data_TTG
# 
_chem_comp.id                                    TTG 
_chem_comp.name                                  "2-(1-DIMETHYLAMINOMETHYL-2-HYDROXY-8-HYDROXYMETHYL-9-OXO-9,11-DIHYDRO-INDOLIZINO[1,2-B]QUINOLIN-7-YL)-2-HYDROXY-BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H25 N3 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "HYDROLYZED PRODUCT OF TOPOTECAN" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-01-15 
_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                        439.461 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TTG 
_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        1K4T 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
TTG C25  C25  C 0 1 N N N 19.397 1.911   29.079 -2.333 0.621  -3.917 C25  TTG 1  
TTG C31  C31  C 0 1 N N N 18.526 1.004   29.979 -3.223 0.716  -5.158 C31  TTG 2  
TTG C21  C21  C 0 1 N N S 20.032 1.341   27.761 -1.003 -0.034 -4.291 C21  TTG 3  
TTG O24  O24  O 0 1 N N N 18.946 0.823   26.981 -1.246 -1.345 -4.804 O24  TTG 4  
TTG C16  C16  C 0 1 Y N N 21.031 0.150   28.110 -0.127 -0.127 -3.069 C16  TTG 5  
TTG C20  C20  C 0 1 N N N 20.572 2.554   26.855 -0.312 0.795  -5.342 C20  TTG 6  
TTG C15  C15  C 0 1 Y N N 22.387 0.303   28.348 1.228  -0.212 -3.198 C15  TTG 7  
TTG C17  C17  C 0 1 Y N N 20.524 -1.140  28.223 -0.695 -0.121 -1.792 C17  TTG 8  
TTG O23  O23  O 0 1 N N N 20.606 2.461   25.602 -0.025 0.303  -6.408 O23  TTG 9  
TTG O22  O22  O 0 1 N N N 20.978 3.613   27.389 -0.015 2.080  -5.095 O22  TTG 10 
TTG C14  C14  C 0 1 Y N N 23.342 -0.943  28.501 2.030  -0.297 -2.047 C14  TTG 11 
TTG C19  C19  C 0 1 N N N 23.076 1.647   28.475 1.861  -0.213 -4.565 C19  TTG 12 
TTG C13  C13  C 0 1 Y N N 21.271 -2.267  28.394 0.112  -0.212 -0.677 C13  TTG 13 
TTG O18  O18  O 0 1 N N N 24.567 -0.835  28.649 3.243  -0.373 -2.158 O18  TTG 14 
TTG N12  N12  N 0 1 Y N N 22.715 -2.143  28.483 1.468  -0.296 -0.821 N12  TTG 15 
TTG C9   C9   C 0 1 Y N N 21.005 -3.741  28.466 -0.241 -0.231 0.761  C9   TTG 16 
TTG C11  C11  C 0 1 N N N 23.413 -3.450  28.526 2.079  -0.375 0.511  C11  TTG 17 
TTG C8   C8   C 0 1 Y N N 22.247 -4.431  28.513 0.947  -0.331 1.504  C8   TTG 18 
TTG N10  N10  N 0 1 Y N N 19.759 -4.469  28.346 -1.417 -0.172 1.367  N10  TTG 19 
TTG C7   C7   C 0 1 Y N N 22.263 -5.829  28.446 0.909  -0.369 2.863  C7   TTG 20 
TTG C5   C5   C 0 1 Y N N 19.810 -5.784  28.283 -1.517 -0.206 2.696  C5   TTG 21 
TTG C6   C6   C 0 1 Y N N 21.054 -6.537  28.321 -0.348 -0.306 3.495  C6   TTG 22 
TTG C4   C4   C 0 1 Y N N 18.618 -6.468  28.073 -2.774 -0.143 3.328  C4   TTG 23 
TTG C1   C1   C 0 1 Y N N 21.015 -7.946  28.156 -0.463 -0.340 4.892  C1   TTG 24 
TTG C3   C3   C 0 1 Y N N 18.619 -7.825  27.813 -2.852 -0.179 4.684  C3   TTG 25 
TTG C2   C2   C 0 1 Y N N 19.782 -8.563  27.878 -1.699 -0.277 5.470  C2   TTG 26 
TTG C27  C27  C 0 1 N N N 22.239 -8.908  28.259 0.770  -0.446 5.752  C27  TTG 27 
TTG N28  N28  N 0 1 N N N 22.788 -9.403  26.945 1.260  0.900  6.072  N28  TTG 28 
