data_OXK
# 
_chem_comp.id                                    OXK 
_chem_comp.name                                  "OXALYL-COENZYME A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H36 N7 O19 P3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-26 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        839.554 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OXK 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
OXK C8     C8     C 0 1 Y N N 81.438 -25.021 0.686  9.881  -4.603 4.433  C8     OXK 1  
OXK N9     N9     N 0 1 Y N N 82.726 -24.877 1.037  8.881  -3.811 3.933  N9     OXK 2  
OXK C4     C4     C 0 1 Y N N 82.946 -25.565 2.160  7.885  -3.786 4.869  C4     OXK 3  
OXK C5     C5     C 0 1 Y N N 81.754 -26.174 2.517  8.343  -4.580 5.908  C5     OXK 4  
OXK N7     N7     N 0 1 Y N N 80.833 -25.826 1.586  9.588  -5.083 5.624  N7     OXK 5  
OXK N3     N3     N 0 1 Y N N 84.060 -25.753 2.919  6.715  -3.134 4.800  N3     OXK 6  
OXK C2     C2     C 0 1 Y N N 84.008 -26.512 4.016  5.989  -3.348 5.920  C2     OXK 7  
OXK N1     N1     N 0 1 Y N N 82.871 -27.117 4.390  6.304  -4.092 7.007  N1     OXK 8  
OXK C6     C6     C 0 1 Y N N 81.731 -26.960 3.670  7.502  -4.724 7.008  C6     OXK 9  
OXK N6     N6     N 0 1 N N N 80.586 -27.572 4.059  7.886  -5.511 8.107  N6     OXK 10 
OXK "C1'"  "C1'"  C 0 1 N N R 83.785 -24.094 0.347  8.888  -3.126 2.639  "C1'"  OXK 11 
OXK "C2'"  "C2'"  C 0 1 N N R 83.791 -24.211 -1.181 8.222  -3.927 1.518  "C2'"  OXK 12 
OXK "O2'"  "O2'"  O 0 1 N N N 84.563 -25.307 -1.672 8.999  -3.804 0.328  "O2'"  OXK 13 
OXK "C3'"  "C3'"  C 0 1 N N S 84.381 -22.871 -1.559 6.876  -3.243 1.369  "C3'"  OXK 14 
OXK "O3'"  "O3'"  O 0 1 N N N 85.801 -22.879 -1.432 6.318  -3.376 0.079  "O3'"  OXK 15 
OXK "C4'"  "C4'"  C 0 1 N N R 83.852 -21.920 -0.493 7.209  -1.799 1.702  "C4'"  OXK 16 
OXK "O4'"  "O4'"  O 0 1 N N N 83.613 -22.712 0.663  8.185  -1.871 2.755  "O4'"  OXK 17 
OXK "C5'"  "C5'"  C 0 1 N N N 82.553 -21.215 -0.856 6.010  -0.993 2.166  "C5'"  OXK 18 
OXK "O5'"  "O5'"  O 0 1 N N N 81.583 -22.131 -1.361 6.427  0.329  2.461  "O5'"  OXK 19 
OXK P1     P1     P 0 1 N N R 80.535 -21.652 -2.485 5.658  1.186  3.597  P1     OXK 20 
OXK O11    O11    O 0 1 N N N 79.746 -22.860 -2.926 5.698  0.243  4.910  O11    OXK 21 
OXK O12    O12    O 0 1 N N N 79.803 -20.444 -1.956 6.197  2.571  3.812  O12    OXK 22 
OXK O6     O6     O 0 1 N N N 81.529 -21.219 -3.683 4.103  1.142  3.156  O6     OXK 23 
OXK P2     P2     P 0 1 N N R 81.837 -19.734 -4.256 2.773  1.676  3.903  P2     OXK 24 
OXK O21    O21    O 0 1 N N N 83.209 -19.755 -4.902 2.853  0.974  5.358  O21    OXK 25 
OXK O22    O22    O 0 1 N N N 81.500 -18.651 -3.253 1.490  1.445  3.158  O22    OXK 26 
OXK O7     O7     O 0 1 N N N 80.786 -19.689 -5.487 3.173  3.216  4.177  O7     OXK 27 
OXK CPB    CPB    C 0 1 N N N 80.738 -18.598 -6.410 2.278  4.020  4.938  CPB    OXK 28 
OXK CPA    CPA    C 0 1 N N N 79.302 -18.092 -6.468 2.823  5.460  5.099  CPA    OXK 29 
OXK CP7    CP7    C 0 1 N N R 78.876 -17.732 -5.034 4.201  5.462  5.827  CP7    OXK 30 
