data_CMC
# 
_chem_comp.id                                    CMC 
_chem_comp.name                                  "CARBOXYMETHYL COENZYME *A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAC 
_chem_comp.formula                               "C23 H38 N7 O18 P3 S" 
_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                        825.570 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CMC 
_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        2CSC 
_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 
CMC N1A  AN1  N 0 1 Y N N 19.419 -7.993  13.211 6.464  2.144  -7.527 N1A  CMC 1  
CMC C2A  AC2  C 0 1 Y N N 19.053 -8.686  14.331 5.404  1.997  -8.300 C2A  CMC 2  
CMC N3A  AN3  N 0 1 Y N N 18.245 -9.715  14.370 4.239  1.596  -7.834 N3A  CMC 3  
CMC C4A  AC4  C 0 1 Y N N 17.884 -10.127 13.157 4.087  1.313  -6.544 C4A  CMC 4  
CMC C5A  AC5  C 0 1 Y N N 18.276 -9.604  11.925 5.185  1.459  -5.679 C5A  CMC 5  
CMC C6A  AC6  C 0 1 Y N N 19.105 -8.403  11.957 6.406  1.890  -6.224 C6A  CMC 6  
CMC N6A  AN6  N 0 1 N N N 19.654 -7.843  10.901 7.523  2.046  -5.421 N6A  CMC 7  
CMC N7A  AN7  N 0 1 Y N N 17.818 -10.338 10.883 4.763  1.117  -4.438 N7A  CMC 8  
CMC C8A  AC8  C 0 1 Y N N 17.153 -11.340 11.430 3.505  0.784  -4.484 C8A  CMC 9  
CMC N9A  AN9  N 0 1 Y N N 17.151 -11.263 12.834 3.042  0.892  -5.762 N9A  CMC 10 
CMC C1B  AC1* C 0 1 N N R 16.215 -11.985 13.756 1.679  0.605  -6.217 C1B  CMC 11 
CMC C2B  AC2* C 0 1 N N R 14.785 -11.788 13.329 1.513  -0.902 -6.534 C2B  CMC 12 
CMC O2B  AO2* O 0 1 N N N 14.385 -10.516 13.824 1.916  -1.189 -7.875 O2B  CMC 13 
CMC C3B  AC3* C 0 1 N N S 14.151 -12.893 14.150 -0.015 -1.104 -6.362 C3B  CMC 14 
CMC O3B  AO3* O 0 1 N N N 14.105 -12.523 15.469 -0.672 -1.058 -7.630 O3B  CMC 15 
CMC P3B  AP3* P 0 1 N N N 12.653 -12.939 16.213 -1.437 -2.463 -7.810 P3B  CMC 16 
CMC O7A  AO7  O 0 1 N N N 11.391 -12.205 15.552 -2.419 -2.633 -6.716 O7A  CMC 17 
CMC O8A  AO8  O 0 1 N N N 12.675 -12.437 17.733 -2.203 -2.480 -9.226 O8A  CMC 18 
CMC O9A  AO9  O 0 1 N N N 12.551 -14.527 16.082 -0.367 -3.666 -7.763 O9A  CMC 19 
CMC C4B  AC4* C 0 1 N N R 15.084 -14.074 13.827 -0.451 0.080  -5.477 C4B  CMC 20 
CMC O4B  AO4* O 0 1 N N N 16.396 -13.419 13.547 0.730  0.832  -5.153 O4B  CMC 21 
CMC C5B  AC5* C 0 1 N N N 14.782 -14.975 12.615 -1.104 -0.440 -4.196 C5B  CMC 22 
CMC O5B  AO5* O 0 1 N N N 14.471 -14.060 11.532 -1.498 0.663  -3.379 O5B  CMC 23 
CMC P1A  AP1  P 0 1 N N S 14.902 -14.343 10.008 -2.174 0.046  -2.055 P1A  CMC 24 
CMC O1A  AO1  O 0 1 N N N 14.088 -15.442 9.383  -1.189 -0.804 -1.349 O1A  CMC 25 
CMC O2A  AO2  O 0 1 N N N 16.414 -14.459 9.910  -3.451 -0.842 -2.469 O2A  CMC 26 
CMC O3A  AO3  O 0 1 N N N 14.415 -13.012 9.316  -2.644 1.241  -1.084 O3A  CMC 27 
CMC P2A  AP2  P 0 1 N N S 13.043 -12.554 8.558  -3.307 0.555  0.211  P2A  CMC 28 
CMC O4A  AO4  O 0 1 N N N 12.898 -13.305 7.235  -4.463 -0.269 -0.203 O4A  CMC 29 
CMC O5A  AO5  O 0 1 N N N 11.764 -12.685 9.394  -2.217 -0.378 0.941  O5A  CMC 30 
