data_323
# 
_chem_comp.id                                    323 
_chem_comp.name                                  2-[3,6-bis(dimethylamino)xanthen-9-yl]-5-methanoyl-benzoate 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H22 N2 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;5-Carboxy-N,N'-tetramethyl rhodamine
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-06-30 
_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                        414.453 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     323 
_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        3D1F 
_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 
323 C1   C1   C 0  1 N N N 48.094 96.682  122.501 0.004  -0.245 -0.844 C1   323 1  
323 O1   O1   O 0  1 N N N 47.916 96.158  125.382 -0.061 2.081  0.812  O1   323 2  
323 N1   N1   N 1  1 N N N 44.907 92.386  124.527 -4.775 2.615  0.242  N1   323 3  
323 C10  C10  C 0  1 Y N N 46.544 94.703  122.093 -2.453 0.100  -1.094 C10  323 4  
323 C11  C11  C 0  1 Y N N 45.780 93.673  122.564 -3.620 0.789  -0.835 C11  323 5  
323 C12  C12  C 0  1 Y N N 45.653 93.381  124.034 -3.595 1.915  -0.021 C12  323 6  
323 C13  C13  C 0  1 Y N N 46.469 94.344  124.946 -2.396 2.342  0.529  C13  323 7  
323 C14  C14  C 0  1 N N N 50.768 99.557  128.027 5.907  2.492  -0.328 C14  323 8  
323 C15  C15  C 0  1 N N N 51.769 101.028 126.242 4.521  4.058  1.109  C15  323 9  
323 C16  C16  C 0  1 N N N 44.783 92.107  125.991 -6.041 2.162  -0.340 C16  323 10 
323 C17  C17  C 0  1 N N N 44.139 91.477  123.649 -4.747 3.802  1.101  C17  323 11 
323 C18  C18  C 0  1 Y N N 48.202 96.978  120.996 0.038  -1.491 0.003  C18  323 12 
323 C19  C19  C 0  1 Y N N 47.039 97.593  120.434 0.019  -1.388 1.380  C19  323 13 
323 O2   O2   O -1 1 N N N 50.893 95.933  121.916 -0.951 -2.885 -2.704 O2   323 14 
323 N2   N2   N 0  1 N N N 50.895 99.873  126.599 4.617  2.874  0.251  N2   323 15 
323 C2   C2   C 0  1 Y N N 47.327 95.636  122.971 -1.254 0.524  -0.546 C2   323 16 
323 C20  C20  C 0  1 Y N N 47.028 97.910  119.051 0.049  -2.523 2.165  C20  323 17 
323 C21  C21  C 0  1 Y N N 48.148 97.634  118.222 0.098  -3.789 1.568  C21  323 18 
323 C22  C22  C 0  1 Y N N 49.309 97.019  118.798 0.116  -3.900 0.177  C22  323 19 
323 C23  C23  C 0  1 Y N N 49.365 96.675  120.190 0.081  -2.748 -0.608 C23  323 20 
323 C24  C24  C 0  1 N N N 50.659 96.031  120.641 0.100  -2.855 -2.079 C24  323 21 
323 C25  C25  C 0  1 N N N 48.092 97.989  116.793 0.135  -4.999 2.406  C25  323 22 
323 O3   O3   O 0  1 N N N 51.451 95.622  119.738 1.166  -2.914 -2.674 O3   323 23 
323 C3   C3   C 0  1 Y N N 47.221 95.356  124.445 -1.223 1.647  0.266  C3   323 24 
323 O4   O4   O 0  1 N N N 49.104 98.415  116.254 0.182  -6.094 1.887  O4   323 25 
323 C4   C4   C 0  1 Y N N 48.698 97.218  124.908 1.123  1.712  0.268  C4   323 26 
323 C5   C5   C 0  1 Y N N 48.816 97.517  123.519 1.218  0.592  -0.543 C5   323 27 
323 C6   C6   C 0  1 Y N N 49.377 97.993  125.900 2.256  2.471  0.533  C6   323 28 
323 C7   C7   C 0  1 Y N N 50.204 99.097  125.550 3.478  2.111  -0.015 C7   323 29 
323 C8   C8   C 0  1 Y N N 50.328 99.407  124.173 3.567  0.986  -0.826 C8   323 30 
323 C9   C9   C 0  1 Y N N 49.665 98.655  123.179 2.440  0.233  -1.087 C9   323 31 
323 H10  H10  H 0  1 N N N 46.587 94.855  121.025 -2.474 -0.775 -1.727 H10  323 32 
323 H11  H11  H 0  1 N N N 45.251 93.049  121.859 -4.552 0.454  -1.266 H11  323 33 
323 H13  H13  H 0  1 N N N 46.435 94.201  126.016 -2.374 3.217  1.162  H13  323 34 
323 H114 H114 H 0  0 N N N 50.736 98.466  128.160 6.672  3.201  -0.011 H114 323 35 
323 H214 H214 H 0  0 N N N 51.631 99.968  128.571 6.175  1.491  0.012  H214 323 36 
323 H314 H314 H 0  0 N N N 49.841 100.001 128.420 5.833  2.498  -1.416 H314 323 37 
323 H115 H115 H 0  0 N N N 51.984 101.618 127.145 4.300  4.933  0.497  H115 323 38 
323 H215 H215 H 0  0 N N N 52.712 100.656 125.814 3.725  3.914  1.839  H215 323 39 
323 H315 H315 H 0  0 N N N 51.256 101.661 125.504 5.468  4.208  1.628  H315 323 40 
323 H116 H116 H 0  0 N N N 44.753 91.020  126.156 -6.522 1.458  0.339  H116 323 41 
