data_TQD
# 
_chem_comp.id                                    TQD 
_chem_comp.name                                  (2R,6S)-6-{[methyl(3,4,5-trimethoxyphenyl)amino]methyl}-1,2,5,6,7,8-hexahydroquinazoline-2,4-diamine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H29 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-01-19 
_chem_comp.pdbx_modified_date                    2009-02-03
_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                        375.465 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TQD 
_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        1S3U 
_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 
TQD C2D    C2D    C 0 1 N N S 27.470 12.689 -4.564 4.865  1.514  0.840  C2D    TQD 1  
TQD C4D    C4D    C 0 1 N N N 27.131 12.585 -2.253 2.484  1.313  1.130  C4D    TQD 2  
TQD C4A    C4A    C 0 1 N N N 28.256 13.467 -2.021 2.546  0.006  0.455  C4A    TQD 3  
TQD C5D    C5D    C 0 1 N N N 28.819 13.707 -0.738 1.272  -0.586 -0.083 C5D    TQD 4  
TQD C6D    C6D    C 0 1 N N S 29.970 14.491 -0.624 1.443  -2.082 -0.343 C6D    TQD 5  
TQD "C7'"  "C7'"  C 0 1 N N N 30.720 14.838 -1.769 2.711  -2.285 -1.182 "C7'"  TQD 6  
TQD C8     C8     C 0 1 N N N 30.326 14.300 -3.028 3.921  -1.939 -0.315 C8     TQD 7  
TQD C8A    C8A    C 0 1 N N N 29.130 13.597 -3.131 3.735  -0.600 0.340  C8A    TQD 8  
TQD "C8'"  "C8'"  C 0 1 N N N 30.502 14.727 0.824  0.229  -2.615 -1.107 "C8'"  TQD 9  
TQD "C1'"  "C1'"  C 0 1 Y N N 32.704 15.802 0.694  -1.743 -1.343 -0.303 "C1'"  TQD 10 
TQD "C2'"  "C2'"  C 0 1 Y N N 34.055 15.545 0.520  -2.874 -1.239 0.495  "C2'"  TQD 11 
TQD "C3'"  "C3'"  C 0 1 Y N N 34.871 16.588 0.145  -3.644 -0.086 0.461  "C3'"  TQD 12 
TQD C3B    C3B    C 0 1 N N N 36.789 15.206 0.308  -5.064 -1.105 2.074  C3B    TQD 13 
TQD "C4'"  "C4'"  C 0 1 Y N N 34.379 17.864 -0.034 -3.282 0.965  -0.372 "C4'"  TQD 14 
TQD C4B    C4B    C 0 1 N N N 36.196 18.401 -1.369 -3.693 3.136  0.513  C4B    TQD 15 
TQD "C5'"  "C5'"  C 0 1 Y N N 33.006 18.109 0.145  -2.150 0.861  -1.171 "C5'"  TQD 16 
TQD C5B    C5B    C 0 1 N N N 31.350 19.720 0.055  -0.620 1.713  -2.780 C5B    TQD 17 
TQD "C6'"  "C6'"  C 0 1 Y N N 32.120 17.056 0.466  -1.382 -0.293 -1.136 "C6'"  TQD 18 
TQD "N1'"  "N1'"  N 0 1 N N N 28.819 12.999 -4.346 4.845  0.047  0.852  "N1'"  TQD 19 
TQD "N2'"  "N2'"  N 0 1 N N N 27.143 12.087 -5.687 5.106  1.992  -0.528 "N2'"  TQD 20 
TQD "N3'"  "N3'"  N 0 1 N N N 26.709 12.424 -3.474 3.571  2.014  1.312  "N3'"  TQD 21 
TQD "N4'"  "N4'"  N 0 1 N N N 26.254 12.199 -1.313 1.270  1.800  1.572  "N4'"  TQD 22 
TQD "N9'"  "N9'"  N 0 1 N N N 31.951 14.687 1.006  -0.964 -2.504 -0.264 "N9'"  TQD 23 
TQD "O3'"  "O3'"  O 0 1 N N N 36.213 16.461 -0.021 -4.752 0.015  1.243  "O3'"  TQD 24 
TQD "O4'"  "O4'"  O 0 1 N N N 35.267 18.900 -0.403 -4.038 2.098  -0.406 "O4'"  TQD 25 
TQD "O5'"  "O5'"  O 0 1 N N N 32.772 19.498 -0.116 -1.796 1.890  -1.987 "O5'"  TQD 26 
TQD "C9'"  "C9'"  C 0 1 N N N 32.660 13.475 1.355  -1.342 -3.611 0.618  "C9'"  TQD 27 
