data_DHF
# 
_chem_comp.id                                    DHF 
_chem_comp.name                                  "DIHYDROFOLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H21 N7 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                        443.413 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DHF 
_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        1TYS 
_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 
DHF N1   N1   N 0 1 Y N N 29.878 -19.583 35.230 -1.152 0.282  7.878  N1   DHF 1  
DHF C2   C2   C 0 1 Y N N 28.579 -19.533 34.912 -0.084 -0.259 8.529  C2   DHF 2  
DHF NA2  NA2  N 0 1 N N N 28.154 -19.940 33.713 -0.116 -0.360 9.895  NA2  DHF 3  
DHF N3   N3   N 0 1 Y N N 27.671 -19.217 35.832 0.974  -0.691 7.880  N3   DHF 4  
DHF C4   C4   C 0 1 Y N N 28.040 -19.002 37.103 1.057  -0.613 6.542  C4   DHF 5  
DHF O4   O4   O 0 1 N N N 27.115 -18.534 38.002 2.049  -1.024 5.958  O4   DHF 6  
DHF C4A  C4A  C 0 1 Y N N 29.383 -19.062 37.460 -0.021 -0.049 5.814  C4A  DHF 7  
DHF N5   N5   N 0 1 N N N 29.812 -18.741 38.664 0.007  0.049  4.455  N5   DHF 8  
DHF C6   C6   C 0 1 N N N 31.066 -19.036 39.047 -0.842 0.770  3.810  C6   DHF 9  
DHF C7   C7   C 0 1 N N N 32.081 -19.332 38.059 -1.892 1.574  4.533  C7   DHF 10 
DHF N8   N8   N 0 1 N N N 31.592 -19.072 36.698 -2.191 0.924  5.819  N8   DHF 11 
DHF C8A  C8A  C 0 1 Y N N 30.300 -19.320 36.454 -1.134 0.393  6.520  C8A  DHF 12 
DHF C9   C9   C 0 1 N N N 31.434 -19.087 40.477 -0.785 0.812  2.305  C9   DHF 13 
DHF N10  N10  N 0 1 N N N 30.244 -19.210 41.350 0.308  -0.040 1.834  N10  DHF 14 
DHF C11  C11  C 0 1 Y N N 27.946 -22.667 41.190 1.055  -0.405 -2.243 C11  DHF 15 
DHF C12  C12  C 0 1 Y N N 29.142 -22.639 40.499 1.847  -1.096 -1.322 C12  DHF 16 
DHF C13  C13  C 0 1 Y N N 29.914 -21.501 40.559 1.598  -0.973 0.025  C13  DHF 17 
DHF C14  C14  C 0 1 Y N N 29.513 -20.365 41.289 0.558  -0.162 0.471  C14  DHF 18 
DHF C15  C15  C 0 1 Y N N 28.293 -20.413 41.962 -0.236 0.522  -0.443 C15  DHF 19 
DHF C16  C16  C 0 1 Y N N 27.510 -21.557 41.913 0.011  0.408  -1.792 C16  DHF 20 
DHF C    C    C 0 1 N N N 27.212 -23.898 41.224 1.320  -0.534 -3.689 C    DHF 21 
DHF O    O    O 0 1 N N N 27.456 -24.835 40.464 2.228  -1.242 -4.080 O    DHF 22 
DHF N    N    N 0 1 N N N 26.229 -23.992 42.111 0.555  0.132  -4.576 N    DHF 23 
DHF CA   CA   C 0 1 N N S 25.399 -25.197 42.162 0.818  0.004  -6.011 CA   DHF 24 
DHF CB   CB   C 0 1 N N N 26.080 -26.251 43.087 -0.489 0.175  -6.787 CB   DHF 25 
DHF CG   CG   C 0 1 N N N 26.649 -25.761 44.421 -1.484 -0.903 -6.353 CG   DHF 26 
DHF CD   CD   C 0 1 N N N 27.617 -26.736 45.099 -2.772 -0.735 -7.116 CD   DHF 27 
DHF OE1  OE1  O 0 1 N N N 28.766 -26.898 44.671 -2.883 0.155  -7.925 OE1  DHF 28 
DHF OE2  OE2  O 0 1 N N N 27.243 -27.331 46.108 -3.796 -1.574 -6.898 OE2  DHF 29 
DHF CT   CT   C 0 1 N N N 23.984 -24.885 42.617 1.798  1.066  -6.439 CT   DHF 30 
DHF O1   O1   O 0 1 N N N 23.131 -25.730 42.379 2.552  0.857  -7.360 O1   DHF 31 
DHF O2   O2   O 0 1 N N N 23.711 -23.801 43.135 1.833  2.244  -5.798 O2   DHF 32 
DHF HN1  HN1  H 0 1 N N N 30.382 -18.973 34.586 -1.921 0.594  8.381  HN1  DHF 33 
DHF HN21 1HN2 H 0 0 N N N 27.163 -19.901 33.470 0.635  -0.747 10.370 HN21 DHF 34 
DHF HN22 2HN2 H 0 0 N N N 28.481 -20.895 33.566 -0.889 -0.041 10.386 HN22 DHF 35 
DHF H71  1H7  H 0 1 N N N 33.027 -18.780 38.266 -2.798 1.619  3.928  H71  DHF 36 
DHF H72  2H7  H 0 1 N N N 32.463 -20.374 38.164 -1.521 2.584  4.711  H72  DHF 37 
DHF HN8  HN8  H 0 1 N N N 32.167 -19.582 36.027 -3.098 0.873  6.159  HN8  DHF 38 
DHF H91  1H9  H 0 1 N N N 32.169 -19.900 40.677 -1.728 0.452  1.896  H91  DHF 39 
