data_ACQ
# 
_chem_comp.id                                    ACQ 
_chem_comp.name                                  "DIPHOSPHOMETHYLPHOSPHONIC ACID ADENYLATE ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H19 N5 O15 P4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;ADENOSINE-5'-[BETA, GAMMA-METHYLENE]TETRAPHOSPHATE
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-06-12 
_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                        585.188 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ACQ 
_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        1JBW 
_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 
ACQ PG     PG   P 0 1 N N S 13.894 2.022  16.315 0.486  -0.171 -5.885  PG     ACQ 1  
ACQ O1G    O1G  O 0 1 N N N 13.865 3.523  16.163 1.022  1.204  -5.778  O1G    ACQ 2  
ACQ O2G    O2G  O 0 1 N N N 13.763 1.541  17.740 -1.052 -0.112 -6.354  O2G    ACQ 3  
ACQ O3G    O3G  O 0 1 N N N 12.924 1.200  15.296 1.345  -0.999 -6.966  O3G    ACQ 4  
ACQ PB     PB   P 0 1 N N S 17.093 1.743  16.663 -0.376 -0.056 -3.038  PB     ACQ 5  
ACQ O1B    O1B  O 0 1 N N N 17.008 1.094  18.004 -1.791 -0.002 -3.470  O1B    ACQ 6  
ACQ O2B    O2B  O 0 1 N N N 17.544 3.175  16.548 0.206  1.440  -2.922  O2B    ACQ 7  
ACQ C3B    C3B  C 0 1 N N N 15.502 1.454  15.896 0.595  -0.994 -4.262  C3B    ACQ 8  
ACQ PA     PA   P 0 1 N N R 18.678 -0.479 15.876 -1.157 0.094  -0.578  PA     ACQ 9  
ACQ O1A    O1A  O 0 1 N N N 17.743 -1.504 16.397 -2.560 0.146  -1.048  O1A    ACQ 10 
ACQ O2A    O2A  O 0 1 N N N 19.978 -0.359 16.562 -0.561 1.588  -0.504  O2A    ACQ 11 
ACQ O3A    O3A  O 0 1 N N N 17.877 0.829  15.711 -0.280 -0.782 -1.605  O3A    ACQ 12 
ACQ "O5'"  O5*  O 0 1 N N N 18.950 -0.659 14.315 -1.104 -0.578 0.882   "O5'"  ACQ 13 
ACQ "C5'"  C5*  C 0 1 N N N 17.826 -0.846 13.403 -1.897 0.241  1.743   "C5'"  ACQ 14 
ACQ "C4'"  C4*  C 0 1 N N R 18.253 -0.578 11.985 -1.889 -0.345 3.156   "C4'"  ACQ 15 
ACQ "O4'"  O4*  O 0 1 N N N 18.793 0.774  11.924 -0.545 -0.369 3.683   "O4'"  ACQ 16 
ACQ "C3'"  C3*  C 0 1 N N S 19.339 -1.468 11.512 -2.676 0.566  4.124   "C3'"  ACQ 17 
ACQ "O3'"  O3*  O 0 1 N N N 18.763 -2.676 10.992 -4.003 0.069  4.312   "O3'"  ACQ 18 
ACQ "C2'"  C2*  C 0 1 N N R 20.035 -0.637 10.479 -1.876 0.491  5.446   "C2'"  ACQ 19 
ACQ "O2'"  O2*  O 0 1 N N N 19.313 -0.617 9.235  -2.685 -0.051 6.491   "O2'"  ACQ 20 
ACQ "C1'"  C1*  C 0 1 N N R 19.940 0.822  11.020 -0.699 -0.453 5.116   "C1'"  ACQ 21 
ACQ N9     N9   N 0 1 Y N N 21.129 1.334  11.812 0.520  -0.001 5.789   N9     ACQ 22 
ACQ C8     C8   C 0 1 Y N N 21.523 1.042  13.098 1.429  0.887  5.298   C8     ACQ 23 
ACQ N7     N7   N 0 1 Y N N 22.593 1.673  13.529 2.391  1.060  6.157   N7     ACQ 24 
ACQ C5     C5   C 0 1 Y N N 22.937 2.433  12.454 2.159  0.299  7.253   C5     ACQ 25 
