data_3HC
# 
_chem_comp.id                                    3HC 
_chem_comp.name                                  "3-HYDROXYBUTANOYL-COENZYME A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAC 
_chem_comp.formula                               "C25 H42 N7 O18 P3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "3-HYDROXYBUTYRYL-COENZYME A" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-05-31 
_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                        853.623 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     3HC 
_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        1F12 
_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 
3HC N1A  AN1  N 0 1 Y N N 30.286 34.211 40.550 4.912  1.421  -11.481 N1A  3HC 1  
3HC C2A  AC2  C 0 1 Y N N 29.022 34.036 41.166 3.919  2.283  -11.366 C2A  3HC 2  
3HC N3A  AN3  N 0 1 Y N N 29.012 34.147 42.578 2.956  2.138  -10.480 N3A  3HC 3  
3HC C4A  AC4  C 0 1 Y N N 30.201 34.380 43.324 2.945  1.095  -9.657  C4A  3HC 4  
3HC C5A  AC5  C 0 1 Y N N 31.452 34.504 42.696 3.984  0.151  -9.736  C5A  3HC 5  
3HC C6A  AC6  C 0 1 Y N N 31.481 34.439 41.286 4.989  0.350  -10.698 C6A  3HC 6  
3HC N6A  AN6  N 0 1 N N N 32.723 34.658 40.617 6.033  -0.548 -10.826 N6A  3HC 7  
3HC N7A  AN7  N 0 1 Y N N 32.454 34.743 43.644 3.739  -0.791 -8.795  N7A  3HC 8  
3HC C8A  AC8  C 0 1 Y N N 31.793 34.802 44.880 2.645  -0.491 -8.156  C8A  3HC 9  
3HC N9A  AN9  N 0 1 Y N N 30.407 34.600 44.705 2.120  0.665  -8.648  N9A  3HC 10 
3HC C1B  AC1* C 0 1 N N R 29.403 34.764 45.735 0.896  1.326  -8.189  C1B  3HC 11 
3HC C2B  AC2* C 0 1 N N R 28.329 33.648 45.796 -0.346 0.735  -8.902  C2B  3HC 12 
3HC O2B  AO2* O 0 1 N N N 27.255 33.673 44.849 -0.577 1.391  -10.151 O2B  3HC 13 
3HC C3B  AC3* C 0 1 N N S 27.923 33.571 47.277 -1.481 1.053  -7.893  C3B  3HC 14 
3HC O3B  AO3* O 0 1 N N N 26.680 34.097 47.764 -2.178 2.239  -8.281  O3B  3HC 15 
3HC P3B  AP3* P 0 1 N N N 26.091 33.403 49.061 -3.722 1.828  -8.479  P3B  3HC 16 
3HC O7A  AO7  O 0 1 N N N 26.063 31.928 48.985 -4.258 1.296  -7.206  O7A  3HC 17 
3HC O8A  AO8  O 0 1 N N N 26.848 33.779 50.278 -4.570 3.123  -8.919  O8A  3HC 18 
3HC O9A  AO9  O 0 1 N N N 24.717 33.933 49.188 -3.834 0.699  -9.621  O9A  3HC 19 
3HC C4B  AC4* C 0 1 N N R 29.129 34.177 48.004 -0.744 1.265  -6.556  C4B  3HC 20 
3HC O4B  AO4* O 0 1 N N N 29.921 34.941 47.072 0.654  1.037  -6.795  O4B  3HC 21 
3HC C5B  AC5* C 0 1 N N N 29.874 32.972 48.635 -1.262 0.272  -5.514  C5B  3HC 22 
