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                   2021-03-13
_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  Y  N   3  
323  C21  C20   SING  Y  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  N  N   8  
323  C23  C18   DOUB  Y  N   9  
323  C19  C18   SING  Y  N  10  
323  C24  O2    SING  N  N  11  
323  C18  C1    SING  N  N  12  
323  C10  C11   DOUB  Y  N  13  
323  C10  C2    SING  Y  N  14  
323  C1   C2    DOUB  N  N  15  
323  C1   C5    SING  N  N  16  
323  C11  C12   SING  Y  N  17  
323  C2   C3    SING  Y  N  18  
323  C9   C5    DOUB  Y  N  19  
323  C9   C8    SING  Y  N  20  
323  C5   C4    SING  Y  N  21  
323  C17  N1    SING  N  N  22  
323  C12  N1    DOUB  N  N  23  
323  C12  C13   SING  Y  N  24  
323  C8   C7    DOUB  Y  N  25  
323  C3   C13   DOUB  Y  N  26  
323  C3   O1    SING  N  N  27  
323  N1   C16   SING  N  N  28  
323  C4   O1    SING  N  N  29  
323  C4   C6    DOUB  Y  N  30  
323  C7   C6    SING  Y  N  31  
323  C7   N2    SING  N  N  32  
323  C15  N2    SING  N  N  33  
323  N2   C14   SING  N  N  34  
323  C10  H10   SING  N  N  35  
323  C11  H11   SING  N  N  36  
323  C13  H13   SING  N  N  37  
323  C14  H114  SING  N  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  N  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  N  N  47  
323  C17  H217  SING  N  N  48  
323  C17  H317  SING  N  N  49  
323  C19  H19   SING  N  N  50  
323  C20  H20   SING  N  N  51  
323  C22  H22   SING  N  N  52  
323  C25  H25   SING  N  N  53  
323  C6   H6    SING  N  N  54  
323  C8   H8    SING  N  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  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"  
323  InChI             InChI                 1.03   "InChI=1S/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                 1.03   ZFGLYCCNMJCDCP-UHFFFAOYSA-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
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
323  "Create component"      2008-06-30  RCSB  
323  "Modify aromatic_flag"  2011-06-04  RCSB  
323  "Modify descriptor"     2011-06-04  RCSB  
323  "Modify synonyms"       2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     323
_pdbx_chem_comp_synonyms.name        "5-Carboxy-N,N'-tetramethyl rhodamine"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