CMC O6A  AO6  O 0 1 N N N 13.378 -10.971 8.293  -3.802 1.699  1.230  O6A  CMC 31 
CMC CBP  PC11 C 0 1 N N N 14.731 -9.167  7.654  -4.872 2.065  3.366  CBP  CMC 32 
CMC CCP  PC12 C 0 1 N N N 14.328 -10.572 7.275  -4.378 1.030  2.354  CCP  CMC 33 
CMC CDP  PC13 C 0 1 N N N 15.393 -8.375  6.509  -3.694 2.924  3.832  CDP  CMC 34 
CMC CEP  PC14 C 0 1 N N N 13.380 -8.513  8.024  -5.926 2.959  2.709  CEP  CMC 35 
CMC CAP  PC10 C 0 1 N N R 15.682 -9.302  8.883  -5.488 1.349  4.569  CAP  CMC 36 
CMC OAP  PO10 O 0 1 N N N 16.916 -9.910  8.491  -6.669 0.657  4.158  OAP  CMC 37 
CMC C9P  PC9  C 0 1 N N N 15.982 -7.928  9.485  -4.496 0.362  5.129  C9P  CMC 38 
CMC O9P  PO9  O 0 1 N N N 15.111 -7.353  10.315 -4.684 -0.827 4.994  O9P  CMC 39 
CMC N8P  PN8  N 0 1 N N N 16.959 -7.261  8.905  -3.401 0.803  5.779  N8P  CMC 40 
CMC C7P  PC7  C 0 1 N N N 17.321 -5.915  9.332  -2.479 -0.155 6.393  C7P  CMC 41 
CMC C6P  PC6  C 0 1 N N N 16.583 -4.860  8.475  -1.328 0.600  7.061  C6P  CMC 42 
CMC C5P  PC5  C 0 1 N N N 17.173 -4.826  7.080  -0.379 -0.385 7.693  C5P  CMC 43 
CMC O5P  PO5  O 0 1 N N N 18.432 -4.778  6.874  -0.602 -1.575 7.616  O5P  CMC 44 
CMC N4P  PN4  N 0 1 N N N 16.294 -4.854  6.111  0.715  0.055  8.343  N4P  CMC 45 
CMC C3P  PC3  C 0 1 N N N 16.659 -4.834  4.625  1.637  -0.903 8.957  C3P  CMC 46 
CMC C2P  PC2  C 0 1 N N N 16.435 -6.217  3.979  2.788  -0.147 9.625  C2P  CMC 47 
CMC S1P  PS1  S 0 1 N N N 16.866 -6.367  2.242  3.930  -1.334 10.385 S1P  CMC 48 
CMC C1   C1   C 0 1 N N N 16.926 -4.777  1.429  5.155  -0.191 11.080 C1   CMC 49 
CMC C2   C2   C 0 1 N N N 15.714 -3.904  1.679  6.234  -0.976 11.781 C2   CMC 50 
CMC O21  O21  O 0 1 N N N 15.780 -2.589  1.691  6.181  -2.183 11.809 O21  CMC 51 
CMC O22  O22  O 0 1 N N N 14.662 -4.513  1.721  7.253  -0.335 12.374 O22  CMC 52 
CMC H2A  AH2  H 0 1 N N N 19.454 -8.381  15.312 5.494  2.215  -9.354 H2A  CMC 53 
CMC H61A AH61 H 0 0 N N N 19.417 -8.151  9.957  8.361  2.344  -5.809 H61A CMC 54 
CMC H62A AH62 H 0 0 N N N 20.667 -7.895  11.006 7.468  1.857  -4.472 H62A CMC 55 
CMC H8A  AH8  H 0 1 N N N 16.674 -12.118 10.811 2.916  0.469  -3.636 H8A  CMC 56 
CMC H1B  AH1* H 0 1 N N N 16.415 -11.618 14.789 1.431  1.210  -7.089 H1B  CMC 57 
CMC H2B  AH2* H 0 1 N N N 14.552 -11.819 12.239 2.069  -1.513 -5.824 H2B  CMC 58 
CMC HO2A AHO2 H 0 0 N N N 13.482 -10.391 13.554 2.852  -0.956 -7.941 HO2A CMC 59 
CMC H3B  AH3* H 0 1 N N N 13.087 -13.141 13.923 -0.221 -2.050 -5.861 H3B  CMC 60 
CMC HOA8 8HOA H 0 0 N N N 11.855 -12.671 18.152 -2.646 -3.336 -9.293 HOA8 CMC 61 
CMC HOA9 9HOA H 0 0 N N N 11.731 -14.761 16.501 0.251  -3.517 -8.491 HOA9 CMC 62 
CMC H4B  AH4* H 0 1 N N N 14.997 -14.774 14.690 -1.154 0.710  -6.022 H4B  CMC 63 
CMC H51A AH51 H 0 0 N N N 15.597 -15.696 12.375 -0.391 -1.059 -3.650 H51A CMC 64 
CMC H52A AH52 H 0 0 N N N 13.988 -15.735 12.804 -1.981 -1.035 -4.450 H52A CMC 65 
CMC HOA2 2HOA H 0 0 N N N 16.668 -14.626 9.010  -4.066 -0.252 -2.925 HOA2 CMC 66 
