-4-oxo-1H-quinazolin-6-yl)methyl-prop-2-ynyl-amino]phenyl]carbonylamino]pentanedioic acid"   
# 