TQD "H2'"  "H2'"  H 0 1 N N N 27.113 13.699 -4.812 5.657  1.873  1.497  "H2'"  TQD 28 
TQD "H5'1" "H5'1" H 0 0 N N N 28.041 14.217 -0.152 0.472  -0.437 0.642  "H5'1" TQD 29 
TQD "H5'2" "H5'2" H 0 0 N N N 29.145 12.711 -0.403 1.009  -0.087 -1.015 "H5'2" TQD 30 
TQD "H6'"  "H6'"  H 0 1 N N N 29.666 15.524 -0.847 1.542  -2.611 0.605  "H6'"  TQD 31 
TQD "H7'1" "H7'1" H 0 0 N N N 30.661 15.932 -1.863 2.775  -3.324 -1.506 "H7'1" TQD 32 
TQD "H7'2" "H7'2" H 0 0 N N N 31.716 14.409 -1.586 2.684  -1.630 -2.053 "H7'2" TQD 33 
TQD H81    H81    H 0 1 N N N 30.240 15.155 -3.714 4.042  -2.702 0.454  H81    TQD 34 
TQD H82    H82    H 0 1 N N N 31.095 13.544 -3.244 4.815  -1.913 -0.939 H82    TQD 35 
TQD "H8'1" "H8'1" H 0 0 N N N 30.164 15.727 1.134  0.087  -2.030 -2.016 "H8'1" TQD 36 
TQD "H8'2" "H8'2" H 0 0 N N N 30.108 13.891 1.421  0.394  -3.660 -1.368 "H8'2" TQD 37 
TQD "H2'1" "H2'1" H 0 0 N N N 34.456 14.554 0.674  -3.155 -2.056 1.143  "H2'1" TQD 38 
TQD H3B1   H3B1   H 0 0 N N N 36.938 14.618 -0.610 -5.969 -0.893 2.644  H3B1   TQD 39 
TQD H3B2   H3B2   H 0 0 N N N 37.759 15.366 0.802  -5.223 -1.986 1.453  H3B2   TQD 40 
TQD H3B3   H3B3   H 0 0 N N N 36.117 14.661 0.987  -4.237 -1.289 2.761  H3B3   TQD 41 
TQD H4B1   H4B1   H 0 0 N N N 35.687 18.273 -2.336 -2.669 3.461  0.326  H4B1   TQD 42 
TQD H4B2   H4B2   H 0 0 N N N 37.025 19.115 -1.483 -4.371 3.979  0.381  H4B2   TQD 43 
TQD H4B3   H4B3   H 0 0 N N N 36.590 17.431 -1.031 -3.774 2.760  1.533  H4B3   TQD 44 
TQD H5B1   H5B1   H 0 0 N N N 31.114 19.776 1.128  -0.451 2.606  -3.383 H5B1   TQD 45 
TQD H5B2   H5B2   H 0 0 N N N 31.065 20.664 -0.433 0.237  1.549  -2.127 H5B2   TQD 46 
TQD H5B3   H5B3   H 0 0 N N N 30.792 18.888 -0.400 -0.749 0.851  -3.434 H5B3   TQD 47 
TQD "H6'1" "H6'1" H 0 0 N N N 31.053 17.209 0.532  -0.502 -0.374 -1.757 "H6'1" TQD 48 
TQD H1D    H1D    H 0 1 N N N 29.331 12.141 -4.392 5.593  -0.457 1.209  H1D    TQD 49 
TQD H2A1   H2A1   H 0 0 N N N 27.060 12.765 -6.417 5.124  3.000  -0.561 H2A1   TQD 50 
TQD H2A2   H2A2   H 0 0 N N N 27.851 11.423 -5.928 5.959  1.602  -0.902 H2A2   TQD 51 
TQD "H4'1" "H4'1" H 0 0 N N N 26.591 12.457 -0.407 0.461  1.281  1.438  "H4'1" TQD 52 
TQD "H4'2" "H4'2" H 0 0 N N N 25.392 11.724 -1.492 1.225  2.661  2.017  "H4'2" TQD 53 
TQD "H9'1" "H9'1" H 0 0 N N N 32.840 12.880 0.447  -0.867 -3.478 1.590  "H9'1" TQD 54 
TQD "H9'2" "H9'2" H 0 0 N N N 33.623 13.734 1.820  -2.425 -3.623 0.742  "H9'2" TQD 55 
TQD "H9'3" "H9'3" H 0 0 N N N 32.056 12.889 2.063  -1.016 -4.554 0.180  "H9'3" TQD 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 
TQD C2D   "N1'"  SING N N 1  
TQD C2D   "N2'"  SING N N 2  
TQD C2D   "N3'"  SING N N 3  
TQD C2D   "H2'"  SING N N 4  
TQD C4D   C4A    SING N N 5  
TQD C4D   "N3'"  DOUB N N 6  
TQD C4D   "N4'"  SING N N 7  
TQD C4A   C5D    SING N N 8  
TQD C4A   C8A    DOUB N N 9  
TQD C5D   C6D    SING N N 10 
TQD C5D   "H5'1" SING N N 11 
TQD C5D   "H5'2" SING N N 12 
TQD C6D   "C7'"  SING N N 13 
