data_COA
# 
_chem_comp.id                                    COA 
_chem_comp.name                                  "COENZYME A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAC 
_chem_comp.formula                               "C21 H36 N7 O16 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                    2008-12-05 
_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                        767.534 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     COA 
_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        1H16 
_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 
COA N1A  AN1  N 0 1 Y N N 88.604 -84.694 -15.401 5.319  1.844  -8.048 N1A  COA 1  
COA C2A  AC2  C 0 1 Y N N 88.517 -85.362 -16.614 4.099  1.802  -8.549 C2A  COA 2  
COA N3A  AN3  N 0 1 Y N N 88.453 -84.811 -17.827 3.050  1.465  -7.829 N3A  COA 3  
COA C4A  AC4  C 0 1 Y N N 88.489 -83.464 -17.791 3.184  1.143  -6.546 C4A  COA 4  
COA C5A  AC5  C 0 1 Y N N 88.578 -82.623 -16.644 4.463  1.177  -5.964 C5A  COA 5  
COA C6A  AC6  C 0 1 Y N N 88.637 -83.315 -15.345 5.551  1.543  -6.774 C6A  COA 6  
COA N6A  AN6  N 0 1 N N N 88.719 -82.694 -14.209 6.834  1.590  -6.258 N6A  COA 7  
COA N7A  AN7  N 0 1 Y N N 88.593 -81.311 -16.984 4.320  0.817  -4.666 N7A  COA 8  
COA C8A  AC8  C 0 1 Y N N 88.514 -81.293 -18.313 3.066  0.575  -4.419 C8A  COA 9  
COA N9A  AN9  N 0 1 Y N N 88.444 -82.569 -18.860 2.324  0.765  -5.547 N9A  COA 10 
COA C1B  AC1* C 0 1 N N R 88.283 -82.893 -20.305 0.874  0.592  -5.671 C1B  COA 11 
COA C2B  AC2* C 0 1 N N R 89.169 -84.003 -20.810 0.522  -0.887 -5.972 C2B  COA 12 
COA O2B  AO2* O 0 1 N N N 90.493 -83.537 -21.068 0.574  -1.148 -7.376 O2B  COA 13 
COA C3B  AC3* C 0 1 N N S 88.447 -84.352 -22.103 -0.933 -0.988 -5.445 C3B  COA 14 
COA O3B  AO3* O 0 1 N N N 88.534 -83.338 -23.020 -1.864 -0.846 -6.519 O3B  COA 15 
COA P3B  AP3* P 0 1 N N N 88.567 -83.763 -24.632 -2.756 -2.186 -6.542 P3B  COA 16 
COA O7A  AO7  O 0 1 N N N 89.776 -84.773 -24.812 -3.463 -2.331 -5.250 O7A  COA 17 
COA O8A  AO8  O 0 1 N N N 88.868 -82.454 -25.462 -3.833 -2.094 -7.735 O8A  COA 18 
COA O9A  AO9  O 0 1 N N N 87.187 -84.445 -25.005 -1.802 -3.462 -6.777 O9A  COA 19 
COA C4B  AC4* C 0 1 N N R 86.997 -84.491 -21.556 -1.055 0.188  -4.457 C4B  COA 20 
COA O4B  AO4* O 0 1 N N N 86.957 -83.461 -20.476 0.223  0.843  -4.407 O4B  COA 21 
COA C5B  AC5* C 0 1 N N N 86.578 -85.793 -20.934 -1.426 -0.335 -3.068 C5B  COA 22 
COA O5B  AO5* O 0 1 N N N 86.663 -86.765 -22.015 -1.530 0.760  -2.158 O5B  COA 23 
COA P1A  AP1  P 0 1 N N S 85.512 -87.899 -22.132 -1.921 0.140  -0.724 P1A  COA 24 
COA O1A  AO1  O 0 1 N N N 85.973 -88.842 -23.231 -0.866 -0.803 -0.292 O1A  COA 25 