TTG C29  C29  C 0 1 N N N 23.612 -8.378  26.225 2.457  0.727  6.907  C29  TTG 29 
TTG C30  C30  C 0 1 N N N 23.478 -10.728 27.045 1.710  1.498  4.808  C30  TTG 30 
TTG O26  O26  O 0 1 N N N 19.693 -9.913  27.624 -1.811 -0.310 6.824  O26  TTG 31 
TTG O19  O19  O 0 1 N N N 23.995 1.910   27.423 1.205  -1.175 -5.393 O19  TTG 32 
TTG H251 1H25 H 0 0 N N N 20.213 2.345   29.703 -2.148 1.622  -3.526 H251 TTG 33 
TTG H252 2H25 H 0 0 N N N 18.806 2.820   28.819 -2.833 0.021  -3.156 H252 TTG 34 
TTG H311 1H31 H 0 0 N N N 19.117 0.095   30.239 -4.170 1.183  -4.891 H311 TTG 35 
TTG H312 2H31 H 0 0 N N N 18.075 1.409   30.915 -2.723 1.316  -5.918 H312 TTG 36 
TTG H313 3H31 H 0 0 N N N 17.710 0.570   29.355 -3.408 -0.284 -5.549 H313 TTG 37 
TTG H241 1H24 H 0 0 N N N 19.330 0.478   26.184 -1.598 -1.871 -4.072 H241 TTG 38 
TTG H171 1H17 H 0 0 N N N 19.431 -1.282  28.173 -1.767 -0.049 -1.678 H171 TTG 39 
TTG H22O OH22 H 0 0 N N N 21.297 4.330   26.854 0.428  2.613  -5.769 H22O TTG 40 
TTG H191 1H19 H 0 0 N N N 23.573 1.745   29.468 1.765  0.776  -5.012 H191 TTG 41 
TTG H192 2H19 H 0 0 N N N 22.328 2.469   28.562 2.917  -0.470 -4.477 H192 TTG 42 
TTG H111 1H11 H 0 0 N N N 24.128 -3.576  29.373 2.630  -1.310 0.615  H111 TTG 43 
TTG H112 2H11 H 0 0 N N N 24.172 -3.607  27.724 2.747  0.471  0.667  H112 TTG 44 
TTG H71  1H7  H 0 1 N N N 23.223 -6.370  28.492 1.818  -0.446 3.441  H71  TTG 45 
TTG H41  1H4  H 0 1 N N N 17.658 -5.926  28.113 -3.674 -0.066 2.735  H41  TTG 46 
TTG H31  1H3  H 0 1 N N N 17.674 -8.328  27.549 -3.819 -0.131 5.162  H31  TTG 47 
TTG H271 1H27 H 0 0 N N N 21.991 -9.772  28.919 0.526  -0.973 6.674  H271 TTG 48 
TTG H272 2H27 H 0 0 N N N 23.051 -8.430  28.856 1.542  -0.995 5.213  H272 TTG 49 
TTG H291 1H29 H 0 0 N N N 24.431 -7.997  26.879 2.860  1.704  7.172  H291 TTG 50 
TTG H292 2H29 H 0 0 N N N 24.018 -8.744  25.253 2.191  0.184  7.814  H292 TTG 51 
TTG H293 3H29 H 0 0 N N N 23.036 -7.434  26.084 3.207  0.163  6.353  H293 TTG 52 
TTG H301 1H30 H 0 0 N N N 22.804 -11.490 27.503 2.085  2.504  4.995  H301 TTG 53 
TTG H302 2H30 H 0 0 N N N 23.884 -11.094 26.073 2.506  0.888  4.381  H302 TTG 54 
TTG H303 3H30 H 0 0 N N N 24.279 -10.698 27.820 0.874  1.545  4.111  H303 TTG 55 
TTG H261 1H26 H 0 0 N N N 18.860 -10.330 27.436 -1.774 0.605  7.130  H261 TTG 56 
TTG H19O OH19 H 0 0 N N N 24.427 2.752   27.503 1.650  -1.155 -6.252 H19O TTG 57 
# 
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 
TTG C25 C31  SING N N 1  
TTG C25 C21  SING N N 2  
TTG C25 H251 SING N N 3  
TTG C25 H252 SING N N 4  
TTG C31 H311 SING N N 5  
TTG C31 H312 SING N N 6  
TTG C31 H313 SING N N 7  
TTG C21 O24  SING N N 8  
TTG C21 C16  SING N N 9  
TTG C21 C20  SING N N 10 
TTG O24 H241 SING N N 11 
TTG C16 C15  DOUB Y N 12 
TTG C16 C17  SING Y N 13 
TTG C20 O23  DOUB N N 14 
TTG C20 O22  SING N N 15 
TTG C15 C14  SING Y N 16 
TTG C15 C19  SING N N 17 
TTG C17 C13  DOUB Y N 18 
TTG C17 H171 SING N N 19 
