data_AMP
# 
_chem_comp.id                                    AMP 
_chem_comp.name                                  "ADENOSINE MONOPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H14 N5 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        347.221 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AMP 
_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        ? 
_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 
AMP P      P    P 0 1 N N N 8.043  39.686 18.813 -4.788 0.931  -0.154 P      AMP 1  
AMP O1P    O1P  O 0 1 N N N 7.774  40.637 19.995 -5.661 -0.201 0.231  O1P    AMP 2  
AMP O2P    O2P  O 0 1 N N N 6.883  38.784 18.643 -4.479 1.835  1.141  O2P    AMP 3  
AMP O3P    O3P  O 0 1 N N N 9.316  38.856 19.092 -5.530 1.826  -1.268 O3P    AMP 4  
AMP "O5'"  O5*  O 0 1 N N N 8.290  40.534 17.463 -3.407 0.363  -0.755 "O5'"  AMP 5  
AMP "C5'"  C5*  C 0 1 N N N 9.275  41.545 17.412 -2.857 -0.513 0.231  "C5'"  AMP 6  
AMP "C4'"  C4*  C 0 1 N N R 9.922  41.617 16.032 -1.535 -1.090 -0.279 "C4'"  AMP 7  
AMP "O4'"  O4*  O 0 1 N N N 10.626 40.417 15.752 -0.544 -0.046 -0.401 "O4'"  AMP 8  
AMP "C3'"  C3*  C 0 1 N N S 8.899  41.815 14.923 -0.943 -2.078 0.750  "C3'"  AMP 9  
AMP "O3'"  O3*  O 0 1 N N N 9.238  42.933 14.133 -1.257 -3.425 0.389  "O3'"  AMP 10 
AMP "C2'"  C2*  C 0 1 N N R 8.933  40.529 14.114 0.582  -1.836 0.670  "C2'"  AMP 11 
AMP "O2'"  O2*  O 0 1 N N N 8.932  40.781 12.726 1.257  -3.027 0.260  "O2'"  AMP 12 
AMP "C1'"  C1*  C 0 1 N N R 10.220 39.828 14.530 0.729  -0.728 -0.396 "C1'"  AMP 13 
AMP N9     N9   N 0 1 Y N N 10.093 38.369 14.756 1.802  0.198  -0.025 N9     AMP 14 
AMP C8     C8   C 0 1 Y N N 9.377  37.767 15.753 1.658  1.363  0.669  C8     AMP 15 
AMP N7     N7   N 0 1 Y N N 9.495  36.418 15.645 2.817  1.935  0.823  N7     AMP 16 
AMP C5     C5   C 0 1 Y N N 10.287 36.160 14.586 3.776  1.173  0.244  C5     AMP 17 
AMP C6     C6   C 0 1 Y N N 10.707 34.951 14.063 5.168  1.286  0.090  C6     AMP 18 
AMP N6     N6   N 0 1 N N N 10.337 33.806 14.627 5.853  2.370  0.611  N6     AMP 19 
AMP N1     N1   N 0 1 Y N N 11.551 34.995 12.959 5.813  0.324  -0.563 N1     AMP 20 
AMP C2     C2   C 0 1 Y N N 11.915 36.195 12.375 5.168  -0.714 -1.063 C2     AMP 21 
AMP N3     N3   N 0 1 Y N N 11.488 37.403 12.902 3.864  -0.858 -0.948 N3     AMP 22 
AMP C4     C4   C 0 1 Y N N 10.672 37.369 14.001 3.135  0.053  -0.312 C4     AMP 23 
AMP HOP2   2HOP H 0 0 N N N 6.504  38.591 19.493 -3.909 2.559  0.848  HOP2   AMP 24 
AMP HOP3   3HOP H 0 0 N N N 9.769  38.686 18.275 -6.351 2.146  -0.869 HOP3   AMP 25 
AMP "H5'1" 1H5* H 0 0 N N N 8.803  42.513 17.635 -3.557 -1.325 0.426  "H5'1" AMP 26 
AMP "H5'2" 2H5* H 0 0 N N N 10.055 41.310 18.151 -2.679 0.043  1.152  "H5'2" AMP 27 
AMP "H4'"  H4*  H 0 1 N N N 10.602 42.481 16.057 -1.684 -1.585 -1.239 "H4'"  AMP 28 
AMP "H3'"  H3*  H 0 1 N N N 7.891  42.013 15.315 -1.315 -1.855 1.750  "H3'"  AMP 29 
AMP "HO3'" *HO3 H 0 0 N N N 9.314  43.701 14.687 -0.864 -3.994 1.065  "HO3'" AMP 30 
AMP "H2'"  H2*  H 0 1 N N N 8.041  39.916 14.308 0.965  -1.492 1.631  "H2'"  AMP 31 