COA O2A  AO2  O 0 1 N N N 84.135 -87.325 -22.276 -3.324 -0.640 -0.842 O2A  COA 26 
COA O3A  AO3  O 0 1 N N N 85.544 -88.672 -20.806 -2.055 1.326  0.355  O3A  COA 27 
COA P2A  AP2  P 0 1 N N S 86.526 -89.838 -20.232 -2.445 0.637  1.757  P2A  COA 28 
COA O4A  AO4  O 0 1 N N N 85.941 -91.222 -20.387 -3.727 -0.087 1.611  O4A  COA 29 
COA O5A  AO5  O 0 1 N N N 87.913 -89.766 -20.815 -1.289 -0.397 2.186  O5A  COA 30 
COA O6A  AO6  O 0 1 N N N 86.631 -89.411 -18.674 -2.596 1.772  2.889  O6A  COA 31 
COA CBP  PC11 C 0 1 N N N 85.960 -88.636 -16.536 -3.101 2.128  5.225  CBP  COA 32 
COA CCP  PC12 C 0 1 N N N 85.521 -89.408 -17.812 -2.941 1.101  4.103  CCP  COA 33 
COA CDP  PC13 C 0 1 N N N 87.492 -88.790 -16.210 -1.784 2.884  5.416  CDP  COA 34 
COA CEP  PC14 C 0 1 N N N 85.602 -87.210 -16.950 -4.208 3.118  4.857  CEP  COA 35 
COA CAP  PC10 C 0 1 N N R 85.185 -89.137 -15.254 -3.470 1.410  6.525  CAP  COA 36 
COA OAP  PO10 O 0 1 N N N 85.502 -88.266 -14.128 -4.764 0.819  6.391  OAP  COA 37 
COA C9P  PC9  C 0 1 N N N 83.668 -89.166 -15.416 -2.453 0.335  6.811  C9P  COA 38 
COA O9P  PO9  O 0 1 N N N 83.089 -90.069 -16.224 -2.758 -0.832 6.699  O9P  COA 39 
COA N8P  PN8  N 0 1 N N N 82.996 -88.277 -14.719 -1.205 0.672  7.191  N8P  COA 40 
COA C7P  PC7  C 0 1 N N N 81.536 -88.193 -14.746 -0.240 -0.370 7.547  C7P  COA 41 
COA C6P  PC6  C 0 1 N N N 81.050 -88.284 -13.298 1.089  0.275  7.938  C6P  COA 42 
COA C5P  PC5  C 0 1 N N N 81.483 -89.572 -12.633 2.081  -0.797 8.305  C5P  COA 43 
COA O5P  PO5  O 0 1 N N N 81.508 -90.722 -13.248 1.756  -1.965 8.258  O5P  COA 44 
COA N4P  PN4  N 0 1 N N N 81.828 -89.421 -11.370 3.329  -0.460 8.685  N4P  COA 45 
COA C3P  PC3  C 0 1 N N N 82.305 -90.554 -10.461 4.294  -1.504 9.041  C3P  COA 46 
COA C2P  PC2  C 0 1 N N N 81.066 -91.302 -10.008 5.624  -0.857 9.432  C2P  COA 47 
COA S1P  PS1  S 0 1 N N N 81.437 -92.641 -8.819  6.818  -2.150 9.873  S1P  COA 48 
COA H2A  AH2  H 0 1 N N N 88.499 -86.423 -16.572 3.955  2.054  -9.590 H2A  COA 49 
COA H61A AH61 H 0 0 N N N 88.759 -83.212 -13.361 7.577  1.844  -6.827 H61A COA 50 
COA H62A AH62 H 0 0 N N N 88.742 -81.700 -14.186 6.990  1.368  -5.326 H62A COA 51 
COA H8A  AH8  H 0 1 N N N 88.505 -80.403 -18.891 2.670  0.269  -3.462 H8A  COA 52 
COA H1B  AH1* H 0 1 N N N 88.506 -81.957 -20.837 0.475  1.247  -6.445 H1B  COA 53 
COA H2B  AH2* H 0 1 N N N 89.304 -84.841 -20.111 1.182  -1.562 -5.427 H2B  COA 54 
COA HO2A AHO2 H 0 0 N N N 91.099 -84.311 -21.186 1.484  -0.978 -7.658 HO2A COA 55 
COA H3B  AH3* H 0 1 N N N 88.840 -85.231 -22.634 -1.087 -1.936 -4.930 H3B  COA 56 
COA HOA8 8HOA H 0 0 N N N 88.887 -82.696 -26.380 -4.345 -2.914 -7.713 HOA8 COA 57 
COA HOA9 9HOA H 0 0 N N N 87.287 -85.430 -24.978 -1.362 -3.328 -7.628 HOA9 COA 58 