3HC O5B  AO5* O 0 1 N N N 31.066 32.652 47.904 -0.568 0.471  -4.280  O5B  3HC 23 
3HC P1A  AP1  P 0 1 N N R 32.432 33.069 48.542 -1.160 -0.600 -3.235  P1A  3HC 24 
3HC O1A  AO1  O 0 1 N N N 32.836 32.059 49.530 -2.612 -0.372 -3.064  O1A  3HC 25 
3HC O2A  AO2  O 0 1 N N N 33.465 33.190 47.499 -0.913 -2.089 -3.796  O2A  3HC 26 
3HC O3A  AO3  O 0 1 N N N 32.143 34.442 49.251 -0.419 -0.432 -1.816  O3A  3HC 27 
3HC P2A  AP2  P 0 1 N N S 33.124 35.175 50.219 -1.057 -1.528 -0.825  P2A  3HC 28 
3HC O4A  AO4  O 0 1 N N N 32.370 35.724 51.359 -2.510 -1.286 -0.690  O4A  3HC 29 
3HC O5A  AO5  O 0 1 N N N 34.187 34.282 50.716 -0.812 -3.002 -1.426  O5A  3HC 30 
3HC O6A  AO6  O 0 1 N N N 33.786 36.327 49.395 -0.358 -1.416 0.621   O6A  3HC 31 
3HC CBP  PC11 C 0 1 N N N 34.122 37.997 47.634 -0.341 -2.355 2.847   CBP  3HC 32 
3HC CCP  PC12 C 0 1 N N N 33.251 36.833 48.163 -0.963 -2.409 1.450   CCP  3HC 33 
3HC CDP  PC13 C 0 1 N N N 33.200 38.922 46.812 -0.573 -0.971 3.456   CDP  3HC 34 
3HC CEP  PC14 C 0 1 N N N 35.213 37.430 46.698 1.162  -2.622 2.746   CEP  3HC 35 
3HC CAP  PC10 C 0 1 N N R 34.768 38.767 48.849 -0.989 -3.419 3.736   CAP  3HC 36 
3HC OAP  PO10 O 0 1 N N N 35.724 37.935 49.519 -0.873 -4.698 3.109   OAP  3HC 37 
3HC C9P  PC9  C 0 1 N N N 35.476 40.067 48.447 -0.293 -3.449 5.072   C9P  3HC 38 
3HC O9P  PO9  O 0 1 N N N 34.838 41.122 48.466 0.459  -4.360 5.343   O9P  3HC 39 
3HC N8P  PN8  N 0 1 N N N 36.882 40.081 48.463 -0.509 -2.464 5.966   N8P  3HC 40 
3HC C7P  PC7  C 0 1 N N N 37.603 41.238 48.167 0.182  -2.482 7.258   C7P  3HC 41 
3HC C6P  PC6  C 0 1 N N N 38.083 41.145 46.704 -0.235 -1.260 8.078   C6P  3HC 42 
3HC C5P  PC5  C 0 1 N N N 38.296 42.543 46.128 0.475  -1.280 9.406   C5P  3HC 43 
3HC O5P  PO5  O 0 1 N N N 38.762 43.435 46.849 1.240  -2.182 9.671   O5P  3HC 44 
3HC N4P  PN4  N 0 1 N N N 38.221 42.715 44.731 0.260  -0.294 10.300  N4P  3HC 45 
3HC C3P  PC3  C 0 1 N N N 38.703 43.876 44.120 0.951  -0.313 11.592  C3P  3HC 46 
3HC C2P  PC2  C 0 1 N N N 40.230 43.780 43.998 0.533  0.908  12.412  C2P  3HC 47 
3HC S1P  PS1  S 0 1 N N N 40.794 45.110 42.908 1.387  0.885  14.007  S1P  3HC 48 
3HC C1   C1   C 0 1 N N N 40.197 44.736 41.220 0.757  2.317  14.702  C1   3HC 49 
3HC O1   O1   O 0 1 N N N 39.616 43.673 40.990 -0.037 2.994  14.083  O1   3HC 50 
3HC C2   C2   C 0 1 N N N 40.511 45.700 40.071 1.190  2.738  16.083  C2   3HC 51 
3HC C3   C3   C 0 1 N N S 41.830 45.568 39.290 0.484  4.042  16.464  C3   3HC 52 
3HC O3   O3   O 0 1 N N N 42.065 46.373 38.403 -0.929 3.840  16.449  O3   3HC 53 
