data_A23
# 
_chem_comp.id                                    A23 
_chem_comp.name                                  
;ADENOSINE-5'-PHOSPHATE-2',3'-CYCLIC PHOSPHATE
;
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H13 N5 O9 P2" 
_chem_comp.mon_nstd_parent_comp_id               A 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-10-08 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        409.186 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     A23 
_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        1D4R 
_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 
A23 PC     PC   P 0 1 N N S 13.205 -16.575 -50.946 -3.562 0.129  0.153  PC     A23 1  
A23 O1C    O1C  O 0 1 N N N 11.725 -16.500 -50.780 -4.605 -0.909 0.296  O1C    A23 2  
A23 O2C    O2C  O 0 1 N N N 13.867 -15.960 -52.124 -4.158 1.618  0.298  O2C    A23 3  
A23 P      P    P 0 1 N N N 16.904 -21.053 -46.210 1.660  -0.079 -4.784 P      A23 4  
A23 OP1    O1P  O 0 1 N N N 18.115 -20.395 -46.775 2.154  1.297  -4.556 OP1    A23 5  
A23 OP2    O2P  O 0 1 N N N 16.926 -22.520 -45.963 2.846  -0.980 -5.397 OP2    A23 6  
A23 OP3    O3P  O 0 1 N Y N 16.530 -20.308 -44.829 0.425  -0.042 -5.816 OP3    A23 7  
A23 "O5'"  O5*  O 0 1 N N N 15.662 -20.739 -47.154 1.173  -0.713 -3.387 "O5'"  A23 8  
A23 "C5'"  C5*  C 0 1 N N N 15.840 -20.024 -48.367 0.126  0.126  -2.895 "C5'"  A23 9  
A23 "C4'"  C4*  C 0 1 N N R 14.520 -19.493 -48.898 -0.384 -0.423 -1.562 "C4'"  A23 10 
A23 "O4'"  O4*  O 0 1 N N N 13.655 -19.066 -47.806 0.676  -0.428 -0.581 "O4'"  A23 11 
A23 "C3'"  C3*  C 0 1 N N R 14.720 -18.272 -49.778 -1.463 0.510  -0.970 "C3'"  A23 12 
A23 "O3'"  O3*  O 0 1 N N N 13.741 -18.066 -50.785 -2.761 -0.040 -1.258 "O3'"  A23 13 
A23 "C2'"  C2*  C 0 1 N N R 14.534 -17.084 -48.810 -1.200 0.474  0.551  "C2'"  A23 14 
A23 "O2'"  O2*  O 0 1 N N N 13.883 -16.095 -49.589 -2.346 -0.115 1.213  "O2'"  A23 15 
A23 "C1'"  C1*  C 0 1 N N R 13.530 -17.653 -47.807 0.009  -0.474 0.699  "C1'"  A23 16 
A23 N9     N9   N 0 1 Y N N 13.725 -17.165 -46.437 0.904  0.000  1.757  N9     A23 17 
A23 C8     C8   C 0 1 Y N N 14.661 -17.582 -45.520 1.935  0.880  1.607  C8     A23 18 
A23 N7     N7   N 0 1 Y N N 14.590 -16.960 -44.368 2.519  1.080  2.753  N7     A23 19 
A23 C5     C5   C 0 1 Y N N 13.541 -16.066 -44.533 1.898  0.348  3.709  C5     A23 20 
A23 C6     C6   C 0 1 Y N N 12.968 -15.105 -43.670 2.088  0.161  5.089  C6     A23 21 
A23 N6     N6   N 0 1 N N N 13.410 -14.866 -42.422 3.100  0.825  5.761  N6     A23 22 
A23 N1     N1   N 0 1 Y N N 11.923 -14.383 -44.140 1.270  -0.664 5.734  N1     A23 23 
A23 C2     C2   C 0 1 Y N N 11.501 -14.611 -45.393 0.303  -1.301 5.101  C2     A23 24 
A23 N3     N3   N 0 1 Y N N 11.965 -15.476 -46.302 0.091  -1.161 3.809  N3     A23 25 
A23 C4     C4   C 0 1 Y N N 12.996 -16.182 -45.802 0.858  -0.357 3.081  C4     A23 26 
A23 HOC2   2HOC H 0 0 N N N 14.809 -16.007 -52.229 -4.617 1.654  1.148  HOC2   A23 27 
A23 HOP2   2HOP H 0 0 N N N 16.153 -22.939 -45.602 3.108  -0.566 -6.231 HOP2   A23 28 
A23 HOP3   3HOP H 0 0 N N N 15.757 -20.727 -44.468 0.134  -0.956 -5.937 HOP3   A23 29 
A23 "H5'"  1H5* H 0 1 N N N 16.591 -19.208 -48.253 -0.690 0.147  -3.616 "H5'"  A23 30 
A23 "H5''" 2H5* H 0 0 N N N 16.368 -20.641 -49.130 0.509  1.136  -2.749 "H5''" A23 31 
A23 "H4'"  H4*  H 0 1 N N N 14.064 -20.328 -49.478 -0.783 -1.428 -1.694 "H4'"  A23 32 
A23 "H3'"  H3*  H 0 1 N N N 15.700 -18.387 -50.295 -1.369 1.522  -1.365 "H3'"  A23 33 
A23 "H2'"  H2*  H 0 1 N N N 15.452 -16.674 -48.329 -0.976 1.461  0.957  "H2'"  A23 34 
A23 "H1'"  H1*  H 0 1 N N N 12.516 -17.316 -48.128 -0.327 -1.488 0.915  "H1'"  A23 35 
A23 H8     H8   H 0 1 N N N 15.418 -18.363 -45.696 2.224  1.342  0.675  H8     A23 36 
