data_CMP
# 
_chem_comp.id                                    CMP 
_chem_comp.name                                  "ADENOSINE-3',5'-CYCLIC-MONOPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H12 N5 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CYCLIC AMP; CAMP" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2020-05-28 
_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                        329.206 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CMP 
_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        1RUN 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
CMP P      P    P 0 1 N N R 23.331 65.840 7.282 0.035  0.457  -4.129 P      CMP 1  
CMP O1P    O1P  O 0 1 N N N 24.410 65.875 8.285 1.127  1.448  -4.010 O1P    CMP 2  
CMP O2P    O2P  O 0 1 N N N 22.096 66.642 7.482 -0.773 0.723  -5.496 O2P    CMP 3  
CMP "O5'"  O5*  O 0 1 N N N 24.063 66.219 5.913 0.664  -1.020 -4.167 "O5'"  CMP 4  
CMP "C5'"  C5*  C 0 1 N N N 23.590 65.766 4.634 1.291  -1.282 -2.903 "C5'"  CMP 5  
CMP "C4'"  C4*  C 0 1 N N R 22.867 64.454 4.776 0.229  -1.157 -1.826 "C4'"  CMP 6  
CMP "O4'"  O4*  O 0 1 N N N 23.145 63.564 3.660 0.656  -1.453 -0.497 "O4'"  CMP 7  
CMP "C3'"  C3*  C 0 1 N N S 23.378 63.641 5.941 -0.193 0.332  -1.731 "C3'"  CMP 8  
CMP "O3'"  O3*  O 0 1 N N N 22.893 64.317 7.078 -0.970 0.624  -2.876 "O3'"  CMP 9  
CMP "C2'"  C2*  C 0 1 N N R 22.798 62.275 5.618 -0.954 0.340  -0.394 "C2'"  CMP 10 
CMP "O2'"  O2*  O 0 1 N N N 21.396 62.250 5.837 -2.353 0.144  -0.610 "O2'"  CMP 11 
CMP "C1'"  C1*  C 0 1 N N R 23.073 62.218 4.113 -0.331 -0.851 0.372  "C1'"  CMP 12 
CMP N9     N9   N 0 1 Y N N 24.303 61.528 3.719 0.309  -0.374 1.600  N9     CMP 13 
CMP C8     C8   C 0 1 Y N N 25.623 61.948 3.754 1.602  0.035  1.728  C8     CMP 14 
CMP N7     N7   N 0 1 Y N N 26.473 61.067 3.259 1.836  0.393  2.958  N7     CMP 15 
CMP C5     C5   C 0 1 Y N N 25.660 59.993 2.899 0.708  0.241  3.693  C5     CMP 16 
CMP C6     C6   C 0 1 Y N N 25.939 58.758 2.334 0.372  0.452  5.041  C6     CMP 17 
CMP N6     N6   N 0 1 N N N 27.173 58.368 2.015 1.309  0.938  5.937  N6     CMP 18 
CMP N1     N1   N 0 1 Y N N 24.912 57.922 2.097 -0.867 0.180  5.434  N1     CMP 19 
CMP C2     C2   C 0 1 Y N N 23.693 58.298 2.413 -1.767 -0.282 4.587  C2     CMP 20 
CMP N3     N3   N 0 1 Y N N 23.282 59.438 2.960 -1.496 -0.501 3.317  N3     CMP 21 
CMP C4     C4   C 0 1 Y N N 24.329 60.259 3.182 -0.282 -0.258 2.833  C4     CMP 22 
CMP HOP2   2HOP H 0 0 N N N 21.400 66.619 6.835 -0.136 0.638  -6.218 HOP2   CMP 23 
CMP "H5'1" 1H5* H 0 0 N N N 22.959 66.534 4.128 2.083  -0.554 -2.726 "H5'1" CMP 24 
CMP "H5'2" 2H5* H 0 0 N N N 24.413 65.707 3.884 1.706  -2.290 -2.899 "H5'2" CMP 25 
CMP "H4'"  H4*  H 0 1 N N N 21.796 64.749 4.871 -0.632 -1.772 -2.084 "H4'"  CMP 26 
CMP "H3'"  H3*  H 0 1 N N N 24.471 63.518 6.123 0.687  0.973  -1.690 "H3'"  CMP 27 
CMP "H2'"  H2*  H 0 1 N N N 23.219 61.440 6.226 -0.776 1.272  0.143  "H2'"  CMP 28 
CMP "HO2'" *HO2 H 0 0 N N N 21.033 61.395 5.635 -2.775 0.159  0.259  "HO2'" CMP 29 
CMP "H1'"  H1*  H 0 1 N N N 22.248 61.623 3.654 -1.104 -1.580 0.616  "H1'"  CMP 30 
CMP H8     H8   H 0 1 N N N 25.973 62.916 4.148 2.327  0.059  0.928  H8     CMP 31 
CMP HN61   1HN6 H 0 0 N N N 27.378 57.459 1.599 1.063  1.083  6.864  HN61   CMP 32 
