data_COK
# 
_chem_comp.id                                    COK 
_chem_comp.name                                  
"[(2R,3S,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-4-HYDROXY-3-(PHOSPHONOOXY)TETRAHYDROFURAN-2-YL]METHYL (3R)-3-HYDROXY-4-{[3-({2-[(2-HYDROXYETHYL)DITHIO]ETHYL}AMINO)-3-OXOPROPYL]AMINO}-2,2-DIMETHYL-4-OXOBUTYL DIHYDROGEN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAC 
_chem_comp.formula                               "C23 H40 N7 O17 P3 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "S-(THIOETHYLHYDROXY)COENZYME A" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-03-22 
_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                        843.652 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     COK 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2GES 
_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 
COK N6A    AN6  N 0 1 N N N 37.568 38.917 -7.766 -2.565 7.283  2.044  N6A    COK 1  
COK C6A    AC6  C 0 1 Y N N 38.357 37.854 -7.916 -3.671 6.459  1.928  C6A    COK 2  
COK N1A    AN1  N 0 1 Y N N 37.962 36.816 -8.665 -4.893 6.922  2.171  N1A    COK 3  
COK C2A    AC2  C 0 1 Y N N 38.730 35.747 -8.822 -5.953 6.143  2.063  C2A    COK 4  
COK N3A    AN3  N 0 1 Y N N 39.916 35.670 -8.244 -5.867 4.877  1.712  N3A    COK 5  
COK C4A    AC4  C 0 1 Y N N 40.376 36.670 -7.481 -4.688 4.327  1.443  C4A    COK 6  
COK C5A    AC5  C 0 1 Y N N 39.597 37.808 -7.294 -3.528 5.113  1.549  C5A    COK 7  
COK N7A    AN7  N 0 1 Y N N 40.273 38.628 -6.495 -2.477 4.319  1.233  N7A    COK 8  
COK C8A    AC8  C 0 1 Y N N 41.426 38.038 -6.190 -2.907 3.124  0.950  C8A    COK 9  
COK N9A    AN9  N 0 1 Y N N 41.495 36.848 -6.784 -4.264 3.077  1.069  N9A    COK 10 
COK C1B    AC1* C 0 1 N N R 42.591 35.859 -6.656 -5.115 1.908  0.834  C1B    COK 11 
COK O4B    AO4* O 0 1 N N N 42.701 35.348 -5.315 -4.358 0.688  0.992  O4B    COK 12 
COK C2B    AC2* C 0 1 N N R 43.981 36.413 -6.967 -5.580 1.855  -0.643 C2B    COK 13 
COK O2B    AO2* O 0 1 N N N 44.157 36.527 -8.382 -6.764 2.633  -0.833 O2B    COK 14 
COK C3B    AC3* C 0 1 N N S 44.807 35.262 -6.398 -5.874 0.344  -0.838 C3B    COK 15 
COK O3B    AO3* O 0 1 N N N 44.722 34.133 -7.271 -7.271 0.083  -0.688 O3B    COK 16 
COK P3B    AP3* P 0 1 N N N 46.050 33.569 -7.981 -7.771 -0.583 -2.066 P3B    COK 17 
COK O8A    AO8  O 0 1 N N N 45.536 32.371 -8.925 -9.312 -1.025 -1.921 O8A    COK 18 
COK O9A    AO9  O 0 1 N N N 46.946 32.897 -6.826 -7.630 0.486  -3.261 O9A    COK 19 
COK O7A    AO7  O 0 1 N N N 46.772 34.624 -8.727 -6.943 -1.772 -2.367 O7A    COK 20 
COK C4B    AC4* C 0 1 N N R 44.079 34.998 -5.079 -5.067 -0.341 0.282  C4B    COK 21 
COK C5B    AC5* C 0 1 N N N 44.619 35.903 -3.969 -4.073 -1.332 -0.326 C5B    COK 22 
COK O5B    AO5* O 0 1 N N N 44.619 37.280 -4.357 -3.407 -2.041 0.721  O5B    COK 23 
COK P1A    AP1  P 0 1 N N S 45.314 38.384 -3.412 -2.382 -3.061 0.013  P1A    COK 24 
COK O1A    AO1  O 0 1 N N N 45.764 39.499 -4.275 -3.209 -4.156 -0.828 O1A    COK 25 
COK O2A    AO2  O 0 1 N N N 46.335 37.700 -2.583 -1.489 -2.311 -0.898 O2A    COK 26 
COK O3A    AO3  O 0 1 N N N 44.094 38.872 -2.475 -1.500 -3.802 1.138  O3A    COK 27 