DHF H92  2H9  H 0 1 N N N 32.059 -18.210 40.765 -0.614 1.837  1.976  H92  DHF 40 
DHF HN0  HN0  H 0 1 N N N 29.625 -18.415 41.184 0.859  -0.520 2.472  HN0  DHF 41 
DHF H12  H12  H 0 1 N N N 29.474 -23.510 39.909 2.654  -1.725 -1.667 H12  DHF 42 
DHF H13  H13  H 0 1 N N N 30.871 -21.499 40.011 2.209  -1.507 0.738  H13  DHF 43 
DHF H15  H15  H 0 1 N N N 27.944 -19.539 42.537 -1.042 1.150  -0.094 H15  DHF 44 
DHF H16  H16  H 0 1 N N N 26.545 -21.583 42.446 -0.601 0.943  -2.502 H16  DHF 45 
DHF HN   HN   H 0 1 N N N 26.117 -23.181 42.720 -0.169 0.697  -4.264 HN   DHF 46 
DHF HA   HA   H 0 1 N N N 25.312 -25.619 41.133 1.237  -0.980 -6.218 HA   DHF 47 
DHF HB1  1HB  H 0 1 N N N 25.369 -27.089 43.275 -0.908 1.160  -6.581 HB1  DHF 48 
DHF HB2  2HB  H 0 1 N N N 26.880 -26.778 42.517 -0.293 0.079  -7.855 HB2  DHF 49 
DHF HG1  1HG  H 0 1 N N N 27.130 -24.763 44.293 -1.065 -1.888 -6.559 HG1  DHF 50 
DHF HG2  2HG  H 0 1 N N N 25.822 -25.488 45.117 -1.679 -0.807 -5.285 HG2  DHF 51 
DHF HOE2 2HOE H 0 0 N N N 27.843 -27.935 46.528 -4.623 -1.466 -7.388 HOE2 DHF 52 
DHF HO2  HO2  H 0 1 N N N 22.825 -23.605 43.419 2.462  2.926  -6.072 HO2  DHF 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 
DHF N1  C2   SING Y N 1  
DHF N1  C8A  SING Y N 2  
DHF N1  HN1  SING N N 3  
DHF C2  NA2  SING N N 4  
DHF C2  N3   DOUB Y N 5  
DHF NA2 HN21 SING N N 6  
DHF NA2 HN22 SING N N 7  
DHF N3  C4   SING Y N 8  
DHF C4  O4   DOUB N N 9  
DHF C4  C4A  SING Y N 10 
DHF C4A N5   SING N N 11 
DHF C4A C8A  DOUB Y N 12 
DHF N5  C6   DOUB N N 13 
DHF C6  C7   SING N N 14 
DHF C6  C9   SING N N 15 
DHF C7  N8   SING N N 16 
DHF C7  H71  SING N N 17 
DHF C7  H72  SING N N 18 
DHF N8  C8A  SING N N 19 
DHF N8  HN8  SING N N 20 
DHF C9  N10  SING N N 21 
DHF C9  H91  SING N N 22 
DHF C9  H92  SING N N 23 
DHF N10 C14  SING N N 24 
DHF N10 HN0  SING N N 25 
DHF C11 C12  DOUB Y N 26 
DHF C11 C16  SING Y N 27 
DHF C11 C    SING N N 28 
DHF C12 C13  SING Y N 29 
DHF C12 H12  SING N N 30 
DHF C13 C14  DOUB Y N 31 
DHF C13 H13  SING N N 32 
DHF C14 C15  SING Y N 33 
DHF C15 C16  DOUB Y N 34 
DHF C15 H15  SING N N 35 
DHF C16 H16  SING N N 36 
DHF C   O    DOUB N N 37 
DHF C   N    SING N N 38 
DHF N   CA   SING N N 39 
DHF N   HN   SING N N 40 
DHF CA  CB   SING N N 41 
DHF CA  CT   SING N N 42 
DHF CA  HA   SING N N 43 
DHF CB  CG   SING N N 44 
DHF CB  HB1  SING N N 45 
DHF CB  HB2  SING N N 46 
DHF CG  CD   SING N N 47 
DHF CG  HG1  SING N N 48 
DHF CG  HG2  SING N N 49 
DHF CD  OE1  DOUB N N 50 
DHF CD  OE2  SING N N 51 
DHF OE2 HOE2 SING N N 52 
DHF CT  O1   DOUB N N 53 
DHF CT  O2   SING N N 54 
DHF O2  HO2  SING N N 55 
# 
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 
DHF SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)c1ccc(cc1)NCC2=NC=3C(=O)N=C(NC=3NC2)N)CCC(=O)O 
DHF InChI            InChI                1.02b 
InChI=1/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1/f/h22,24-25,27,31H,20H2 
DHF InChIKey         InChI                1.02b OZRNSSUDZOLUSN-FXKQMYAYDV 
DHF SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)C2=C(NCC(=N2)CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N1 
DHF SMILES           CACTVS               3.341 NC1=NC(=O)C2=C(NCC(=N2)CNc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)N1 
DHF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=NC3=C(NC2)NC(=NC3=O)N 
DHF SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=NC3=C(NC2)NC(=NC3=O)N 
# 
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 
DHF "SYSTEMATIC NAME" ACDLabs              10.04 "N-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid"       
DHF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)methylamino]phenyl]carbonylamino]pentanedioic acid" 
# 
