data_4AD
# 
_chem_comp.id                                    4AD 
_chem_comp.name                                  
;4-AMINO-1,4-DIOXOBUTAN-2-AMINIUM ADENOSINE-5'-MONOPHOSPHATE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H21 N7 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ASNAMP 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2005-05-20 
_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                        462.332 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4AD 
_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        1X54 
_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 
4AD O2P    O2P  O 0 1 N N N -1.420 8.770  41.940 2.964  -2.612 -0.628 O2P    4AD 1  
4AD P      P    P 0 1 N N R -2.791 9.305  41.680 2.565  -1.196 -0.470 P      4AD 2  
4AD O1P    O1P  O 0 1 N N N -3.003 10.783 41.502 2.259  -0.560 -1.917 O1P    4AD 3  
4AD O3P    O3P  O 0 1 N N N -3.661 8.789  42.943 3.758  -0.377 0.235  O3P    4AD 4  
4AD C      C    C 0 1 N N N -5.061 9.002  43.156 4.990  -0.394 -0.298 C      4AD 5  
4AD O      O    O 0 1 N N N -5.754 9.720  42.428 5.203  -1.023 -1.307 O      4AD 6  
4AD CA     CA   C 0 1 N N S -5.585 8.278  44.348 6.107  0.373  0.362  CA     4AD 7  
4AD N      N    N 1 1 N N N -6.722 8.992  44.897 7.399  -0.159 -0.089 N      4AD 8  
4AD CB     CB   C 0 1 N N N -5.958 6.890  43.825 6.004  1.852  -0.016 CB     4AD 9  
4AD CG     CG   C 0 1 N N N -6.517 6.044  44.941 7.044  2.637  0.740  CG     4AD 10 
4AD OD1    OD1  O 0 1 N N N -5.828 5.777  45.918 7.794  2.070  1.506  OD1    4AD 11 
4AD ND2    ND2  N 0 1 N N N -7.772 5.612  44.784 7.141  3.970  0.565  ND2    4AD 12 
4AD "O5'"  O5*  O 0 1 N N N -3.488 8.579  40.425 1.242  -1.111 0.443  "O5'"  4AD 13 
4AD "C5'"  C5*  C 0 1 N N N -3.606 7.151  40.388 0.260  -1.948 -0.171 "C5'"  4AD 14 
4AD "C4'"  C4*  C 0 1 N N R -3.098 6.698  39.026 -1.029 -1.911 0.652  "C4'"  4AD 15 
4AD "C3'"  C3*  C 0 1 N N S -1.633 7.033  38.740 -2.054 -2.901 0.065  "C3'"  4AD 16 
4AD "O3'"  O3*  O 0 1 N N N -0.769 6.026  39.284 -2.413 -3.892 1.030  "O3'"  4AD 17 
4AD "C2'"  C2*  C 0 1 N N R -1.594 7.035  37.229 -3.278 -2.013 -0.283 "C2'"  4AD 18 
4AD "O2'"  O2*  O 0 1 N N N -1.515 5.674  36.770 -4.498 -2.672 0.061  "O2'"  4AD 19 
4AD "C1'"  C1*  C 0 1 N N R -2.961 7.572  36.856 -3.045 -0.773 0.618  "C1'"  4AD 20 
4AD "O4'"  O4*  O 0 1 N N N -3.814 7.367  37.981 -1.612 -0.599 0.588  "O4'"  4AD 21 
4AD N9     N9   N 0 1 Y N N -2.937 9.004  36.454 -3.719 0.404  0.064  N9     4AD 22 
4AD C4     C4   C 0 1 Y N N -2.983 9.504  35.230 -5.008 0.798  0.322  C4     4AD 23 
4AD N3     N3   N 0 1 Y N N -3.056 8.900  34.027 -5.997 0.334  1.079  N3     4AD 24 