COK P2A    AP2  P 0 1 N N R 43.805 38.246 -1.015 -0.187 -4.371 0.400  P2A    COK 28 
COK O4A    AO4  O 0 1 N N N 44.979 38.440 -0.134 -0.578 -5.671 -0.465 O4A    COK 29 
COK O5A    AO5  O 0 1 N N N 43.301 36.865 -1.196 0.366  -3.330 -0.495 O5A    COK 30 
COK O6A    AO6  O 0 1 N N N 42.613 39.196 -0.493 0.916  -4.772 1.502  O6A    COK 31 
COK CCP    PC12 C 0 1 N N N 41.258 38.842 -0.787 2.093  -5.155 0.788  CCP    COK 32 
COK CBP    PC11 C 0 1 N N N 40.290 40.024 -0.692 3.187  -5.551 1.782  CBP    COK 33 
COK CDP    PC13 C 0 1 N N N 40.332 40.596 0.728  3.506  -4.361 2.689  CDP    COK 34 
COK CEP    PC14 C 0 1 N N N 38.881 39.503 -0.988 2.702  -6.726 2.633  CEP    COK 35 
COK CAP    PC10 C 0 1 N N R 40.689 41.117 -1.692 4.447  -5.961 1.017  CAP    COK 36 
COK OAP    PO10 O 0 1 N N N 41.023 40.528 -2.951 4.184  -7.149 0.267  OAP    COK 37 
COK C9P    PC9  C 0 1 N N N 39.558 42.134 -1.889 4.848  -4.853 0.078  C9P    COK 38 
COK O9P    PO9  O 0 1 N N N 38.650 41.911 -2.688 4.661  -4.971 -1.115 O9P    COK 39 
COK N8P    PN8  N 0 1 N N N 39.644 43.242 -1.158 5.414  -3.730 0.563  N8P    COK 40 
COK C7P    PC7  C 0 1 N N N 38.620 44.297 -1.223 5.828  -2.663 -0.352 C7P    COK 41 
COK C6P    PC6  C 0 1 N N N 39.111 45.513 -2.011 6.436  -1.511 0.449  C6P    COK 42 
COK C5P    PC5  C 0 1 N N N 39.295 45.211 -3.500 6.862  -0.414 -0.492 C5P    COK 43 
COK O5P    PO5  O 0 1 N N N 40.404 44.926 -3.951 6.695  -0.542 -1.687 O5P    COK 44 
COK N4P    PN4  N 0 1 N N N 38.188 45.284 -4.234 7.428  0.709  -0.007 N4P    COK 45 
COK C3P    PC3  C 0 1 N N N 38.192 45.040 -5.684 7.842  1.775  -0.922 C3P    COK 46 
COK C2P    PC2  C 0 1 N N N 37.717 43.621 -6.002 8.450  2.928  -0.121 C2P    COK 47 
COK S1P    PS1  S 0 1 N N N 37.878 43.220 -7.781 8.963  4.248  -1.254 S1P    COK 48 
COK S49    S49  S 0 1 N N N 39.847 43.546 -8.155 7.127  4.931  -1.859 S49    COK 49 
COK C50    C50  C 0 1 N N N 40.854 42.044 -7.874 6.764  6.091  -0.513 C50    COK 50 
COK C51    C51  C 0 1 N N N 42.108 42.310 -7.039 7.693  7.302  -0.619 C51    COK 51 
COK O52    O52  O 0 1 N N N 41.734 42.800 -5.748 7.407  8.217  0.441  O52    COK 52 
COK HN61   1HN6 H 0 0 N N N 38.029 39.728 -8.128 -1.679 6.934  1.863  HN61   COK 53 
COK HN62   2HN6 H 0 0 N N N 37.370 39.052 -6.795 -2.677 8.211  2.306  HN62   COK 54 
COK H2     H2   H 0 1 N N N 38.381 34.927 -9.432 -6.928 6.560  2.270  H2     COK 55 
COK H8     H8   H 0 1 N N N 42.191 38.461 -5.556 -2.281 2.292  0.664  H8     COK 56 
COK "H1'"  H1*  H 0 1 N N N 42.310 35.088 -7.389 -5.973 1.917  1.507  "H1'"  COK 57 
COK "H2'"  H2*  H 0 1 N N N 44.217 37.411 -6.569 -4.787 2.188  -1.313 "H2'"  COK 58 
COK H3     H3   H 0 1 N N N 43.307 36.552 -8.806 -6.538 3.545  -0.608 H3     COK 59 
COK "H3'"  H3*  H 0 1 N N N 45.880 35.470 -6.277 -5.528 0.011  -1.816 "H3'"  COK 60 
COK HO9    HO9  H 0 1 N N N 47.830 32.765 -7.147 -8.183 1.244  -3.026 HO9    COK 61 
COK HO7    HO7  H 0 1 N N N 46.927 35.367 -8.156 ?      ?      ?      HO7    COK 62 
COK "H4'"  H4*  H 0 1 N N N 44.211 33.952 -4.766 -5.742 -0.862 0.960  "H4'"  COK 63 
COK "H5'1" 1H5* H 0 0 N N N 45.657 35.606 -3.760 -3.339 -0.791 -0.923 "H5'1" COK 64 
COK "H5'2" 2H5* H 0 0 N N N 43.982 35.788 -3.079 -4.607 -2.040 -0.961 "H5'2" COK 65 