TQD C6D   "C8'"  SING N N 14 
TQD C6D   "H6'"  SING N N 15 
TQD "C7'" C8     SING N N 16 
TQD "C7'" "H7'1" SING N N 17 
TQD "C7'" "H7'2" SING N N 18 
TQD C8    C8A    SING N N 19 
TQD C8    H81    SING N N 20 
TQD C8    H82    SING N N 21 
TQD C8A   "N1'"  SING N N 22 
TQD "C8'" "N9'"  SING N N 23 
TQD "C8'" "H8'1" SING N N 24 
TQD "C8'" "H8'2" SING N N 25 
TQD "C1'" "C2'"  DOUB Y N 26 
TQD "C1'" "C6'"  SING Y N 27 
TQD "C1'" "N9'"  SING N N 28 
TQD "C2'" "C3'"  SING Y N 29 
TQD "C2'" "H2'1" SING N N 30 
TQD "C3'" "C4'"  DOUB Y N 31 
TQD "C3'" "O3'"  SING N N 32 
TQD C3B   "O3'"  SING N N 33 
TQD C3B   H3B1   SING N N 34 
TQD C3B   H3B2   SING N N 35 
TQD C3B   H3B3   SING N N 36 
TQD "C4'" "C5'"  SING Y N 37 
TQD "C4'" "O4'"  SING N N 38 
TQD C4B   "O4'"  SING N N 39 
TQD C4B   H4B1   SING N N 40 
TQD C4B   H4B2   SING N N 41 
TQD C4B   H4B3   SING N N 42 
TQD "C5'" "C6'"  DOUB Y N 43 
TQD "C5'" "O5'"  SING N N 44 
TQD C5B   "O5'"  SING N N 45 
TQD C5B   H5B1   SING N N 46 
TQD C5B   H5B2   SING N N 47 
TQD C5B   H5B3   SING N N 48 
TQD "C6'" "H6'1" SING N N 49 
TQD "N1'" H1D    SING N N 50 
TQD "N2'" H2A1   SING N N 51 
TQD "N2'" H2A2   SING N N 52 
TQD "N4'" "H4'1" SING N N 53 
TQD "N4'" "H4'2" SING N N 54 
TQD "N9'" "C9'"  SING N N 55 
TQD "C9'" "H9'1" SING N N 56 
TQD "C9'" "H9'2" SING N N 57 
TQD "C9'" "H9'3" 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 
TQD InChI            InChI                1.02b InChI=1/C19H29N5O3/c1-24(12-8-15(25-2)17(27-4)16(9-12)26-3)10-11-5-6-14-13(7-11)18(20)23-19(21)22-14/h8-9,11,19,22H,5-7,10,21H2,1-4H3,(H2,20,23)/t11-,19+/m0/s1/f/h20H2 
TQD InChIKey         InChI                1.02b JJWPLCQODKLEHY-BISYDJDLDE                                                                                                                                               
TQD SMILES_CANONICAL CACTVS               3.352 COc1cc(cc(OC)c1OC)N(C)C[C@H]2CCC3=C(C2)C(=N[C@H](N)N3)N                                                                                                                 
TQD SMILES           CACTVS               3.352 COc1cc(cc(OC)c1OC)N(C)C[CH]2CCC3=C(C2)C(=N[CH](N)N3)N                                                                                                                   
TQD SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 CN(CC1CCC2=C(C1)C(=N[C@@H](N2)N)N)c3cc(c(c(c3)OC)OC)OC                                                                                                                  
TQD SMILES           "OpenEye OEToolkits" 1.6.1 CN(CC1CCC2=C(C1)C(=NC(N2)N)N)c3cc(c(c(c3)OC)OC)OC                                                                                                                       
# 
_pdbx_chem_comp_identifier.comp_id           TQD 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   1.6.1 
_pdbx_chem_comp_identifier.identifier        (2R)-6-[[methyl-(3,4,5-trimethoxyphenyl)amino]methyl]-1,2,5,6,7,8-hexahydroquinazoline-2,4-diamine 
# 