4AD C2     C2   C 0 1 Y N N -3.103 9.668  32.928 -7.156 0.957  1.125  C2     4AD 25 
4AD N1     N1   N 0 1 Y N N -3.066 11.010 33.029 -7.395 2.060  0.440  N1     4AD 26 
4AD C6     C6   C 0 1 Y N N -2.974 11.667 34.216 -6.464 2.601  -0.340 C6     4AD 27 
4AD N6     N6   N 0 1 N N N -2.950 13.024 34.240 -6.724 3.758  -1.055 N6     4AD 28 
4AD C5     C5   C 0 1 Y N N -2.929 10.906 35.387 -5.211 1.972  -0.422 C5     4AD 29 
4AD N7     N7   N 0 1 Y N N -2.846 11.241 36.715 -4.059 2.225  -1.090 N7     4AD 30 
4AD C8     C8   C 0 1 Y N N -2.844 10.003 37.502 -3.183 1.306  -0.806 C8     4AD 31 
4AD HOP1   1HOP H 0 0 N N N -3.874 11.123 41.337 2.003  0.361  -1.770 HOP1   4AD 32 
4AD HA     HA   H 0 1 N N N -4.858 8.202  45.170 6.029  0.268  1.445  HA     4AD 33 
4AD HN1    1HN  H 0 1 N N N -7.550 8.445  44.773 8.147  0.354  0.353  HN1    4AD 34 
4AD HN2    2HN  H 0 1 N N N -6.826 9.867  44.424 7.467  -1.135 0.160  HN2    4AD 35 
4AD HN3    3HN  H 0 1 N N N -6.574 9.156  45.872 7.471  -0.063 -1.091 HN3    4AD 36 
4AD HB1    1HB  H 0 1 N N N -5.057 6.404  43.424 5.011  2.224  0.239  HB1    4AD 37 
4AD HB2    2HB  H 0 1 N N N -6.716 6.993  43.034 6.170  1.965  -1.087 HB2    4AD 38 
4AD HD21   1HD2 H 0 0 N N N -8.366 5.798  44.001 7.811  4.476  1.051  HD21   4AD 39 
4AD HD22   2HD2 H 0 0 N N N -8.010 5.070  45.590 6.544  4.423  -0.051 HD22   4AD 40 
4AD "H5'1" 1H5* H 0 0 N N N -4.650 6.840  40.540 0.057  -1.590 -1.180 "H5'1" 4AD 41 
4AD "H5'2" 2H5* H 0 0 N N N -3.005 6.697  41.190 0.633  -2.971 -0.217 "H5'2" 4AD 42 
4AD "H4'"  H4*  H 0 1 N N N -3.236 5.607  39.050 -0.814 -2.172 1.688  "H4'"  4AD 43 
4AD "H3'"  H3*  H 0 1 N N N -1.294 7.980  39.186 -1.657 -3.372 -0.835 "H3'"  4AD 44 
4AD H2     H2   H 0 1 N N N -0.578 5.378  38.616 -3.098 -4.441 0.625  H2     4AD 45 
4AD "H2'"  H2*  H 0 1 N N N -0.753 7.607  36.810 -3.271 -1.735 -1.337 "H2'"  4AD 46 
4AD H1     H1   H 0 1 N N N -1.498 5.660  35.820 -4.583 -3.430 -0.533 H1     4AD 47 
4AD "H1'"  H1*  H 0 1 N N N -3.332 7.034  35.971 -3.388 -0.968 1.634  "H1'"  4AD 48 
4AD H3     H3   H 0 1 N N N -3.171 9.206  31.954 -7.940 0.552  1.747  H3     4AD 49 
4AD HN61   1HN6 H 0 0 N N N -2.892 13.589 35.063 -6.037 4.143  -1.621 HN61   4AD 50 
4AD HN62   2HN6 H 0 0 N N N -3.000 13.367 33.302 -7.593 4.183  -0.990 HN62   4AD 51 
4AD H8     H8   H 0 1 N N N -2.788 9.871  38.572 -2.179 1.264  -1.201 H8     4AD 52 
# 
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 
4AD O2P   P      DOUB N N 1  
4AD P     O1P    SING N N 2  
4AD P     O3P    SING N N 3  
4AD P     "O5'"  SING N N 4  
4AD O1P   HOP1   SING N N 5  
4AD O3P   C      SING N N 6  
4AD C     O      DOUB N N 7  
4AD C     CA     SING N N 8  
4AD CA    N      SING N N 9  
4AD CA    CB     SING N N 10 