COK HO2    HO2  H 0 1 N N N 47.118 37.554 -3.101 ?      ?      ?      HO2    COK 66 
COK HO5    HO5  H 0 1 N N N 43.193 36.686 -2.123 ?      ?      ?      HO5    COK 67 
COK H121   1H12 H 0 0 N N N 40.943 38.099 -0.039 2.439  -4.318 0.181  H121   COK 68 
COK H122   2H12 H 0 0 N N N 41.220 38.448 -1.813 1.866  -6.003 0.141  H122   COK 69 
COK H131   1H13 H 0 0 N N N 39.444 41.223 0.897  4.371  -4.598 3.308  H131   COK 70 
COK H132   2H13 H 0 0 N N N 41.240 41.205 0.851  3.726  -3.486 2.077  H132   COK 71 
COK H133   3H13 H 0 0 N N N 40.342 39.771 1.456  2.648  -4.151 3.328  H133   COK 72 
COK H141   1H14 H 0 0 N N N 38.950 38.534 -1.503 1.770  -6.455 3.129  H141   COK 73 
COK H142   2H14 H 0 0 N N N 38.351 40.223 -1.629 2.534  -7.593 1.994  H142   COK 74 
COK H143   3H14 H 0 0 N N N 38.330 39.378 -0.044 3.456  -6.968 3.382  H143   COK 75 
COK H10    H10  H 0 1 N N N 41.563 41.645 -1.283 5.256  -6.149 1.723  H10    COK 76 
COK H1     H1   H 0 1 N N N 41.097 41.208 -3.610 3.464  -6.939 -0.344 H1     COK 77 
COK HN8    HN8  H 0 1 N N N 40.427 43.361 -0.547 5.547  -3.628 1.518  HN8    COK 78 
COK H71    1H7  H 0 1 N N N 38.393 44.620 -0.196 6.569  -3.052 -1.051 H71    COK 79 
COK H72    2H7  H 0 1 N N N 37.726 43.892 -1.719 4.961  -2.303 -0.906 H72    COK 80 
COK H61    1H6  H 0 1 N N N 40.090 45.804 -1.604 5.695  -1.123 1.148  H61    COK 81 
COK H62    2H6  H 0 1 N N N 38.369 46.318 -1.908 7.303  -1.871 1.003  H62    COK 82 
COK HN4    HN4  H 0 1 N N N 37.324 45.512 -3.785 7.561  0.811  0.948  HN4    COK 83 
COK H31    1H3  H 0 1 N N N 39.220 45.159 -6.057 8.583  1.387  -1.621 H31    COK 84 
COK H32    2H3  H 0 1 N N N 37.517 45.760 -6.170 6.975  2.135  -1.476 H32    COK 85 
COK H21    1H2  H 0 1 N N N 36.652 43.552 -5.734 7.709  3.316  0.578  H21    COK 86 
COK H22    2H2  H 0 1 N N N 38.327 42.910 -5.426 9.317  2.567  0.433  H22    COK 87 
COK H501   1H50 H 0 0 N N N 41.184 41.679 -8.858 5.727  6.421  -0.587 H501   COK 88 
COK H502   2H50 H 0 0 N N N 40.234 41.308 -7.341 6.920  5.597  0.446  H502   COK 89 
COK H511   1H51 H 0 0 N N N 42.731 43.061 -7.547 8.729  6.973  -0.545 H511   COK 90 
COK H512   2H51 H 0 0 N N N 42.675 41.375 -6.924 7.536  7.797  -1.578 H512   COK 91 
COK H52    H52  H 0 1 N N N 41.651 42.071 -5.144 8.012  8.963  0.338  H52    COK 92 
# 
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 
COK N6A C6A    SING N N 1  
COK N6A HN61   SING N N 2  
COK N6A HN62   SING N N 3  
COK C6A N1A    SING Y N 4  
COK C6A C5A    DOUB Y N 5  
COK N1A C2A    DOUB Y N 6  
COK C2A N3A    SING Y N 7  
COK C2A H2     SING N N 8  
COK N3A C4A    DOUB Y N 9  
COK C4A C5A    SING Y N 10 
COK C4A N9A    SING Y N 11 
COK C5A N7A    SING Y N 12 
COK N7A C8A    DOUB Y N 13 
COK C8A N9A    SING Y N 14 
COK C8A H8     SING N N 15 
COK N9A C1B    SING N N 16 
COK C1B O4B    SING N N 17 
COK C1B C2B    SING N N 18 
COK C1B "H1'"  SING N N 19 
COK O4B C4B    SING N N 20 
COK C2B O2B    SING N N 21 
COK C2B C3B    SING N N 22 
COK C2B "H2'"  SING N N 23 
COK O2B H3     SING N N 24 
COK C3B O3B    SING N N 25 
COK C3B C4B    SING N N 26 
COK C3B "H3'"  SING N N 27 
COK O3B P3B    SING N N 28 