CMC HOA5 5HOA H 0 0 N N N 10.965 -12.418 8.953  -1.482 0.196  1.195  HOA5 CMC 67 
CMC H121 1H12 H 0 0 N N N 15.186 -11.273 7.156  -3.627 0.393  2.822  H121 CMC 68 
CMC H122 2H12 H 0 0 N N N 13.942 -10.667 6.233  -5.217 0.418  2.022  H122 CMC 69 
CMC H131 1H13 H 0 0 N N N 15.690 -7.337  6.788  -2.891 2.278  4.187  H131 CMC 70 
CMC H132 2H13 H 0 0 N N N 16.265 -8.935  6.098  -3.334 3.529  3.000  H132 CMC 71 
CMC H133 3H13 H 0 0 N N N 14.735 -8.364  5.608  -4.019 3.578  4.642  H133 CMC 72 
CMC H141 1H14 H 0 0 N N N 13.677 -7.475  8.303  -6.794 2.357  2.438  H141 CMC 73 
CMC H142 2H14 H 0 0 N N N 12.597 -8.577  7.232  -6.228 3.738  3.408  H142 CMC 74 
CMC H143 3H14 H 0 0 N N N 12.795 -9.057  8.801  -5.507 3.417  1.813  H143 CMC 75 
CMC H10  H10  H 0 1 N N N 15.171 -9.938  9.643  -5.745 2.081  5.335  H10  CMC 76 
CMC HO1  HO1  H 0 1 N N N 17.495 -9.992  9.239  -6.398 0.021  3.481  HO1  CMC 77 
CMC HN8  HN8  H 0 1 N N N 17.419 -7.769  8.150  -3.223 1.755  5.840  HN8  CMC 78 
CMC H71  1H7  H 0 1 N N N 17.142 -5.763  10.422 -3.011 -0.742 7.141  H71  CMC 79 
CMC H72  2H7  H 0 1 N N N 18.425 -5.759  9.322  -2.080 -0.818 5.626  H72  CMC 80 
CMC H61  1H6  H 0 1 N N N 15.481 -5.029  8.459  -0.796 1.188  6.313  H61  CMC 81 
CMC H62  2H6  H 0 1 N N N 16.585 -3.853  8.955  -1.726 1.264  7.828  H62  CMC 82 
CMC HN4  HN4  H 0 1 N N N 15.352 -4.890  6.502  0.893  1.006  8.404  HN4  CMC 83 
CMC H31  1H3  H 0 1 N N N 16.110 -4.031  4.078  1.106  -1.490 9.705  H31  CMC 84 
CMC H32  2H3  H 0 1 N N N 17.700 -4.469  4.462  2.036  -1.567 8.189  H32  CMC 85 
CMC H21  1H2  H 0 1 N N N 16.970 -6.997  4.567  3.320  0.440  8.876  H21  CMC 86 
CMC H22  2H2  H 0 1 N N N 15.377 -6.536  4.132  2.390  0.516  10.392 H22  CMC 87 
CMC H11  H11  H 0 1 N N N 17.860 -4.234  1.703  5.599  0.397  10.277 H11  CMC 88 
CMC H12  H12  H 0 1 N N N 17.094 -4.905  0.334  4.669  0.474  11.793 H12  CMC 89 
CMC HO22 2HO2 H 0 0 N N N 13.901 -3.965  1.877  7.945  -0.839 12.824 HO22 CMC 90 
# 
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 
CMC N1A C2A  SING Y N 1  
CMC N1A C6A  DOUB Y N 2  
CMC C2A N3A  DOUB Y N 3  
CMC C2A H2A  SING N N 4  
CMC N3A C4A  SING Y N 5  
CMC C4A C5A  DOUB Y N 6  
CMC C4A N9A  SING Y N 7  
CMC C5A C6A  SING Y N 8  
CMC C5A N7A  SING Y N 9  
CMC C6A N6A  SING N N 10 
CMC N6A H61A SING N N 11 
CMC N6A H62A SING N N 12 
CMC N7A C8A  DOUB Y N 13 
CMC C8A N9A  SING Y N 14 
CMC C8A H8A  SING N N 15 
CMC N9A C1B  SING N N 16 
CMC C1B C2B  SING N N 17 
CMC C1B O4B  SING N N 18 
CMC C1B H1B  SING N N 19 
CMC C2B O2B  SING N N 20 
CMC C2B C3B  SING N N 21 
CMC C2B H2B  SING N N 22 
CMC O2B HO2A SING N N 23 
CMC C3B O3B  SING N N 24 
CMC C3B C4B  SING N N 25 
CMC C3B H3B  SING N N 26 
CMC O3B P3B  SING N N 27 
CMC P3B O7A  DOUB N N 28 
CMC P3B O8A  SING N N 29 
CMC P3B O9A  SING N N 30 
CMC O8A HOA8 SING N N 31 
CMC O9A HOA9 SING N N 32 
CMC C4B O4B  SING N N 33 
CMC C4B C5B  SING N N 34 
CMC C4B H4B  SING N N 35 
CMC C5B O5B  SING N N 36 
CMC C5B H51A SING N N 37 