3HC C4   C4   C 0 1 N N N 42.977 44.673 39.832 0.924  4.469  17.866  C4   3HC 54 
3HC H2A  AH2  H 0 1 N N N 28.107 33.827 40.585 3.896  3.140  -12.023 H2A  3HC 55 
3HC H61A AH61 H 0 0 N N N 33.580 34.821 41.145 6.721  -0.400 -11.494 H61A 3HC 56 
3HC H62A AH62 H 0 0 N N N 32.599 35.431 39.964 6.078  -1.326 -10.249 H62A 3HC 57 
3HC H8A  AH8  H 0 1 N N N 32.290 34.981 45.848 2.217  -1.074 -7.353  H8A  3HC 58 
3HC H1B  AH1* H 0 1 N N N 28.923 35.712 45.397 0.957  2.402  -8.353  H1B  3HC 59 
3HC H2B  AH2* H 0 1 N N N 28.775 32.693 45.431 -0.239 -0.339 -9.043  H2B  3HC 60 
3HC HO2A AHO2 H 0 0 N N N 26.596 32.989 44.886 0.202  1.231  -10.698 HO2A 3HC 61 
3HC H3B  AH3* H 0 1 N N N 27.679 32.500 47.474 -2.172 0.213  -7.818  H3B  3HC 62 
3HC HOA8 8HOA H 0 0 N N N 26.494 33.362 51.055 -5.486 2.834  -9.026  HOA8 3HC 63 
3HC HOA9 9HOA H 0 0 N N N 24.363 33.516 49.965 -3.475 1.085  -10.432 HOA9 3HC 64 
3HC H4B  AH4* H 0 1 N N N 28.855 34.900 48.807 -0.899 2.285  -6.205  H4B  3HC 65 
3HC H51A AH51 H 0 0 N N N 30.091 33.146 49.714 -1.093 -0.745 -5.866  H51A 3HC 66 
3HC H52A AH52 H 0 0 N N N 29.205 32.085 48.734 -2.329 0.430  -5.360  H52A 3HC 67 
3HC HOA2 2HOA H 0 0 N N N 34.294 33.443 47.886 0.042  -2.196 -3.893  HOA2 3HC 68 
3HC HOA5 5HOA H 0 0 N N N 34.784 34.728 51.305 0.145  -3.119 -1.497  HOA5 3HC 69 
3HC H121 1H12 H 0 0 N N N 33.128 36.027 47.402 -0.798 -3.395 1.016   H121 3HC 70 
3HC H122 2H12 H 0 0 N N N 32.180 37.128 48.265 -2.034 -2.219 1.522   H122 3HC 71 
3HC H131 1H13 H 0 0 N N N 33.827 39.760 46.430 -1.637 -0.834 3.650   H131 3HC 72 
3HC H132 2H13 H 0 0 N N N 32.651 38.384 46.003 -0.020 -0.888 4.392   H132 3HC 73 
3HC H133 3H13 H 0 0 N N N 32.308 39.269 47.384 -0.228 -0.206 2.761   H133 3HC 74 
3HC H141 1H14 H 0 0 N N N 35.840 38.268 46.316 1.327  -3.608 2.312   H141 3HC 75 
3HC H142 2H14 H 0 0 N N N 35.821 36.635 47.189 1.623  -1.865 2.113   H142 3HC 76 
3HC H143 3H14 H 0 0 N N N 34.784 36.813 45.873 1.605  -2.584 3.741   H143 3HC 77 
3HC H10  H10  H 0 1 N N N 33.916 39.029 49.518 -2.042 -3.179 3.880   H10  3HC 78 
3HC HO1  HO1  H 0 1 N N N 36.113 38.398 50.251 0.072  -4.871 3.001   HO1  3HC 79 
3HC HN8  HN8  H 0 1 N N N 37.392 39.229 48.695 -1.121 -1.742 5.754   HN8  3HC 80 
3HC H71  1H7  H 0 1 N N N 37.024 42.169 48.371 1.259  -2.458 7.093   H71  3HC 81 
3HC H72  2H7  H 0 1 N N N 38.438 41.419 48.883 -0.082 -3.391 7.798   H72  3HC 82 
3HC H61  1H6  H 0 1 N N N 38.994 40.510 46.604 -1.313 -1.284 8.242   H61  3HC 83 
3HC H62  2H6  H 0 1 N N N 37.390 40.537 46.076 0.029  -0.352 7.537   H62  3HC 84 