ACQ C6     C6   C 0 1 Y N N 23.994 3.365  12.244 2.837  0.075  8.463   C6     ACQ 26 
ACQ N6     N6   N 0 1 N N N 24.889 3.638  13.218 4.026  0.727  8.739   N6     ACQ 27 
ACQ N1     N1   N 0 1 Y N N 24.078 3.986  11.024 2.307  -0.771 9.340   N1     ACQ 28 
ACQ C2     C2   C 0 1 Y N N 23.178 3.711  10.058 1.172  -1.397 9.085   C2     ACQ 29 
ACQ N3     N3   N 0 1 Y N N 22.129 2.854  10.133 0.506  -1.223 7.963   N3     ACQ 30 
ACQ C4     C4   C 0 1 Y N N 22.062 2.241  11.379 0.958  -0.395 7.028   C4     ACQ 31 
ACQ PD     PD   P 0 1 N N N 12.081 1.337  13.908 1.204  -0.221 -8.368  PD     ACQ 32 
ACQ O1D    O1D  O 0 1 N N N 12.624 2.612  13.306 1.729  1.155  -8.223  O1D    ACQ 33 
ACQ O2D    O2D  O 0 1 N N N 12.353 0.110  13.050 2.044  -0.999 -9.500  O2D    ACQ 34 
ACQ O3D    O3D  O 0 1 N N N 10.599 1.428  14.240 -0.346 -0.161 -8.795  O3D    ACQ 35 
ACQ HOG2   2HOG H 0 0 N N N 13.781 0.596  17.835 -1.362 -1.026 -6.411  HOG2   ACQ 36 
ACQ HOB2   2HOB H 0 0 N N N 17.598 3.588  15.694 1.127  1.360  -2.640  HOB2   ACQ 37 
ACQ H3B1   1H3B H 0 0 N N N 15.406 0.343  15.853 1.637  -1.033 -3.944  H3B1   ACQ 38 
ACQ H3B2   2H3B H 0 0 N N N 15.641 1.760  14.833 0.201  -2.006 -4.340  H3B2   ACQ 39 
ACQ HOA2   2HOA H 0 0 N N N 20.577 0.298  16.228 0.351  1.509  -0.195  HOA2   ACQ 40 
ACQ "H5'1" 1H5* H 0 0 N N N 17.363 -1.854 13.514 -2.921 0.277  1.370   "H5'1" ACQ 41 
ACQ "H5'2" 2H5* H 0 0 N N N 16.945 -0.227 13.696 -1.484 1.250  1.766   "H5'2" ACQ 42 
ACQ "H4'"  H4*  H 0 1 N N N 17.353 -0.741 11.347 -2.313 -1.349 3.151   "H4'"  ACQ 43 
ACQ "H3'"  H3*  H 0 1 N N N 20.055 -1.804 12.296 -2.702 1.589  3.749   "H3'"  ACQ 44 
ACQ "HO3'" *HO3 H 0 0 N N N 19.459 -3.246 10.688 -4.444 0.675  4.923   "HO3'" ACQ 45 
ACQ "H2'"  H2*  H 0 1 N N N 21.063 -1.032 10.306 -1.506 1.477  5.724   "H2'"  ACQ 46 
ACQ "HO2'" *HO2 H 0 0 N N N 19.754 -0.089 8.579  -3.433 0.550  6.607   "HO2'" ACQ 47 
ACQ "H1'"  H1*  H 0 1 N N N 19.874 1.515  10.149 -0.939 -1.475 5.413   "H1'"  ACQ 48 
ACQ H8     H8   H 0 1 N N N 21.000 0.329  13.758 1.362  1.376  4.337   H8     ACQ 49 
ACQ HN61   1HN6 H 0 0 N N N 25.645 4.305  13.067 4.483  0.567  9.580   HN61   ACQ 50 
ACQ HN62   2HN6 H 0 0 N N N 25.301 2.756  13.524 4.405  1.340  8.090   HN62   ACQ 51 
ACQ H2     H2   H 0 1 N N N 23.314 4.245  9.102  0.777  -2.077 9.825   H2     ACQ 52 
ACQ HOD2   2HOD H 0 0 N N N 11.861 0.189  12.240 1.933  -0.501 -10.322 HOD2   ACQ 53 
ACQ HOD3   3HOD H 0 0 N N N 10.107 1.507  13.430 -0.648 -1.076 -8.879  HOD3   ACQ 54 
# 
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 
ACQ PG    O1G    DOUB N N 1  
ACQ PG    O2G    SING N N 2  
ACQ PG    O3G    SING N N 3  
ACQ PG    C3B    SING N N 4  
ACQ O2G   HOG2   SING N N 5  
ACQ O3G   PD     SING N N 6  
ACQ PB    O1B    DOUB N N 7  
ACQ PB    O2B    SING N N 8  