4AD CA    HA     SING N N 11 
4AD N     HN1    SING N N 12 
4AD N     HN2    SING N N 13 
4AD N     HN3    SING N N 14 
4AD CB    CG     SING N N 15 
4AD CB    HB1    SING N N 16 
4AD CB    HB2    SING N N 17 
4AD CG    OD1    DOUB N N 18 
4AD CG    ND2    SING N N 19 
4AD ND2   HD21   SING N N 20 
4AD ND2   HD22   SING N N 21 
4AD "O5'" "C5'"  SING N N 22 
4AD "C5'" "C4'"  SING N N 23 
4AD "C5'" "H5'1" SING N N 24 
4AD "C5'" "H5'2" SING N N 25 
4AD "C4'" "C3'"  SING N N 26 
4AD "C4'" "O4'"  SING N N 27 
4AD "C4'" "H4'"  SING N N 28 
4AD "C3'" "O3'"  SING N N 29 
4AD "C3'" "C2'"  SING N N 30 
4AD "C3'" "H3'"  SING N N 31 
4AD "O3'" H2     SING N N 32 
4AD "C2'" "O2'"  SING N N 33 
4AD "C2'" "C1'"  SING N N 34 
4AD "C2'" "H2'"  SING N N 35 
4AD "O2'" H1     SING N N 36 
4AD "C1'" "O4'"  SING N N 37 
4AD "C1'" N9     SING N N 38 
4AD "C1'" "H1'"  SING N N 39 
4AD N9    C4     SING Y N 40 
4AD N9    C8     SING Y N 41 
4AD C4    N3     SING Y N 42 
4AD C4    C5     DOUB Y N 43 
4AD N3    C2     DOUB Y N 44 
4AD C2    N1     SING Y N 45 
4AD C2    H3     SING N N 46 
4AD N1    C6     DOUB Y N 47 
4AD C6    N6     SING N N 48 
4AD C6    C5     SING Y N 49 
4AD N6    HN61   SING N N 50 
4AD N6    HN62   SING N N 51 
4AD C5    N7     SING Y N 52 
4AD N7    C8     DOUB Y N 53 
4AD C8    H8     SING N N 54 
# 
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 
4AD SMILES           ACDLabs              10.04 O=C(N)CC(C(=O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)[NH3+] 
4AD InChI            InChI                1.02b 
InChI=1/C14H20N7O9P/c15-5(1-7(16)22)14(25)30-31(26,27)28-2-6-9(23)10(24)13(29-6)21-4-20-8-11(17)18-3-19-12(8)21/h3-6,9-10,13,23-24H,1-2,15H2,(H2,16,22)(H,26,27)(H2,17,18,19)/p+1/t5-,6+,9+,10+,13+/m0/s1/fC14H21N7O9P/h15,26H,16-17H2/q+1 
4AD InChIKey         InChI                1.02b BZHVCXQAFQWXPZ-HYKIZMBYDK 
4AD SMILES_CANONICAL CACTVS               3.341 NC(=O)C[C@H]([NH3+])C(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23 
4AD SMILES           CACTVS               3.341 NC(=O)C[CH]([NH3+])C(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23 
4AD 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)OC(=O)[C@H](CC(=O)N)[NH3+])O)O)N 
4AD SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC(=O)C(CC(=O)N)[NH3+])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 
4AD "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(R)-{[(2S)-4-amino-2-ammonio-4-oxobutanoyl]oxy}(hydroxy)phosphoryl]adenosine"                                                        
4AD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [(2S)-4-amino-1-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-1,4-dioxo-butan-2-yl]azanium 
# 