COA H4B  AH4* H 0 1 N N N 86.314 -84.396 -22.413 -1.816 0.886  -4.805 H4B  COA 59 
COA H51A AH51 H 0 0 N N N 87.257 -86.066 -20.113 -0.655 -1.023 -2.721 H51A COA 60 
COA H52A AH52 H 0 0 N N N 85.568 -85.741 -20.501 -2.382 -0.857 -3.120 H52A COA 61 
COA HOA2 2HOA H 0 0 N N N 83.460 -87.990 -22.345 -3.982 0.008  -1.125 HOA2 COA 62 
COA HOA5 5HOA H 0 0 N N N 88.486 -90.446 -20.480 -0.473 0.114  2.270  HOA5 COA 63 
COA H121 1H12 H 0 0 N N N 84.670 -88.901 -18.289 -2.152 0.396  4.365  H121 COA 64 
COA H122 2H12 H 0 0 N N N 85.201 -90.432 -17.569 -3.879 0.563  3.967  H122 COA 65 
COA H131 1H13 H 0 0 N N N 87.750 -89.858 -16.155 -0.972 2.170  5.556  H131 COA 66 
COA H132 2H13 H 0 0 N N N 88.085 -88.310 -17.002 -1.584 3.494  4.535  H132 COA 67 
COA H133 3H13 H 0 0 N N N 87.711 -88.310 -15.245 -1.858 3.526  6.294  H133 COA 68 
COA H141 1H14 H 0 0 N N N 84.508 -87.101 -16.982 -5.159 2.590  4.787  H141 COA 69 
COA H142 2H14 H 0 0 N N N 86.020 -86.501 -16.221 -4.276 3.889  5.625  H142 COA 70 
COA H143 3H14 H 0 0 N N N 86.020 -87.002 -17.946 -3.978 3.580  3.897  H143 COA 71 
COA H10  H10  H 0 1 N N N 85.516 -90.172 -15.085 -3.481 2.127  7.346  H10  COA 72 
COA HO1  HO1  H 0 1 N N N 84.663 -87.945 -13.712 -4.710 0.192  5.656  HO1  COA 73 
COA HN8  HN8  H 0 1 N N N 83.501 -87.635 -14.150 -0.945 1.606  7.229  HN8  COA 74 
COA H71  1H7  H 0 1 N N N 81.222 -87.237 -15.189 -0.624 -0.948 8.388  H71  COA 75 
COA H72  2H7  H 0 1 N N N 81.110 -89.006 -15.352 -0.087 -1.030 6.693  H72  COA 76 
COA H61  1H6  H 0 1 N N N 81.462 -87.436 -12.731 1.473  0.853  7.098  H61  COA 77 
COA H62  2H6  H 0 1 N N N 79.950 -88.260 -13.307 0.935  0.935  8.793  H62  COA 78 
COA HN4  HN4  H 0 1 N N N 81.774 -88.507 -10.981 3.589  0.473  8.722  HN4  COA 79 
COA H31  1H3  H 0 1 N N N 82.973 -91.229 -11.016 3.910  -2.082 9.881  H31  COA 80 
COA H32  2H3  H 0 1 N N N 82.866 -90.161 -9.600  4.448  -2.163 8.187  H32  COA 81 
COA H21  1H2  H 0 1 N N N 80.380 -90.588 -9.529  6.008  -0.279 8.591  H21  COA 82 
COA H22  2H2  H 0 1 N N N 80.617 -91.767 -10.898 5.470  -0.198 10.286 H22  COA 83 
COA HS1  HS1  H 0 1 N N N 80.661 -93.110 -8.535  7.885  -1.388 10.175 HS1  COA 84 
# 
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 
COA N1A C2A  SING Y N 1  
COA N1A C6A  DOUB Y N 2  
COA C2A N3A  DOUB Y N 3  
COA C2A H2A  SING N N 4  
COA N3A C4A  SING Y N 5  
COA C4A C5A  DOUB Y N 6  
COA C4A N9A  SING Y N 7  
COA C5A C6A  SING Y N 8  
COA C5A N7A  SING Y N 9  
COA C6A N6A  SING N N 10 
COA N6A H61A SING N N 11 
COA N6A H62A SING N N 12 
COA N7A C8A  DOUB Y N 13 
COA C8A N9A  SING Y N 14 
COA C8A H8A  SING N N 15 
COA N9A C1B  SING N N 16 
COA C1B C2B  SING N N 17 
COA C1B O4B  SING N N 18 
COA C1B H1B  SING N N 19 
COA C2B O2B  SING N N 20 