OXK CP9    CP9    C 0 1 N N N 79.220 -16.859 -7.363 3.008  6.083  3.695  CP9    OXK 31 
OXK CP8    CP8    C 0 1 N N N 78.413 -19.210 -7.013 1.796  6.324  5.858  CP8    OXK 32 
OXK OP3    OP3    O 0 1 N N N 79.743 -16.715 -4.483 4.670  6.801  5.963  OP3    OXK 33 
OXK CP6    CP6    C 0 1 N N N 77.463 -17.233 -4.991 4.168  4.871  7.235  CP6    OXK 34 
OXK OP2    OP2    O 0 1 N N N 76.509 -17.980 -5.213 3.884  5.544  8.224  OP2    OXK 35 
OXK NP2    NP2    N 0 1 N N N 77.349 -15.947 -4.680 4.462  3.517  7.255  NP2    OXK 36 
OXK CP5    CP5    C 0 1 N N N 76.125 -15.186 -4.546 4.467  2.731  8.467  CP5    OXK 37 
OXK CP4    CP4    C 0 1 N N N 76.580 -13.831 -4.035 5.856  2.754  9.090  CP4    OXK 38 
OXK CP3    CP3    C 0 1 N N N 75.427 -12.861 -4.040 6.920  2.201  8.159  CP3    OXK 39 
OXK OP1    OP1    O 0 1 N N N 74.521 -12.973 -4.848 6.674  1.782  7.031  OP1    OXK 40 
OXK NP1    NP1    N 0 1 N N N 75.486 -11.906 -3.111 8.177  2.231  8.745  NP1    OXK 41 
OXK CP2    CP2    C 0 1 N N N 74.533 -10.840 -2.858 9.367  1.760  8.073  CP2    OXK 42 
OXK CP1    CP1    C 0 1 N N N 75.048 -9.630  -3.622 9.644  0.283  8.320  CP1    OXK 43 
OXK S      S      S 0 1 N N N 76.580 -9.100  -2.954 9.921  -0.080 10.080 S      OXK 44 
OXK P3     P3     P 0 1 N N N 86.834 -23.026 -2.660 6.017  -4.863 -0.471 P3     OXK 45 
OXK O31    O31    O 0 1 N N N 86.441 -24.375 -3.232 5.225  -4.610 -1.858 O31    OXK 46 
OXK O32    O32    O 0 1 N N N 86.586 -21.848 -3.570 7.215  -5.761 -0.572 O32    OXK 47 
OXK O33    O33    O 0 1 N N N 88.174 -22.985 -1.963 4.858  -5.381 0.530  O33    OXK 48 
OXK CM1    CM1    C 0 1 N N N 76.514 -7.578  -3.785 10.276 -1.765 9.974  CM1    OXK 49 
OXK OM2    OM2    O 0 1 N N N 75.672 -7.362  -4.655 10.350 -2.509 9.020  OM2    OXK 50 
OXK OM3    OM3    O 0 1 N N N 77.396 -5.358  -3.872 10.836 -3.481 11.421 OM3    OXK 51 
OXK OM4    OM4    O 0 1 N N N 78.427 -6.801  -2.606 10.489 -1.393 12.316 OM4    OXK 52 
OXK CM2    CM2    C 0 1 N N N 77.509 -6.512  -3.401 10.524 -2.177 11.389 CM2    OXK 53 
OXK H8     H8     H 0 1 N N N 80.959 -24.557 -0.192 10.795 -4.792 3.886  H8     OXK 54 
OXK "H1'"  "H1'"  H 0 1 N N N 84.750 -24.519 0.710  9.942  -2.912 2.433  "H1'"  OXK 55 
OXK H2     H2     H 0 1 N N N 84.920 -26.641 4.623  5.022  -2.858 5.952  H2     OXK 56 
OXK H6N1   1H6N   H 0 0 N N N 80.243 -28.135 3.281  7.994  -6.501 7.990  H6N1   OXK 57 
OXK H6N2   2H6N   H 0 0 N N N 80.569 -28.147 4.902  7.956  -5.090 9.014  H6N2   OXK 58 
OXK "H2'"  "H2'"  H 0 1 N N N 82.787 -24.422 -1.618 8.130  -4.997 1.729  "H2'"  OXK 59 
OXK HA     HA     H 0 1 N N N 84.567 -25.379 -2.619 9.934  -3.771 0.595  HA     OXK 60 
OXK "H3'"  "H3'"  H 0 1 N N N 84.120 -22.601 -2.609 6.174  -3.651 2.106  "H3'"  OXK 61 
OXK "H4'"  "H4'"  H 0 1 N N N 84.609 -21.114 -0.353 7.665  -1.288 0.845  "H4'"  OXK 62 
OXK "H5'1" "1H5'" H 0 0 N N N 82.730 -20.375 -1.568 5.577  -1.435 3.069  "H5'1" OXK 63 
OXK "H5'2" "2H5'" H 0 0 N N N 82.152 -20.630 0.005  5.246  -0.956 1.384  "H5'2" OXK 64 
OXK H11    H11    H 0 1 N N N 79.128 -22.577 -3.589 6.516  0.216  5.450  H11    OXK 65 