COK P3B O8A    DOUB N N 29 
COK P3B O9A    SING N N 30 
COK P3B O7A    SING N N 31 
COK O9A HO9    SING N N 32 
COK O7A HO7    SING N N 33 
COK C4B C5B    SING N N 34 
COK C4B "H4'"  SING N N 35 
COK C5B O5B    SING N N 36 
COK C5B "H5'1" SING N N 37 
COK C5B "H5'2" SING N N 38 
COK O5B P1A    SING N N 39 
COK P1A O1A    DOUB N N 40 
COK P1A O2A    SING N N 41 
COK P1A O3A    SING N N 42 
COK O2A HO2    SING N N 43 
COK O3A P2A    SING N N 44 
COK P2A O4A    DOUB N N 45 
COK P2A O5A    SING N N 46 
COK P2A O6A    SING N N 47 
COK O5A HO5    SING N N 48 
COK O6A CCP    SING N N 49 
COK CCP CBP    SING N N 50 
COK CCP H121   SING N N 51 
COK CCP H122   SING N N 52 
COK CBP CDP    SING N N 53 
COK CBP CEP    SING N N 54 
COK CBP CAP    SING N N 55 
COK CDP H131   SING N N 56 
COK CDP H132   SING N N 57 
COK CDP H133   SING N N 58 
COK CEP H141   SING N N 59 
COK CEP H142   SING N N 60 
COK CEP H143   SING N N 61 
COK CAP OAP    SING N N 62 
COK CAP C9P    SING N N 63 
COK CAP H10    SING N N 64 
COK OAP H1     SING N N 65 
COK C9P O9P    DOUB N N 66 
COK C9P N8P    SING N N 67 
COK N8P C7P    SING N N 68 
COK N8P HN8    SING N N 69 
COK C7P C6P    SING N N 70 
COK C7P H71    SING N N 71 
COK C7P H72    SING N N 72 
COK C6P C5P    SING N N 73 
COK C6P H61    SING N N 74 
COK C6P H62    SING N N 75 
COK C5P O5P    DOUB N N 76 
COK C5P N4P    SING N N 77 
COK N4P C3P    SING N N 78 
COK N4P HN4    SING N N 79 
COK C3P C2P    SING N N 80 
COK C3P H31    SING N N 81 
COK C3P H32    SING N N 82 
COK C2P S1P    SING N N 83 
COK C2P H21    SING N N 84 
COK C2P H22    SING N N 85 
COK S1P S49    SING N N 86 
COK S49 C50    SING N N 87 
COK C50 C51    SING N N 88 
COK C50 H501   SING N N 89 
COK C50 H502   SING N N 90 
COK C51 O52    SING N N 91 
COK C51 H511   SING N N 92 
COK C51 H512   SING N N 93 
COK O52 H52    SING N N 94 
# 
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 
COK SMILES           ACDLabs              10.04 O=C(NCCSSCCO)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O 
COK InChI            InChI                1.02b 
;InChI=1/C23H40N7O17P3S2/c1-23(2,18(34)21(35)26-4-3-14(32)25-5-7-51-52-8-6-31)10-44-50(41,42)47-49(39,40)43-9-13-17(46-48(36,37)38)16(33)22(45-13)30-12-29-15-19(24)27-11-28-20(15)30/h11-13,16-18,22,31,33-34H,3-10H2,1-2H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1/f/h25-26,36-37,39,41H,24H2
;
COK InChIKey         InChI                1.02b MQCDRNSLNTXXSJ-XZFIVJFQDN 
COK 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)NCCSSCCO 
COK 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)NCCSSCCO 
COK 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)NCCSSCCO)O 
COK 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)NCCSSCCO)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 
COK "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-4-{[3-({2-[(2-hydroxyethyl)disulfanyl]ethyl}amino)-3-oxopropyl]amino}-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate (non-preferred name)" 
COK "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-4-[[3-[2-(2-hydroxyethyldisulfanyl)ethylamino]-3-oxo-propyl]amino]-2,2-dimethyl-4-oxo-butoxy]phosphoryl] hydrogen phosphate"                   
# 
