data_3BI
# 
_chem_comp.id                                    3BI 
_chem_comp.name                                  "(2S)-2-{[(R)-[(3R)-3-carboxy-3-{[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)carbonyl]amino}propyl](hydroxy)phosphoryl]methyl}pentanedioic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H31 N8 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-30 
_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                        618.536 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3BI 
_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        3BI1 
_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 
3BI N1   N1   N 0 1 N N N 34.263 47.850 41.929 11.422  1.039  -1.315 N1   3BI 1  
3BI C2   C2   C 0 1 Y N N 30.836 50.132 41.997 8.248   -1.264 -0.178 C2   3BI 2  
3BI N3   N3   N 0 1 N N N 32.353 52.079 42.267 9.176   -3.057 -1.612 N3   3BI 3  
3BI C4   C4   C 0 1 Y N N 28.377 48.910 41.767 6.482   -0.183 1.526  C4   3BI 4  
3BI N5   N5   N 0 1 Y N N 29.482 48.110 41.740 7.506   0.557  1.156  N5   3BI 5  
3BI C6   C6   C 0 1 N N N 27.322 51.322 41.969 5.146   -2.306 1.481  C6   3BI 6  
3BI C7   C7   C 0 1 N N N 26.232 50.511 39.980 3.997   -3.120 -0.630 C7   3BI 7  
3BI C9   C9   C 0 1 Y N N 24.021 49.862 44.245 2.253   0.713  1.820  C9   3BI 8  
3BI C11  C11  C 0 1 Y N N 25.137 50.296 42.131 3.121   -1.175 0.622  C11  3BI 9  
3BI C12  C12  C 0 1 Y N N 24.507 49.174 41.600 2.100   -1.059 -0.318 C12  3BI 10 
3BI C13  C13  C 0 1 Y N N 23.645 48.400 42.376 1.158   -0.063 -0.194 C13  3BI 11 
3BI C14  C14  C 0 1 N N N 22.541 47.800 44.506 0.219   1.900  1.014  C14  3BI 12 
3BI C15  C15  C 0 1 N N R 20.829 46.104 44.824 -1.771  3.075  0.241  C15  3BI 13 
3BI C16  C16  C 0 1 N N N 20.330 46.542 46.183 -1.248  4.342  -0.383 C16  3BI 14 
3BI C    C    C 0 1 Y N N 33.128 48.584 41.956 10.349  0.255  -0.934 C    3BI 15 
3BI O    O    O 0 1 N N N 22.945 47.621 45.783 0.280   2.678  1.947  O    3BI 16 
3BI N    N    N 0 1 Y N N 31.895 47.956 41.840 9.469   0.766  -0.097 N    3BI 17 
3BI O1   O1   O 0 1 N N N 20.293 45.816 47.231 -2.000  5.454  -0.376 O1   3BI 18 
3BI O2   O2   O 0 1 N N N 19.892 47.668 46.198 -0.151  4.359  -0.889 O2   3BI 19 
3BI O8   O8   O 0 1 N N N 18.217 42.972 42.848 -6.118  2.089  -0.671 O8   3BI 20 
3BI P    P    P 0 1 N N R 17.529 43.913 43.850 -5.195  0.934  -0.598 P    3BI 21 
3BI O7   O7   O 0 1 N N N 16.674 42.902 44.885 -4.849  0.428  -2.086 O7   3BI 22 
3BI C19  C19  C 0 1 N N N 16.397 44.960 43.042 -5.985  -0.417 0.336  C19  3BI 23 
3BI C20  C20  C 0 1 N N S 15.915 44.518 41.623 -7.335  -0.755 -0.301 C20  3BI 24 