OXK H21    H21    H 0 1 N N N 83.390 -18.885 -5.238 2.605  0.029  5.445  H21    OXK 66 
OXK HPB1   1HPB   H 0 0 N N N 81.142 -18.865 -7.414 1.314  4.021  4.419  HPB1   OXK 67 
OXK HPB2   2HPB   H 0 0 N N N 81.469 -17.793 -6.164 2.142  3.538  5.913  HPB2   OXK 68 
OXK HP7    HP7    H 0 1 N N N 78.953 -18.664 -4.427 4.941  4.920  5.225  HP7    OXK 69 
OXK HP91   1HP9   H 0 0 N N N 79.637 -17.051 -8.379 3.444  7.086  3.766  HP91   OXK 70 
OXK HP92   2HP9   H 0 0 N N N 79.932 -16.062 -7.043 2.053  6.179  3.166  HP92   OXK 71 
OXK HP93   3HP9   H 0 0 N N N 78.169 -16.489 -7.405 3.669  5.474  3.069  HP93   OXK 72 
OXK HP81   1HP8   H 0 0 N N N 78.510 -20.155 -6.430 0.872  6.447  5.282  HP81   OXK 73 
OXK HP82   2HP8   H 0 0 N N N 78.769 -19.599 -7.996 2.193  7.326  6.054  HP82   OXK 74 
OXK HP83   3HP8   H 0 0 N N N 77.362 -18.840 -7.055 1.519  5.873  6.816  HP83   OXK 75 
OXK HP3    HP3    H 0 1 N N N 79.480 -16.493 -3.598 4.201  7.182  6.721  HP3    OXK 76 
OXK HP2    HP2    H 0 1 N N N 78.262 -15.515 -4.535 4.657  3.035  6.383  HP2    OXK 77 
OXK HP51   1HP5   H 0 0 N N N 75.350 -15.676 -3.912 3.726  3.136  9.165  HP51   OXK 78 
OXK HP52   2HP5   H 0 0 N N N 75.512 -15.141 -5.476 4.168  1.703  8.234  HP52   OXK 79 
OXK HP41   1HP4   H 0 0 N N N 77.455 -13.442 -4.607 5.864  2.162  10.014 HP41   OXK 80 
OXK HP42   2HP4   H 0 0 N N N 77.060 -13.903 -3.031 6.132  3.782  9.357  HP42   OXK 81 
OXK HP1    HP1    H 0 1 N N N 76.331 -11.999 -2.547 8.265  2.600  9.687  HP1    OXK 82 
OXK HP21   1HP2   H 0 0 N N N 74.363 -10.643 -1.774 9.207  1.926  7.003  HP21   OXK 83 
OXK HP22   2HP2   H 0 0 N N N 73.482 -11.113 -3.112 10.204 2.392  8.388  HP22   OXK 84 
OXK HP11   1HP1   H 0 0 N N N 74.298 -8.805  -3.651 8.813  -0.334 7.964  HP11   OXK 85 
OXK HP12   2HP1   H 0 0 N N N 75.117 -9.827  -4.717 10.545 -0.015 7.774  HP12   OXK 86 
OXK H31    H31    H 0 1 N N N 87.050 -24.462 -3.956 4.987  -5.380 -2.416 H31    OXK 87 
OXK H33    H33    H 0 1 N N N 88.783 -23.072 -2.687 4.555  -6.312 0.465  H33    OXK 88 
OXK HM3    HM3    H 0 1 N N N 78.023 -4.686  -3.630 11.054 -3.789 12.327 HM3    OXK 89 
# 
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 
OXK C8    N9     SING Y N 1  
OXK N9    C4     SING Y N 2  
OXK C4    C5     SING Y N 3  
OXK C8    N7     DOUB Y N 4  
OXK C5    N7     SING Y N 5  
OXK C4    N3     DOUB Y N 6  
OXK N3    C2     SING Y N 7  
OXK C2    N1     DOUB Y N 8  
OXK C5    C6     DOUB Y N 9  
OXK N1    C6     SING Y N 10 
OXK C6    N6     SING N N 11 
OXK N9    "C1'"  SING N N 12 
OXK "C1'" "C2'"  SING N N 13 
OXK "C2'" "O2'"  SING N N 14 
OXK "C2'" "C3'"  SING N N 15 
OXK "C3'" "O3'"  SING N N 16 
OXK "C3'" "C4'"  SING N N 17 
OXK "C1'" "O4'"  SING N N 18 
OXK "C4'" "O4'"  SING N N 19 
OXK "C4'" "C5'"  SING N N 20 
OXK "C5'" "O5'"  SING N N 21 
OXK "O5'" P1     SING N N 22 
OXK P1    O11    SING N N 23 
OXK P1    O12    DOUB N N 24 
OXK P1    O6     SING N N 25 
OXK O6    P2     SING N N 26 
OXK P2    O21    SING N N 27 
OXK P2    O22    DOUB N N 28 
OXK P2    O7     SING N N 29 
OXK O7    CPB    SING N N 30 
