data_AMD
# 
_chem_comp.id                                    AMD 
_chem_comp.name                                  "ASPARTYL-2'-DEOXY-ADENOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H19 N6 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               A 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-20 
_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                        446.309 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AMD 
_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                  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 
AMD P      P    P 0 1 N N S 53.517 39.440 -13.211 2.504  1.434  0.332  P      AMD 1  
AMD O1P    O1P  O 0 1 N N N 52.787 38.085 -13.327 2.229  1.011  1.723  O1P    AMD 2  
AMD O2P    O2P  O 0 1 N N N 54.708 39.733 -14.148 3.014  2.961  0.325  O2P    AMD 3  
AMD O3P    O3P  O 0 1 N N N 52.572 40.559 -14.041 3.639  0.485  -0.303 O3P    AMD 4  
AMD "O5'"  O5*  O 0 1 N N N 54.002 39.699 -11.687 1.156  1.315  -0.541 "O5'"  AMD 5  
AMD "C5'"  C5*  C 0 1 N N N 55.003 40.711 -11.387 0.157  2.081  0.135  "C5'"  AMD 6  
AMD "C4'"  C4*  C 0 1 N N R 56.141 40.126 -10.574 -1.156 2.010  -0.647 "C4'"  AMD 7  
AMD "O4'"  O4*  O 0 1 N N N 55.653 39.739 -9.265  -1.713 0.679  -0.586 "O4'"  AMD 8  
AMD "C1'"  C1*  C 0 1 N N R 56.377 38.615 -8.797  -3.116 0.798  -0.872 "C1'"  AMD 9  
AMD N9     N9   N 0 1 Y N N 55.417 37.574 -8.439  -3.867 -0.197 -0.102 N9     AMD 10 
AMD C4     C4   C 0 1 Y N N 55.316 36.921 -7.233  -5.108 -0.695 -0.411 C4     AMD 11 
AMD N3     N3   N 0 1 Y N N 56.076 37.094 -6.141  -5.977 -0.504 -1.398 N3     AMD 12 
AMD C2     C2   C 0 1 Y N N 55.674 36.291 -5.149  -7.120 -1.157 -1.422 C2     AMD 13 
AMD N1     N1   N 0 1 Y N N 54.672 35.412 -5.126  -7.458 -2.027 -0.488 N1     AMD 14 
AMD C6     C6   C 0 1 Y N N 53.914 35.273 -6.242  -6.651 -2.288 0.535  C6     AMD 15 
AMD N6     N6   N 0 1 N N N 52.878 34.424 -6.219  -7.015 -3.201 1.509  N6     AMD 16 
AMD C5     C5   C 0 1 Y N N 54.251 36.051 -7.366  -5.419 -1.616 0.604  C5     AMD 17 
AMD N7     N7   N 0 1 Y N N 53.698 36.144 -8.634  -4.376 -1.625 1.469  N7     AMD 18 
AMD C8     C8   C 0 1 Y N N 54.424 37.056 -9.229  -3.465 -0.793 1.056  C8     AMD 19 
AMD "C2'"  C2*  C 0 1 N N N 57.382 38.223 -9.881  -3.549 2.219  -0.461 "C2'"  AMD 20 
AMD "C3'"  C3*  C 0 1 N N S 56.760 38.850 -11.122 -2.240 2.890  0.025  "C3'"  AMD 21 
AMD "O3'"  O3*  O 0 1 N N N 57.754 39.089 -12.112 -2.161 4.243  -0.429 "O3'"  AMD 22 
AMD N      N    N 0 1 N N N 50.103 42.877 -14.628 7.194  -0.176 0.280  N      AMD 23 
AMD CA     CA   C 0 1 N N S 51.406 42.217 -14.832 5.884  -0.542 -0.276 CA     AMD 24 
AMD CB     CB   C 0 1 N N N 52.539 43.250 -14.887 5.577  -2.002 0.062  CB     AMD 25 
AMD CG     CG   C 0 1 N N N 52.486 44.101 -16.139 6.569  -2.899 -0.633 CG     AMD 26 
AMD OD1    OD1  O 0 1 N N N 52.755 45.320 -16.050 7.433  -2.419 -1.328 OD1    AMD 27 
AMD OD2    OD2  O 0 1 N N N 52.137 43.557 -17.207 6.492  -4.230 -0.481 OD2    AMD 28 
AMD C      C    C 0 1 N N N 51.671 41.220 -13.715 4.821  0.345  0.318  C      AMD 29 
AMD O      O    O 0 1 N N N 50.943 41.144 -12.725 5.032  0.931  1.354  O      AMD 30 
AMD HOP2   2HOP H 0 0 N N N 55.157 40.567 -14.076 3.181  3.196  -0.598 HOP2   AMD 31 
AMD "H5'1" 1H5* H 0 0 N N N 55.373 41.210 -12.312 0.006  1.679  1.136  "H5'1" AMD 32 
AMD "H5'2" 2H5* H 0 0 N N N 54.552 41.598 -10.884 0.482  3.119  0.206  "H5'2" AMD 33 
AMD "H4'"  H4*  H 0 1 N N N 56.906 40.936 -10.581 -1.002 2.314  -1.682 "H4'"  AMD 34 
AMD "H1'"  H1*  H 0 1 N N N 56.970 38.818 -7.875  -3.291 0.650  -1.938 "H1'"  AMD 35 
AMD H2     H2   H 0 1 N N N 56.253 36.364 -4.213  -7.805 -0.975 -2.236 H2     AMD 36 
AMD H61    1H6  H 0 1 N N N 52.307 34.319 -7.058  -6.417 -3.383 2.251  H61    AMD 37 
AMD H62    2H6  H 0 1 N N N 52.270 34.667 -5.436  -7.868 -3.660 1.450  H62    AMD 38 
AMD H8     H8   H 0 1 N N N 54.222 37.352 -10.272 -2.527 -0.603 1.557  H8     AMD 39 
AMD "H2'1" 1H2* H 0 0 N N N 58.438 38.520 -9.678  -3.955 2.756  -1.318 "H2'1" AMD 40 
AMD "H2'2" 2H2* H 0 0 N N N 57.595 37.131 -9.957  -4.281 2.176  0.345  "H2'2" AMD 41 
AMD "H3'"  H3*  H 0 1 N N N 56.007 38.209 -11.637 -2.158 2.842  1.111  "H3'"  AMD 42 