3BI C24  C24  C 0 1 N N N 17.068 44.570 40.603 -8.337  0.314  0.049  C24  3BI 25 
3BI O6   O6   O 0 1 N N N 17.955 45.451 40.695 -8.006  1.251  0.737  O6   3BI 26 
3BI O5   O5   O 0 1 N N N 17.052 43.758 39.619 -9.598  0.227  -0.404 O5   3BI 27 
3BI C21  C21  C 0 1 N N N 14.664 45.279 41.108 -7.824  -2.105 0.227  C21  3BI 28 
3BI C22  C22  C 0 1 N N N 14.941 46.755 41.058 -9.110  -2.502 -0.501 C22  3BI 29 
3BI C23  C23  C 0 1 N N N 13.811 47.541 40.404 -9.592  -3.831 0.020  C23  3BI 30 
3BI O4   O4   O 0 1 N N N 13.065 46.989 39.525 -10.712 -4.380 -0.477 O4   3BI 31 
3BI O3   O3   O 0 1 N N N 13.732 48.774 40.673 -8.971  -4.403 0.884  O3   3BI 32 
3BI C18  C18  C 0 1 N N N 18.689 44.860 44.713 -3.658  1.437  0.245  C18  3BI 33 
3BI C17  C17  C 0 1 N N N 19.669 45.646 43.892 -3.060  2.652  -0.467 C17  3BI 34 
3BI N7   N7   N 0 1 N N N 21.584 47.091 44.024 -0.770  2.014  0.105  N7   3BI 35 
3BI C8   C8   C 0 1 Y N N 23.392 48.735 43.691 1.227   0.832  0.878  C8   3BI 36 
3BI C10  C10  C 0 1 Y N N 24.868 50.655 43.462 3.192   -0.285 1.690  C10  3BI 37 
3BI N6   N6   N 0 1 N N N 26.007 51.085 41.310 4.071   -2.182 0.493  N6   3BI 38 
3BI C3   C3   C 0 1 Y N N 28.484 50.317 41.896 6.328   -1.481 1.042  C3   3BI 39 
3BI N4   N4   N 0 1 Y N N 29.721 50.871 42.012 7.206   -1.994 0.207  N4   3BI 40 
3BI C5   C5   C 0 1 Y N N 30.719 48.658 41.858 8.409   0.056  0.310  C5   3BI 41 
3BI C1   C1   C 0 1 Y N N 32.201 50.734 42.125 9.262   -1.781 -1.100 C1   3BI 42 
3BI N2   N2   N 0 1 Y N N 33.274 49.922 42.105 10.264  -0.977 -1.426 N2   3BI 43 
3BI HN1  HN1  H 0 1 N N N 34.521 47.669 40.980 11.511  1.940  -0.968 HN1  3BI 44 
3BI HN1A HN1A H 0 0 N N N 34.997 48.355 42.383 12.087  0.687  -1.927 HN1A 3BI 45 
3BI HN3  HN3  H 0 1 N N N 32.390 52.310 43.239 8.434   -3.631 -1.363 HN3  3BI 46 
3BI HN3A HN3A H 0 0 N N N 33.202 52.367 41.823 9.857   -3.382 -2.222 HN3A 3BI 47 
3BI H4   H4   H 0 1 N N N 27.398 48.460 41.688 5.752   0.221  2.211  H4   3BI 48 
3BI H6   H6   H 0 1 N N N 27.710 52.246 41.516 4.793   -1.949 2.448  H6   3BI 49 
3BI H6A  H6A  H 0 1 N N N 27.055 51.289 43.036 5.443   -3.351 1.566  H6A  3BI 50 
3BI H7   H7   H 0 1 N N N 26.288 51.319 39.236 3.389   -3.980 -0.346 H7   3BI 51 
3BI H7A  H7A  H 0 1 N N N 27.176 49.946 39.980 3.545   -2.624 -1.488 H7A  3BI 52 
3BI H9   H9   H 0 1 N N N 23.850 50.118 45.280 2.312   1.406  2.646  H9   3BI 53 
3BI H12  H12  H 0 1 N N N 24.689 48.899 40.572 2.047   -1.751 -1.145 H12  3BI 54 
3BI H13  H13  H 0 1 N N N 23.171 47.531 41.944 0.367   0.026  -0.923 H13  3BI 55 
3BI H15  H15  H 0 1 N N N 21.516 45.297 45.118 -1.976  3.247  1.298  H15  3BI 56 