OXK CPB   CPA    SING N N 31 
OXK CPA   CP7    SING N N 32 
OXK CPA   CP9    SING N N 33 
OXK CPA   CP8    SING N N 34 
OXK CP7   OP3    SING N N 35 
OXK CP7   CP6    SING N N 36 
OXK CP6   OP2    DOUB N N 37 
OXK CP6   NP2    SING N N 38 
OXK NP2   CP5    SING N N 39 
OXK CP5   CP4    SING N N 40 
OXK CP4   CP3    SING N N 41 
OXK CP3   OP1    DOUB N N 42 
OXK CP3   NP1    SING N N 43 
OXK NP1   CP2    SING N N 44 
OXK CP2   CP1    SING N N 45 
OXK CP1   S      SING N N 46 
OXK "O3'" P3     SING N N 47 
OXK P3    O31    SING N N 48 
OXK P3    O32    DOUB N N 49 
OXK P3    O33    SING N N 50 
OXK S     CM1    SING N N 51 
OXK CM1   OM2    DOUB N N 52 
OXK CM1   CM2    SING N N 53 
OXK OM3   CM2    SING N N 54 
OXK OM4   CM2    DOUB N N 55 
OXK C8    H8     SING N N 56 
OXK "C1'" "H1'"  SING N N 57 
OXK C2    H2     SING N N 58 
OXK N6    H6N1   SING N N 59 
OXK N6    H6N2   SING N N 60 
OXK "C2'" "H2'"  SING N N 61 
OXK "O2'" HA     SING N N 62 
OXK "C3'" "H3'"  SING N N 63 
OXK "C4'" "H4'"  SING N N 64 
OXK "C5'" "H5'1" SING N N 65 
OXK "C5'" "H5'2" SING N N 66 
OXK O11   H11    SING N N 67 
OXK O21   H21    SING N N 68 
OXK CPB   HPB1   SING N N 69 
OXK CPB   HPB2   SING N N 70 
OXK CP7   HP7    SING N N 71 
OXK CP9   HP91   SING N N 72 
OXK CP9   HP92   SING N N 73 
OXK CP9   HP93   SING N N 74 
OXK CP8   HP81   SING N N 75 
OXK CP8   HP82   SING N N 76 
OXK CP8   HP83   SING N N 77 
OXK OP3   HP3    SING N N 78 
OXK NP2   HP2    SING N N 79 
OXK CP5   HP51   SING N N 80 
OXK CP5   HP52   SING N N 81 
OXK CP4   HP41   SING N N 82 
OXK CP4   HP42   SING N N 83 
OXK NP1   HP1    SING N N 84 
OXK CP2   HP21   SING N N 85 
OXK CP2   HP22   SING N N 86 
OXK CP1   HP11   SING N N 87 
OXK CP1   HP12   SING N N 88 
OXK O31   H31    SING N N 89 
OXK O33   H33    SING N N 90 
OXK OM3   HM3    SING N N 91 
# 
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 
OXK SMILES           ACDLabs              10.04 O=C(O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O 
OXK InChI            InChI                1.02b 
;InChI=1/C23H36N7O19P3S/c1-23(2,16(33)19(34)26-4-3-12(31)25-5-6-53-22(37)21(35)36)8-46-52(43,44)49-51(41,42)45-7-11-15(48-50(38,39)40)14(32)20(47-11)30-10-29-13-17(24)27-9-28-18(13)30/h9-11,14-16,20,32-33H,3-8H2,1-2H3,(H,25,31)(H,26,34)(H,35,36)(H,41,42)(H,43,44)(H2,24,27,28)(H2,38,39,40)/t11-,14-,15-,16+,20-/m1/s1/f/h25-26,35,38-39,41,43H,24H2
;
OXK InChIKey         InChI                1.02b QVXMZFTWJVBUHP-AJUPBUNUDQ 
OXK 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)NCCSC(=O)C(O)=O 
OXK 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)NCCSC(=O)C(O)=O 
OXK 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)NCCSC(=O)C(=O)O)O 
OXK 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)NCCSC(=O)C(=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 
OXK "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-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphaicosan-20-oic acid 3,5-dioxide (non-preferred name)" 
OXK "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]-2-oxo-ethanoic acid"            
# 