AMD "HO'3" 3HO* H 0 0 N N N 58.140 38.291 -12.454 -2.916 4.711  -0.046 "HO'3" AMD 43 
AMD H      H    H 0 1 N N N 49.349 42.190 -14.591 7.133  -0.309 1.278  H      AMD 44 
AMD HN2    HN2  H 0 1 N N N 49.927 43.591 -15.334 7.855  -0.858 -0.063 HN2    AMD 45 
AMD HA     HA   H 0 1 N N N 51.371 41.675 -15.806 5.900  -0.415 -1.358 HA     AMD 46 
AMD HB1    1HB  H 0 1 N N N 52.548 43.884 -13.970 5.648  -2.149 1.140  HB1    AMD 47 
AMD HB2    2HB  H 0 1 N N N 53.534 42.760 -14.776 4.569  -2.248 -0.272 HB2    AMD 48 
AMD HD2    HD2  H 0 1 N N N 52.103 44.090 -17.992 7.129  -4.805 -0.927 HD2    AMD 49 
# 
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 
AMD P     O1P    DOUB N N 1  
AMD P     O2P    SING N N 2  
AMD P     O3P    SING N N 3  
AMD P     "O5'"  SING N N 4  
AMD O2P   HOP2   SING N N 5  
AMD O3P   C      SING N N 6  
AMD "O5'" "C5'"  SING N N 7  
AMD "C5'" "C4'"  SING N N 8  
AMD "C5'" "H5'1" SING N N 9  
AMD "C5'" "H5'2" SING N N 10 
AMD "C4'" "O4'"  SING N N 11 
AMD "C4'" "C3'"  SING N N 12 
AMD "C4'" "H4'"  SING N N 13 
AMD "O4'" "C1'"  SING N N 14 
AMD "C1'" N9     SING N N 15 
AMD "C1'" "C2'"  SING N N 16 
AMD "C1'" "H1'"  SING N N 17 
AMD N9    C4     SING Y N 18 
AMD N9    C8     SING Y N 19 
AMD C4    N3     SING Y N 20 
AMD C4    C5     DOUB Y N 21 
AMD N3    C2     DOUB Y N 22 
AMD C2    N1     SING Y N 23 
AMD C2    H2     SING N N 24 
AMD N1    C6     DOUB Y N 25 
AMD C6    N6     SING N N 26 
AMD C6    C5     SING Y N 27 
AMD N6    H61    SING N N 28 
AMD N6    H62    SING N N 29 
AMD C5    N7     SING Y N 30 
AMD N7    C8     DOUB Y N 31 
AMD C8    H8     SING N N 32 
AMD "C2'" "C3'"  SING N N 33 
AMD "C2'" "H2'1" SING N N 34 
AMD "C2'" "H2'2" SING N N 35 
AMD "C3'" "O3'"  SING N N 36 
AMD "C3'" "H3'"  SING N N 37 
AMD "O3'" "HO'3" SING N N 38 
AMD N     CA     SING N N 39 
AMD N     H      SING N N 40 
AMD N     HN2    SING N N 41 
AMD CA    CB     SING N N 42 
AMD CA    C      SING N N 43 
AMD CA    HA     SING N N 44 
AMD CB    CG     SING N N 45 
AMD CB    HB1    SING N N 46 
AMD CB    HB2    SING N N 47 
AMD CG    OD1    DOUB N N 48 
AMD CG    OD2    SING N N 49 
AMD OD2   HD2    SING N N 50 
AMD C     O      DOUB N N 51 
# 
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 
AMD SMILES           ACDLabs              10.04 O=C(O)CC(N)C(=O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)CC3O                                                                                                                                             
AMD InChI            InChI                1.02b InChI=1/C14H19N6O9P/c15-6(1-10(22)23)14(24)29-30(25,26)27-3-8-7(21)2-9(28-8)20-5-19-11-12(16)17-4-18-13(11)20/h4-9,21H,1-3,15H2,(H,22,23)(H,25,26)(H2,16,17,18)/t6-,7-,8+,9+/m0/s1/f/h22,25H,16H2 
AMD InChIKey         InChI                1.02b HIZUKUAUIJEUGQ-DALBOKBEDX                                                                                                                                                                         
AMD SMILES_CANONICAL CACTVS               3.341 N[C@@H](CC(O)=O)C(=O)O[P@](O)(=O)OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3c(N)ncnc23                                                                                                                        
AMD SMILES           CACTVS               3.341 N[CH](CC(O)=O)C(=O)O[P](O)(=O)OC[CH]1O[CH](C[CH]1O)n2cnc3c(N)ncnc23                                                                                                                               
AMD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)CO[P@](=O)(O)OC(=O)[C@H](CC(=O)O)N)O)N                                                                                                                   
AMD SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3CC(C(O3)COP(=O)(O)OC(=O)C(CC(=O)O)N)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 
AMD "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(2S)-2-amino-3-carboxypropanoyl]oxy}(hydroxy)phosphoryl]-2'-deoxyadenosine"                                     
AMD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3S)-3-amino-4-[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-oxo-butanoic acid" 
# 