TTG O22 H22O SING N N 20 
TTG C14 O18  DOUB N N 21 
TTG C14 N12  SING Y N 22 
TTG C19 O19  SING N N 23 
TTG C19 H191 SING N N 24 
TTG C19 H192 SING N N 25 
TTG C13 N12  SING Y N 26 
TTG C13 C9   SING N N 27 
TTG N12 C11  SING N N 28 
TTG C9  C8   DOUB Y N 29 
TTG C9  N10  SING Y N 30 
TTG C11 C8   SING N N 31 
TTG C11 H111 SING N N 32 
TTG C11 H112 SING N N 33 
TTG C8  C7   SING Y N 34 
TTG N10 C5   DOUB Y N 35 
TTG C7  C6   DOUB Y N 36 
TTG C7  H71  SING N N 37 
TTG C5  C6   SING Y N 38 
TTG C5  C4   SING Y N 39 
TTG C6  C1   SING Y N 40 
TTG C4  C3   DOUB Y N 41 
TTG C4  H41  SING N N 42 
TTG C1  C2   DOUB Y N 43 
TTG C1  C27  SING N N 44 
TTG C3  C2   SING Y N 45 
TTG C3  H31  SING N N 46 
TTG C2  O26  SING N N 47 
TTG C27 N28  SING N N 48 
TTG C27 H271 SING N N 49 
TTG C27 H272 SING N N 50 
TTG N28 C29  SING N N 51 
TTG N28 C30  SING N N 52 
TTG C29 H291 SING N N 53 
TTG C29 H292 SING N N 54 
TTG C29 H293 SING N N 55 
TTG C30 H301 SING N N 56 
TTG C30 H302 SING N N 57 
TTG C30 H303 SING N N 58 
TTG O26 H261 SING N N 59 
TTG O19 H19O 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 
TTG SMILES           ACDLabs              10.04 O=C(O)C(O)(C=4C=C3c2nc1ccc(O)c(c1cc2CN3C(=O)C=4CO)CN(C)C)CC                                                                                                                      
TTG InChI            InChI                1.02b InChI=1/C23H25N3O6/c1-4-23(32,22(30)31)16-8-18-20-12(9-26(18)21(29)15(16)11-27)7-13-14(10-25(2)3)19(28)6-5-17(13)24-20/h5-8,27-28,32H,4,9-11H2,1-3H3,(H,30,31)/t23-/m0/s1/f/h30H 
TTG InChIKey         InChI                1.02b DPQJTQJZJNYUEC-NHPKAQBRDB                                                                                                                                                        
TTG SMILES_CANONICAL CACTVS               3.341 CC[C@@](O)(C(O)=O)C1=C(CO)C(=O)N2Cc3cc4c(CN(C)C)c(O)ccc4nc3C2=C1                                                                                                                 
TTG SMILES           CACTVS               3.341 CC[C](O)(C(O)=O)C1=C(CO)C(=O)N2Cc3cc4c(CN(C)C)c(O)ccc4nc3C2=C1                                                                                                                   
TTG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@](C1=C(C(=O)N2Cc3cc4c(ccc(c4CN(C)C)O)nc3C2=C1)CO)(C(=O)O)O                                                                                                                  
TTG SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C1=C(C(=O)N2Cc3cc4c(ccc(c4CN(C)C)O)nc3C2=C1)CO)(C(=O)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 
TTG "SYSTEMATIC NAME" ACDLabs              10.04 "(2S)-2-{1-[(dimethylamino)methyl]-2-hydroxy-8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl}-2-hydroxybutanoic acid" 
TTG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[1-(dimethylaminomethyl)-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxy-butanoic acid"          
# 