A23 HN61   1HN6 H 0 0 N N N 12.996 -14.172 -41.799 3.218  0.690  6.714  HN61   A23 37 
A23 HN62   2HN6 H 0 0 N N N 14.405 -14.654 -42.490 3.692  1.421  5.278  HN62   A23 38 
A23 H2     H2   H 0 1 N N N 10.646 -13.996 -45.724 -0.338 -1.962 5.664  H2     A23 39 
# 
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 
A23 PC    O1C    DOUB N N 1  
A23 PC    O2C    SING N N 2  
A23 PC    "O3'"  SING N N 3  
A23 PC    "O2'"  SING N N 4  
A23 O2C   HOC2   SING N N 5  
A23 P     OP1    DOUB N N 6  
A23 P     OP2    SING N N 7  
A23 P     OP3    SING N N 8  
A23 P     "O5'"  SING N N 9  
A23 OP2   HOP2   SING N N 10 
A23 OP3   HOP3   SING N N 11 
A23 "O5'" "C5'"  SING N N 12 
A23 "C5'" "C4'"  SING N N 13 
A23 "C5'" "H5'"  SING N N 14 
A23 "C5'" "H5''" SING N N 15 
A23 "C4'" "O4'"  SING N N 16 
A23 "C4'" "C3'"  SING N N 17 
A23 "C4'" "H4'"  SING N N 18 
A23 "O4'" "C1'"  SING N N 19 
A23 "C3'" "O3'"  SING N N 20 
A23 "C3'" "C2'"  SING N N 21 
A23 "C3'" "H3'"  SING N N 22 
A23 "C2'" "O2'"  SING N N 23 
A23 "C2'" "C1'"  SING N N 24 
A23 "C2'" "H2'"  SING N N 25 
A23 "C1'" N9     SING N N 26 
A23 "C1'" "H1'"  SING N N 27 
A23 N9    C8     SING Y N 28 
A23 N9    C4     SING Y N 29 
A23 C8    N7     DOUB Y N 30 
A23 C8    H8     SING N N 31 
A23 N7    C5     SING Y N 32 
A23 C5    C6     SING Y N 33 
A23 C5    C4     DOUB Y N 34 
A23 C6    N6     SING N N 35 
A23 C6    N1     DOUB Y N 36 
A23 N6    HN61   SING N N 37 
A23 N6    HN62   SING N N 38 
A23 N1    C2     SING Y N 39 
A23 C2    N3     DOUB Y N 40 
A23 C2    H2     SING N N 41 
A23 N3    C4     SING Y N 42 
# 
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 
A23 SMILES           ACDLabs              10.04 "O=P1(OC2C(OC(C2O1)COP(=O)(O)O)n3c4ncnc(N)c4nc3)O"                                                                                                                                               
A23 InChI            InChI                1.02b "InChI=1/C10H13N5O9P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(23-26(19,20)24-7)4(22-10)1-21-25(16,17)18/h2-4,6-7,10H,1H2,(H,19,20)(H2,11,12,13)(H2,16,17,18)/t4-,6-,7-,10-/m1/s1/f/h16-17,19H,11H2" 
A23 InChIKey         InChI                1.02b HJMBCNJTGVMDOA-ZKZQFZQIDO                                                                                                                                                                        
A23 SMILES_CANONICAL CACTVS               3.341 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@H]4O[P@@](O)(=O)O[C@@H]34"                                                                                                                       
A23 SMILES           CACTVS               3.341 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(O)=O)[CH]4O[P](O)(=O)O[CH]34"                                                                                                                               
A23 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@H]4[C@@H]([C@H](O3)COP(=O)(O)O)O[P@@](=O)(O4)O)N"                                                                                                                    
A23 SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C4C(C(O3)COP(=O)(O)O)OP(=O)(O4)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 
A23 "SYSTEMATIC NAME" ACDLabs              10.04 "[(2S,3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2-hydroxy-2-oxidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]methyl dihydrogen phosphate" 
A23 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R,3S,5R,6R,8R)-6-(6-aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3$l^{5}-phosphabicyclo[3.3.0]octan-8-yl]methyl dihydrogen phosphate"  
# 