3HC HN4  HN4  H 0 1 N N N 37.809 41.984 44.150 -0.352 0.427  10.088  HN4  3HC 85 
3HC H31  1H3  H 0 1 N N N 38.210 44.075 43.139 2.028  -0.289 11.427  H31  3HC 86 
3HC H32  2H3  H 0 1 N N N 38.376 44.801 44.649 0.686  -1.221 12.132  H32  3HC 87 
3HC H21  1H2  H 0 1 N N N 40.742 43.789 44.988 -0.544 0.885  12.576  H21  3HC 88 
3HC H22  2H2  H 0 1 N N N 40.572 42.773 43.661 0.798  1.817  11.871  H22  3HC 89 
3HC HC21 1HC2 H 0 0 N N N 39.666 45.666 39.343 2.269  2.892  16.095  HC21 3HC 90 
3HC HC22 2HC2 H 0 0 N N N 40.433 46.743 40.456 0.926  1.960  16.799  HC22 3HC 91 
3HC HC31 1HC3 H 0 0 N N N 41.464 44.733 38.647 0.748  4.820  15.747  HC31 3HC 92 
3HC HO31 1HO3 H 0 0 N N N 42.879 46.291 37.920 -1.119 3.145  17.094  HO31 3HC 93 
3HC HC41 1HC4 H 0 0 N N N 43.932 44.577 39.266 0.421  5.397  18.137  HC41 3HC 94 
3HC HC42 2HC4 H 0 0 N N N 43.216 45.000 40.870 0.660  3.691  18.582  HC42 3HC 95 
3HC HC43 3HC4 H 0 0 N N N 42.569 43.649 40.007 2.003  4.623  17.877  HC43 3HC 96 
# 
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 
3HC N1A C2A  SING Y N 1  
3HC N1A C6A  DOUB Y N 2  
3HC C2A N3A  DOUB Y N 3  
3HC C2A H2A  SING N N 4  
3HC N3A C4A  SING Y N 5  
3HC C4A C5A  DOUB Y N 6  
3HC C4A N9A  SING Y N 7  
3HC C5A C6A  SING Y N 8  
3HC C5A N7A  SING Y N 9  
3HC C6A N6A  SING N N 10 
3HC N6A H61A SING N N 11 
3HC N6A H62A SING N N 12 
3HC N7A C8A  DOUB Y N 13 
3HC C8A N9A  SING Y N 14 
3HC C8A H8A  SING N N 15 
3HC N9A C1B  SING N N 16 
3HC C1B C2B  SING N N 17 
3HC C1B O4B  SING N N 18 
3HC C1B H1B  SING N N 19 
3HC C2B O2B  SING N N 20 
3HC C2B C3B  SING N N 21 
3HC C2B H2B  SING N N 22 
3HC O2B HO2A SING N N 23 
3HC C3B O3B  SING N N 24 
3HC C3B C4B  SING N N 25 
3HC C3B H3B  SING N N 26 
3HC O3B P3B  SING N N 27 
3HC P3B O7A  DOUB N N 28 
3HC P3B O8A  SING N N 29 
3HC P3B O9A  SING N N 30 
3HC O8A HOA8 SING N N 31 
3HC O9A HOA9 SING N N 32 
3HC C4B O4B  SING N N 33 
3HC C4B C5B  SING N N 34 
3HC C4B H4B  SING N N 35 
3HC C5B O5B  SING N N 36 
3HC C5B H51A SING N N 37 
3HC C5B H52A SING N N 38 
3HC O5B P1A  SING N N 39 
3HC P1A O1A  DOUB N N 40 
3HC P1A O2A  SING N N 41 
3HC P1A O3A  SING N N 42 
3HC O2A HOA2 SING N N 43 
3HC O3A P2A  SING N N 44 
3HC P2A O4A  DOUB N N 45 
3HC P2A O5A  SING N N 46 
3HC P2A O6A  SING N N 47 
3HC O5A HOA5 SING N N 48 
3HC O6A CCP  SING N N 49 
3HC CBP CCP  SING N N 50 
3HC CBP CDP  SING N N 51 
3HC CBP CEP  SING N N 52 
3HC CBP CAP  SING N N 53 
3HC CCP H121 SING N N 54 
3HC CCP H122 SING N N 55 
3HC CDP H131 SING N N 56 