3BI H19  H19  H 0 1 N N N 15.504 45.025 43.681 -5.343  -1.298 0.314  H19  3BI 57 
3BI H19A H19A H 0 0 N N N 16.936 45.906 42.885 -6.139  -0.105 1.368  H19A 3BI 58 
3BI H20  H20  H 0 1 N N N 15.590 43.473 41.734 -7.223  -0.808 -1.384 H20  3BI 59 
3BI H21  H21  H 0 1 N N N 14.413 44.923 40.098 -7.060  -2.862 0.053  H21  3BI 60 
3BI H21A H21A H 0 0 N N N 13.823 45.093 41.792 -8.021  -2.027 1.296  H21A 3BI 61 
3BI H22  H22  H 0 1 N N N 15.068 47.120 42.088 -9.875  -1.745 -0.326 H22  3BI 62 
3BI H22A H22A H 0 0 N N N 15.848 46.906 40.453 -8.913  -2.580 -1.570 H22A 3BI 63 
3BI H18  H18  H 0 1 N N N 18.127 45.582 45.323 -3.880  1.696  1.281  H18  3BI 64 
3BI H18A H18A H 0 0 N N N 19.296 44.136 45.276 -2.944  0.614  0.221  H18A 3BI 65 
3BI H17  H17  H 0 1 N N N 19.171 46.524 43.455 -3.774  3.476  -0.442 H17  3BI 66 
3BI H17A H17A H 0 0 N N N 20.063 45.024 43.074 -2.839  2.394  -1.502 H17A 3BI 67 
3BI HN7  HN7  H 0 1 N N N 21.338 47.213 43.062 -0.818  1.393  -0.639 HN7  3BI 68 
3BI H10  H10  H 0 1 N N N 25.315 51.544 43.882 3.985   -0.377 2.417  H10  3BI 69 
3BI H27  H27  H 0 1 N N N 12.486 47.640 39.146 -10.982 -5.234 -0.112 H27  3BI 70 
3BI H28  H28  H 0 1 N N N 16.513 42.071 44.455 -4.247  -0.328 -2.115 H28  3BI 71 
3BI H29  H29  H 0 1 N N N 19.891 46.303 47.940 -1.622  6.243  -0.789 H29  3BI 72 
3BI H30  H30  H 0 1 N N N 17.779 43.949 39.038 -10.205 0.937  -0.153 H30  3BI 73 
3BI H7B  H7B  H 0 1 N N N 25.401 49.837 39.726 5.001   -3.455 -0.890 H7B  3BI 74 
# 
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 
3BI N1  C    SING N N 1  
3BI N1  HN1  SING N N 2  
3BI N1  HN1A SING N N 3  
3BI C2  N4   DOUB Y N 4  
3BI C2  C5   SING Y N 5  
3BI C2  C1   SING Y N 6  
3BI N3  C1   SING N N 7  
3BI N3  HN3  SING N N 8  
3BI N3  HN3A SING N N 9  
3BI C4  N5   SING Y N 10 
3BI C4  C3   DOUB Y N 11 
3BI C4  H4   SING N N 12 
3BI N5  C5   DOUB Y N 13 
3BI C6  N6   SING N N 14 
3BI C6  C3   SING N N 15 
3BI C6  H6   SING N N 16 
3BI C6  H6A  SING N N 17 
3BI C7  N6   SING N N 18 
3BI C7  H7   SING N N 19 
3BI C7  H7A  SING N N 20 
3BI C9  C8   DOUB N N 21 
3BI C9  C10  SING Y N 22 
3BI C9  H9   SING Y N 23 
3BI C11 C12  SING N N 24 
3BI C11 C10  DOUB Y N 25 
3BI C11 N6   SING Y N 26 
3BI C12 C13  DOUB N N 27 
3BI C12 H12  SING Y N 28 
3BI C13 C8   SING N N 29 
3BI C13 H13  SING Y N 30 
3BI C14 O    DOUB N N 31 
3BI C14 N7   SING N N 32 
3BI C14 C8   SING N N 33 
3BI C15 C16  SING N N 34 
3BI C15 C17  SING N N 35 
3BI C15 N7   SING N N 36 
3BI C15 H15  SING N N 37 
3BI C16 O1   SING N N 38 
3BI C16 O2   DOUB N N 39 
3BI C   N    DOUB N N 40 