CMC C5B H52A SING N N 38 
CMC O5B P1A  SING N N 39 
CMC P1A O1A  DOUB N N 40 
CMC P1A O2A  SING N N 41 
CMC P1A O3A  SING N N 42 
CMC O2A HOA2 SING N N 43 
CMC O3A P2A  SING N N 44 
CMC P2A O4A  DOUB N N 45 
CMC P2A O5A  SING N N 46 
CMC P2A O6A  SING N N 47 
CMC O5A HOA5 SING N N 48 
CMC O6A CCP  SING N N 49 
CMC CBP CCP  SING N N 50 
CMC CBP CDP  SING N N 51 
CMC CBP CEP  SING N N 52 
CMC CBP CAP  SING N N 53 
CMC CCP H121 SING N N 54 
CMC CCP H122 SING N N 55 
CMC CDP H131 SING N N 56 
CMC CDP H132 SING N N 57 
CMC CDP H133 SING N N 58 
CMC CEP H141 SING N N 59 
CMC CEP H142 SING N N 60 
CMC CEP H143 SING N N 61 
CMC CAP OAP  SING N N 62 
CMC CAP C9P  SING N N 63 
CMC CAP H10  SING N N 64 
CMC OAP HO1  SING N N 65 
CMC C9P O9P  DOUB N N 66 
CMC C9P N8P  SING N N 67 
CMC N8P C7P  SING N N 68 
CMC N8P HN8  SING N N 69 
CMC C7P C6P  SING N N 70 
CMC C7P H71  SING N N 71 
CMC C7P H72  SING N N 72 
CMC C6P C5P  SING N N 73 
CMC C6P H61  SING N N 74 
CMC C6P H62  SING N N 75 
CMC C5P O5P  DOUB N N 76 
CMC C5P N4P  SING N N 77 
CMC N4P C3P  SING N N 78 
CMC N4P HN4  SING N N 79 
CMC C3P C2P  SING N N 80 
CMC C3P H31  SING N N 81 
CMC C3P H32  SING N N 82 
CMC C2P S1P  SING N N 83 
CMC C2P H21  SING N N 84 
CMC C2P H22  SING N N 85 
CMC S1P C1   SING N N 86 
CMC C1  C2   SING N N 87 
CMC C1  H11  SING N N 88 
CMC C1  H12  SING N N 89 
CMC C2  O21  DOUB N N 90 
CMC C2  O22  SING N N 91 
CMC O22 HO22 SING N N 92 
# 
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 
CMC SMILES           ACDLabs              10.04 O=C(O)CSCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O 
CMC InChI            InChI                1.02b 
;InChI=1/C23H38N7O18P3S/c1-23(2,18(35)21(36)26-4-3-13(31)25-5-6-52-8-14(32)33)9-45-51(42,43)48-50(40,41)44-7-12-17(47-49(37,38)39)16(34)22(46-12)30-11-29-15-19(24)27-10-28-20(15)30/h10-12,16-18,22,34-35H,3-9H2,1-2H3,(H,25,31)(H,26,36)(H,32,33)(H,40,41)(H,42,43)(H2,24,27,28)(H2,37,38,39)/t12-,16-,17-,18+,22-/m1/s1/f/h25-26,32,37-38,40,42H,24H2
;
CMC InChIKey         InChI                1.02b OBUOSIHPWVNVJN-SAXIPFBGDU 
CMC SMILES_CANONICAL CACTVS               3.341 CC(C)(CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[C@@H](O)C(=O)NCCC(=O)NCCSCC(O)=O 
CMC SMILES           CACTVS               3.341 CC(C)(CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[CH](O)C(=O)NCCC(=O)NCCSCC(O)=O 
CMC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)(CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSCC(=O)O)O 
CMC SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSCC(=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 
CMC "SYSTEMATIC NAME" ACDLabs              10.04 
"(3S,5S,9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-10,14-dioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphaicosan-20-oic acid 3,5-dioxide (non-preferred name)" 
CMC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"2-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethylsulfanyl]ethanoic acid"               
# 