COA C2B C3B  SING N N 21 
COA C2B H2B  SING N N 22 
COA O2B HO2A SING N N 23 
COA C3B O3B  SING N N 24 
COA C3B C4B  SING N N 25 
COA C3B H3B  SING N N 26 
COA O3B P3B  SING N N 27 
COA P3B O7A  DOUB N N 28 
COA P3B O8A  SING N N 29 
COA P3B O9A  SING N N 30 
COA O8A HOA8 SING N N 31 
COA O9A HOA9 SING N N 32 
COA C4B O4B  SING N N 33 
COA C4B C5B  SING N N 34 
COA C4B H4B  SING N N 35 
COA C5B O5B  SING N N 36 
COA C5B H51A SING N N 37 
COA C5B H52A SING N N 38 
COA O5B P1A  SING N N 39 
COA P1A O1A  DOUB N N 40 
COA P1A O2A  SING N N 41 
COA P1A O3A  SING N N 42 
COA O2A HOA2 SING N N 43 
COA O3A P2A  SING N N 44 
COA P2A O4A  DOUB N N 45 
COA P2A O5A  SING N N 46 
COA P2A O6A  SING N N 47 
COA O5A HOA5 SING N N 48 
COA O6A CCP  SING N N 49 
COA CBP CCP  SING N N 50 
COA CBP CDP  SING N N 51 
COA CBP CEP  SING N N 52 
COA CBP CAP  SING N N 53 
COA CCP H121 SING N N 54 
COA CCP H122 SING N N 55 
COA CDP H131 SING N N 56 
COA CDP H132 SING N N 57 
COA CDP H133 SING N N 58 
COA CEP H141 SING N N 59 
COA CEP H142 SING N N 60 
COA CEP H143 SING N N 61 
COA CAP OAP  SING N N 62 
COA CAP C9P  SING N N 63 
COA CAP H10  SING N N 64 
COA OAP HO1  SING N N 65 
COA C9P O9P  DOUB N N 66 
COA C9P N8P  SING N N 67 
COA N8P C7P  SING N N 68 
COA N8P HN8  SING N N 69 
COA C7P C6P  SING N N 70 
COA C7P H71  SING N N 71 
COA C7P H72  SING N N 72 
COA C6P C5P  SING N N 73 
COA C6P H61  SING N N 74 
COA C6P H62  SING N N 75 
COA C5P O5P  DOUB N N 76 
COA C5P N4P  SING N N 77 
COA N4P C3P  SING N N 78 
COA N4P HN4  SING N N 79 
COA C3P C2P  SING N N 80 
COA C3P H31  SING N N 81 
COA C3P H32  SING N N 82 
COA C2P S1P  SING N N 83 
COA C2P H21  SING N N 84 
COA C2P H22  SING N N 85 
COA S1P HS1  SING N N 86 
# 
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 
COA SMILES           ACDLabs              10.04 O=C(NCCS)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O 
COA InChI            InChI                1.02b 
;InChI=1/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1/f/h23-24,33-34,36,38H,22H2
;
COA InChIKey         InChI                1.02b RGJOEKWQDUBAIZ-AUAMJRQIDD 
COA 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)NCCS 
COA 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)NCCS 
COA 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)NCCS)O 
COA 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)NCCS)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 
COA "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl dihydrogen diphosphate (non-preferred name)" 
COA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methyl [hydroxy-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butoxy]phosphoryl] hydrogen phosphate"                   
# 