3HC CDP H132 SING N N 57 
3HC CDP H133 SING N N 58 
3HC CEP H141 SING N N 59 
3HC CEP H142 SING N N 60 
3HC CEP H143 SING N N 61 
3HC CAP OAP  SING N N 62 
3HC CAP C9P  SING N N 63 
3HC CAP H10  SING N N 64 
3HC OAP HO1  SING N N 65 
3HC C9P O9P  DOUB N N 66 
3HC C9P N8P  SING N N 67 
3HC N8P C7P  SING N N 68 
3HC N8P HN8  SING N N 69 
3HC C7P C6P  SING N N 70 
3HC C7P H71  SING N N 71 
3HC C7P H72  SING N N 72 
3HC C6P C5P  SING N N 73 
3HC C6P H61  SING N N 74 
3HC C6P H62  SING N N 75 
3HC C5P O5P  DOUB N N 76 
3HC C5P N4P  SING N N 77 
3HC N4P C3P  SING N N 78 
3HC N4P HN4  SING N N 79 
3HC C3P C2P  SING N N 80 
3HC C3P H31  SING N N 81 
3HC C3P H32  SING N N 82 
3HC C2P S1P  SING N N 83 
3HC C2P H21  SING N N 84 
3HC C2P H22  SING N N 85 
3HC S1P C1   SING N N 86 
3HC C1  O1   DOUB N N 87 
3HC C1  C2   SING N N 88 
3HC C2  C3   SING N N 89 
3HC C2  HC21 SING N N 90 
3HC C2  HC22 SING N N 91 
3HC C3  O3   SING N N 92 
3HC C3  C4   SING N N 93 
3HC C3  HC31 SING N N 94 
3HC O3  HO31 SING N N 95 
3HC C4  HC41 SING N N 96 
3HC C4  HC42 SING N N 97 
3HC C4  HC43 SING N N 98 
# 
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 
3HC SMILES           ACDLabs              10.04 O=C(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)CC(O)C 
3HC InChI            InChI                1.02b 
;InChI=1/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14+,18+,19+,20-,24+/m0/s1/f/h27-28,39-40,42,44H,26H2
;
3HC InChIKey         InChI                1.02b QHHKKMYHDBRONY-OSYRLUNDDT 
3HC SMILES_CANONICAL CACTVS               3.341 C[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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 
3HC SMILES           CACTVS               3.341 C[CH](O)CC(=O)SCCNC(=O)CCNC(=O)[CH](O)C(C)(C)CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23 
3HC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(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)O)O 
3HC SMILES           "OpenEye OEToolkits" 1.5.0 CC(CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)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 
3HC "SYSTEMATIC NAME" ACDLabs              10.04 
;S-{(9R,13S,15R)-17-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-9,13,15-trihydroxy-10,10-dimethyl-13,15-dioxido-4,8-dioxo-12,14,16-trioxa-3,7-diaza-13,15-diphosphaheptadec-1-yl} (3S)-3-hydroxybutanethioate (non-preferred name)
;
3HC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"S-[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]ethyl] 3-hydroxybutanethioate" 
# 