ACQ PB    C3B    SING N N 9  
ACQ PB    O3A    SING N N 10 
ACQ O2B   HOB2   SING N N 11 
ACQ C3B   H3B1   SING N N 12 
ACQ C3B   H3B2   SING N N 13 
ACQ PA    O1A    DOUB N N 14 
ACQ PA    O2A    SING N N 15 
ACQ PA    O3A    SING N N 16 
ACQ PA    "O5'"  SING N N 17 
ACQ O2A   HOA2   SING N N 18 
ACQ "O5'" "C5'"  SING N N 19 
ACQ "C5'" "C4'"  SING N N 20 
ACQ "C5'" "H5'1" SING N N 21 
ACQ "C5'" "H5'2" SING N N 22 
ACQ "C4'" "O4'"  SING N N 23 
ACQ "C4'" "C3'"  SING N N 24 
ACQ "C4'" "H4'"  SING N N 25 
ACQ "O4'" "C1'"  SING N N 26 
ACQ "C3'" "O3'"  SING N N 27 
ACQ "C3'" "C2'"  SING N N 28 
ACQ "C3'" "H3'"  SING N N 29 
ACQ "O3'" "HO3'" SING N N 30 
ACQ "C2'" "O2'"  SING N N 31 
ACQ "C2'" "C1'"  SING N N 32 
ACQ "C2'" "H2'"  SING N N 33 
ACQ "O2'" "HO2'" SING N N 34 
ACQ "C1'" N9     SING N N 35 
ACQ "C1'" "H1'"  SING N N 36 
ACQ N9    C8     SING Y N 37 
ACQ N9    C4     SING Y N 38 
ACQ C8    N7     DOUB Y N 39 
ACQ C8    H8     SING N N 40 
ACQ N7    C5     SING Y N 41 
ACQ C5    C6     SING Y N 42 
ACQ C5    C4     DOUB Y N 43 
ACQ C6    N6     SING N N 44 
ACQ C6    N1     DOUB Y N 45 
ACQ N6    HN61   SING N N 46 
ACQ N6    HN62   SING N N 47 
ACQ N1    C2     SING Y N 48 
ACQ C2    N3     DOUB Y N 49 
ACQ C2    H2     SING N N 50 
ACQ N3    C4     SING Y N 51 
ACQ PD    O1D    DOUB N N 52 
ACQ PD    O2D    SING N N 53 
ACQ PD    O3D    SING N N 54 
ACQ O2D   HOD2   SING N N 55 
ACQ O3D   HOD3   SING N N 56 
# 
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 
ACQ SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)CP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O 
ACQ InChI            InChI                1.02b 
InChI=1/C11H19N5O15P4/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(29-11)1-28-35(26,27)31-33(21,22)4-32(19,20)30-34(23,24)25/h2-3,5,7-8,11,17-18H,1,4H2,(H,19,20)(H,21,22)(H,26,27)(H2,12,13,14)(H2,23,24,25)/t5-,7-,8-,11-/m1/s1/f/h19,21,23-24,26H,12H2 
ACQ InChIKey         InChI                1.02b ARRGHMSEJJFDME-OUIBPIIPDS 
ACQ SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@](O)(=O)O[P@](O)(=O)C[P@@](O)(=O)O[P](O)(O)=O)[C@@H](O)[C@H]3O 
ACQ SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)C[P](O)(=O)O[P](O)(O)=O)[CH](O)[CH]3O 
ACQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(O)O[P@](=O)(C[P@](=O)(O)OP(=O)(O)O)O)O)O)N 
ACQ SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(CP(=O)(O)OP(=O)(O)O)O)O)O)N 
# 
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 
ACQ "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(R)-hydroxy{[(S)-hydroxy{[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}phosphoryl]oxy}phosphoryl]adenosine"                                         
ACQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]methyl-phosphonooxy-phosphinic acid" 
# 