CMP HN62   2HN6 H 0 0 N N N 27.747 58.456 2.853 2.212  1.129  5.639  HN62   CMP 33 
CMP H2     H2   H 0 1 N N N 22.908 57.556 2.188 -2.763 -0.490 4.948  H2     CMP 34 
# 
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 
CMP P     O1P    DOUB N N 1  
CMP P     O2P    SING N N 2  
CMP P     "O5'"  SING N N 3  
CMP P     "O3'"  SING N N 4  
CMP O2P   HOP2   SING N N 5  
CMP "O5'" "C5'"  SING N N 6  
CMP "C5'" "C4'"  SING N N 7  
CMP "C5'" "H5'1" SING N N 8  
CMP "C5'" "H5'2" SING N N 9  
CMP "C4'" "O4'"  SING N N 10 
CMP "C4'" "C3'"  SING N N 11 
CMP "C4'" "H4'"  SING N N 12 
CMP "O4'" "C1'"  SING N N 13 
CMP "C3'" "O3'"  SING N N 14 
CMP "C3'" "C2'"  SING N N 15 
CMP "C3'" "H3'"  SING N N 16 
CMP "C2'" "O2'"  SING N N 17 
CMP "C2'" "C1'"  SING N N 18 
CMP "C2'" "H2'"  SING N N 19 
CMP "O2'" "HO2'" SING N N 20 
CMP "C1'" N9     SING N N 21 
CMP "C1'" "H1'"  SING N N 22 
CMP N9    C8     SING Y N 23 
CMP N9    C4     SING Y N 24 
CMP C8    N7     DOUB Y N 25 
CMP C8    H8     SING N N 26 
CMP N7    C5     SING Y N 27 
CMP C5    C6     SING Y N 28 
CMP C5    C4     DOUB Y N 29 
CMP C6    N6     SING N N 30 
CMP C6    N1     DOUB Y N 31 
CMP N6    HN61   SING N N 32 
CMP N6    HN62   SING N N 33 
CMP N1    C2     SING Y N 34 
CMP C2    N3     DOUB Y N 35 
CMP C2    H2     SING N N 36 
CMP N3    C4     SING Y N 37 
# 
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 
CMP SMILES           ACDLabs              10.04 "O=P3(OCC4OC(n1c2ncnc(N)c2nc1)C(O)C4O3)O"                                                                                                                
CMP SMILES_CANONICAL CACTVS               3.341 "Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4CO[P@](O)(=O)O[C@H]4[C@H]3O"                                                                                             
CMP SMILES           CACTVS               3.341 "Nc1ncnc2n(cnc12)[CH]3O[CH]4CO[P](O)(=O)O[CH]4[CH]3O"                                                                                                    
CMP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)CO[P@](=O)(O4)O)O)N"                                                                                      
CMP SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C(C4C(O3)COP(=O)(O4)O)O)N"                                                                                                          
CMP InChI            InChI                1.03  "InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1" 
CMP InChIKey         InChI                1.03  IVOMOUWHDPKRLL-KQYNXXCUSA-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 
CMP "SYSTEMATIC NAME" ACDLabs              10.04 "(2R,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide" 
CMP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1R,4R,6S,7R,8R)-8-(6-aminopurin-9-yl)-4-hydroxy-4-oxo-3,5,9-trioxa-4$l^{5}-phosphabicyclo[4.3.0]nonan-7-ol"   
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
CMP "Create component"  1999-07-08 EBI  
CMP "Modify descriptor" 2011-06-04 RCSB 
CMP "Modify synonyms"   2020-05-28 PDBE 
# 
loop_
_pdbx_chem_comp_synonyms.ordinal 
_pdbx_chem_comp_synonyms.comp_id 
_pdbx_chem_comp_synonyms.name 
_pdbx_chem_comp_synonyms.provenance 
_pdbx_chem_comp_synonyms.type 
1 CMP "CYCLIC AMP" ? ? 
2 CMP CAMP         ? ? 
# 