3BI C   N2   SING Y N 41 
3BI N   C5   SING Y N 42 
3BI O8  P    DOUB Y N 43 
3BI P   O7   SING N N 44 
3BI P   C19  SING N N 45 
3BI P   C18  SING N N 46 
3BI C19 C20  SING N N 47 
3BI C19 H19  SING N N 48 
3BI C19 H19A SING N N 49 
3BI C20 C24  SING N N 50 
3BI C20 C21  SING N N 51 
3BI C20 H20  SING N N 52 
3BI C24 O6   DOUB N N 53 
3BI C24 O5   SING N N 54 
3BI C21 C22  SING N N 55 
3BI C21 H21  SING N N 56 
3BI C21 H21A SING N N 57 
3BI C22 C23  SING N N 58 
3BI C22 H22  SING N N 59 
3BI C22 H22A SING N N 60 
3BI C23 O4   SING N N 61 
3BI C23 O3   DOUB N N 62 
3BI C18 C17  SING N N 63 
3BI C18 H18  SING N N 64 
3BI C18 H18A SING N N 65 
3BI C17 H17  SING N N 66 
3BI C17 H17A SING N N 67 
3BI N7  HN7  SING N N 68 
3BI C10 H10  SING N N 69 
3BI C3  N4   SING N N 70 
3BI C1  N2   DOUB N N 71 
3BI O4  H27  SING N N 72 
3BI O7  H28  SING N N 73 
3BI O1  H29  SING N N 74 
3BI O5  H30  SING Y N 75 
3BI C7  H7B  SING Y N 76 
# 
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 
3BI SMILES           ACDLabs              10.04 O=C(O)C(CCC(=O)O)CP(=O)(O)CCC(C(=O)O)NC(=O)c1ccc(cc1)N(C)Cc2nc3c(nc2)nc(nc3N)N 
3BI InChI            InChI                1.02b 
;InChI=1/C25H31N8O9P/c1-33(11-15-10-28-21-19(29-15)20(26)31-25(27)32-21)16-5-2-13(3-6-16)22(36)30-17(24(39)40)8-9-43(41,42)12-14(23(37)38)4-7-18(34)35/h2-3,5-6,10,14,17H,4,7-9,11-12H2,1H3,(H,30,36)(H,34,35)(H,37,38)(H,39,40)(H,41,42)(H4,26,27,28,31,32)/t14-,17-/m1/s1/f/h30,34,37,39,41H,26-27H2
;
3BI InChIKey         InChI                1.02b BHCAHIKEPKIXJL-BBATUYSFDJ 
3BI SMILES_CANONICAL CACTVS               3.341 CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@H](CC[P@](O)(=O)C[C@@H](CCC(O)=O)C(O)=O)C(O)=O 
3BI SMILES           CACTVS               3.341 CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[CH](CC[P](O)(=O)C[CH](CCC(O)=O)C(O)=O)C(O)=O 
3BI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[N@](Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)N[C@H](CC[P@](=O)(C[C@@H](CCC(=O)O)C(=O)O)O)C(=O)O 
3BI SMILES           "OpenEye OEToolkits" 1.5.0 CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)NC(CCP(=O)(CC(CCC(=O)O)C(=O)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 
3BI "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-2-{[(R)-[(3R)-3-carboxy-3-{[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)carbonyl]amino}propyl](hydroxy)phosphoryl]methyl}pentanedioic acid" 
3BI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[[(3R)-3-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]phenyl]carbonylamino]-4-hydroxy-4-oxo-butyl]-hydroxy-phosphoryl]methyl]pentanedioic acid"   
# 