323 H216 H216 H 0  0 N N N 45.648 92.534  126.520 -6.695 3.020  -0.498 H216 323 42 
323 H316 H316 H 0  0 N N N 43.857 92.562  126.374 -5.847 1.672  -1.294 H316 323 43 
323 H117 H117 H 0  0 N N N 43.948 91.972  122.685 -4.907 3.504  2.138  H117 323 44 
323 H217 H217 H 0  0 N N N 44.716 90.556  123.480 -3.778 4.293  1.010  H217 323 45 
323 H317 H317 H 0  0 N N N 43.181 91.227  124.128 -5.534 4.490  0.795  H317 323 46 
323 H19  H19  H 0  1 N N N 46.182 97.813  121.053 -0.018 -0.414 1.846  H19  323 47 
323 H20  H20  H 0  1 N N N 46.151 98.370  118.620 0.035  -2.435 3.241  H20  323 48 
323 H22  H22  H 0  1 N N N 50.161 96.810  118.169 0.154  -4.874 -0.289 H22  323 49 
323 H25  H25  H 0  1 N N N 47.176 97.875  116.233 0.121  -4.911 3.482  H25  323 50 
323 H6   H6   H 0  1 N N N 49.259 97.734  126.942 2.184  3.344  1.165  H6   323 51 
323 H8   H8   H 0  1 N N N 50.946 100.241 123.876 4.517  0.702  -1.254 H8   323 52 
323 H9   H9   H 0  1 N N N 49.789 98.928  122.142 2.511  -0.640 -1.719 H9   323 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 
323 O4  C25  DOUB N N 1  
323 C25 C21  SING N N 2  
323 C21 C22  DOUB N N 3  
323 C21 C20  SING N N 4  
323 C22 C23  SING Y N 5  
323 C20 C19  DOUB Y N 6  
323 O3  C24  DOUB N N 7  
323 C23 C24  SING Y N 8  
323 C23 C18  DOUB N N 9  
323 C19 C18  SING N N 10 
323 C24 O2   SING Y N 11 
323 C18 C1   SING N N 12 
323 C10 C11  DOUB N N 13 
323 C10 C2   SING N N 14 
323 C1  C2   DOUB N N 15 
323 C1  C5   SING N N 16 
323 C11 C12  SING N N 17 
323 C2  C3   SING N N 18 
323 C9  C5   DOUB N N 19 
323 C9  C8   SING N N 20 
323 C5  C4   SING N N 21 
323 C17 N1   SING N N 22 
323 C12 N1   DOUB N N 23 
323 C12 C13  SING N N 24 
323 C8  C7   DOUB N N 25 
323 C3  C13  DOUB N N 26 
323 C3  O1   SING N N 27 
323 N1  C16  SING Y N 28 
323 C4  O1   SING N N 29 
323 C4  C6   DOUB N N 30 
323 C7  C6   SING Y N 31 
323 C7  N2   SING Y N 32 
323 C15 N2   SING N N 33 
323 N2  C14  SING Y N 34 
323 C10 H10  SING Y N 35 
323 C11 H11  SING N N 36 
323 C13 H13  SING N N 37 
323 C14 H114 SING Y N 38 
323 C14 H214 SING N N 39 
323 C14 H314 SING N N 40 
323 C15 H115 SING N N 41 
323 C15 H215 SING N N 42 
323 C15 H315 SING Y N 43 
323 C16 H116 SING N N 44 
323 C16 H216 SING N N 45 
323 C16 H316 SING N N 46 
323 C17 H117 SING Y N 47 
323 C17 H217 SING Y N 48 
323 C17 H317 SING N N 49 
323 C19 H19  SING Y N 50 
323 C20 H20  SING N N 51 
323 C22 H22  SING Y N 52 
323 C25 H25  SING N N 53 
323 C6  H6   SING Y N 54 
323 C8  H8   SING Y N 55 
323 C9  H9   SING N N 56 
# 
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 
323 SMILES           ACDLabs              10.04 [O-]C(=O)c4cc(C=O)ccc4C=1c3c(OC=2C=1C=C/C(=[N+](/C)C)C=2)cc(cc3)N(C)C                                                            
323 InChI            InChI                1.02b InChI=1/C25H22N2O4/c1-26(2)16-6-9-19-22(12-16)31-23-13-17(27(3)4)7-10-20(23)24(19)18-8-5-15(14-28)11-21(18)25(29)30/h5-14H,1-4H3 
323 InChIKey         InChI                1.02b ZFGLYCCNMJCDCP-UHFFFAOYAO                                                                                                        
323 SMILES_CANONICAL CACTVS               3.341 CN(C)c1ccc2c(OC3=CC(C=CC3=C2c4ccc(C=O)cc4C([O-])=O)=[N+](C)C)c1                                                                  
323 SMILES           CACTVS               3.341 CN(C)c1ccc2c(OC3=CC(C=CC3=C2c4ccc(C=O)cc4C([O-])=O)=[N+](C)C)c1                                                                  
323 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(C)c1ccc2c(c1)OC3=CC(=[N+](C)C)C=CC3=C2c4ccc(cc4C(=O)[O-])C=O                                                                  
323 SMILES           "OpenEye OEToolkits" 1.5.0 CN(C)c1ccc2c(c1)OC3=CC(=[N+](C)C)C=CC3=C2c4ccc(cc4C(=O)[O-])C=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 
323 "SYSTEMATIC NAME" ACDLabs              10.04 2-[6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl]-5-formylbenzoate      
323 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-(3-dimethylamino-6-dimethylazaniumylidene-xanthen-9-yl)-5-methanoyl-benzoate 
# 