AMP "HO2'" *HO2 H 0 0 N N N 8.932  41.719 12.574 1.078  -3.696 0.935  "HO2'" AMP 32 
AMP "H1'"  H1*  H 0 1 N N N 10.936 39.949 13.704 0.928  -1.166 -1.374 "H1'"  AMP 33 
AMP H8     H8   H 0 1 N N N 8.806  38.284 16.510 0.720  1.754  1.036  H8     AMP 34 
AMP HN61   1HN6 H 0 0 N N N 10.727 33.035 14.125 6.814  2.434  0.501  HN61   AMP 35 
AMP HN62   2HN6 H 0 0 N N N 9.754  33.727 15.435 5.370  3.067  1.082  HN62   AMP 36 
AMP H2     H2   H 0 1 N N N 12.541 36.190 11.495 5.731  -1.472 -1.587 H2     AMP 37 
# 
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 
AMP P     O1P    DOUB N N 1  
AMP P     O2P    SING N N 2  
AMP P     O3P    SING N N 3  
AMP P     "O5'"  SING N N 4  
AMP O2P   HOP2   SING N N 5  
AMP O3P   HOP3   SING N N 6  
AMP "O5'" "C5'"  SING N N 7  
AMP "C5'" "C4'"  SING N N 8  
AMP "C5'" "H5'1" SING N N 9  
AMP "C5'" "H5'2" SING N N 10 
AMP "C4'" "O4'"  SING N N 11 
AMP "C4'" "C3'"  SING N N 12 
AMP "C4'" "H4'"  SING N N 13 
AMP "O4'" "C1'"  SING N N 14 
AMP "C3'" "O3'"  SING N N 15 
AMP "C3'" "C2'"  SING N N 16 
AMP "C3'" "H3'"  SING N N 17 
AMP "O3'" "HO3'" SING N N 18 
AMP "C2'" "O2'"  SING N N 19 
AMP "C2'" "C1'"  SING N N 20 
AMP "C2'" "H2'"  SING N N 21 
AMP "O2'" "HO2'" SING N N 22 
AMP "C1'" N9     SING N N 23 
AMP "C1'" "H1'"  SING N N 24 
AMP N9    C8     SING Y N 25 
AMP N9    C4     SING Y N 26 
AMP C8    N7     DOUB Y N 27 
AMP C8    H8     SING N N 28 
AMP N7    C5     SING Y N 29 
AMP C5    C6     SING Y N 30 
AMP C5    C4     DOUB Y N 31 
AMP C6    N6     SING N N 32 
AMP C6    N1     DOUB Y N 33 
AMP N6    HN61   SING N N 34 
AMP N6    HN62   SING N N 35 
AMP N1    C2     SING Y N 36 
AMP C2    N3     DOUB Y N 37 
AMP C2    H2     SING N N 38 
AMP N3    C4     SING Y N 39 
# 
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 
AMP SMILES           ACDLabs              10.04 O=P(O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O                                                                                                                                     
AMP InChI            InChI                1.02b InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1/f/h18-19H,11H2 
AMP InChIKey         InChI                1.02b UDMBCSSLTHHNCD-WLZLVAIBDR                                                                                                                                                    
AMP SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]3O                                                                                                                 
AMP SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O                                                                                                                       
AMP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N                                                                                                             
AMP SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=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 
AMP "SYSTEMATIC NAME" ACDLabs              10.04 
;5'-adenylic acid
;
AMP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
