data_N5P
# 
_chem_comp.id                                    N5P 
_chem_comp.name                                  1-{2-DEOXY-5-O-[(R)-HYDROXY{[(R)-HYDROXY(PHOSPHONOOXY)PHOSPHORYL]OXY}PHOSPHORYL]-BETA-D-ERYTHRO-PENTOFURANOSYL}-5-NITRO-1H-INDOLE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H17 N2 O14 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "5-NITRO-1-INDOLYL-2'-DEOXYRIBOSIDE-5'-TRIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-03-21 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        518.200 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     N5P 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye OEToolkits" 
_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 
N5P OR2    OR2  O 0  1 N N N -11.998 65.837 38.494 2.199  6.489  4.264  OR2    N5P 1  
N5P NRO    NRO  N 1  1 N N N -12.083 64.841 39.197 1.888  6.522  3.049  NRO    N5P 2  
N5P OR1    OR1  O -1 1 N N N -11.065 64.372 39.684 1.577  7.590  2.470  OR1    N5P 3  
N5P CZ3    CZ3  C 0  1 N N N -13.379 64.215 39.448 1.888  5.311  2.306  CZ3    N5P 4  
N5P CE3    CE3  C 0  1 N N N -13.435 63.087 40.255 1.543  5.334  0.950  CE3    N5P 5  
N5P CD2    CD2  C 0  1 N N N -14.689 62.505 40.486 1.545  4.128  0.220  CD2    N5P 6  
N5P CH2    CH2  C 0  1 N N N -14.522 64.788 38.877 2.232  4.116  2.935  CH2    N5P 7  
N5P CZ2    CZ2  C 0  1 N N N -15.762 64.242 39.088 2.241  2.908  2.231  CZ2    N5P 8  
N5P CE2    CE2  C 0  1 N N N -15.834 63.091 39.891 1.893  2.946  0.876  CE2    N5P 9  
N5P NE1    NE1  N 0  1 N N N -16.913 62.339 40.275 1.818  1.923  -0.049 NE1    N5P 10 
N5P CD1    CD1  C 0  1 N N N -16.491 61.309 41.080 1.433  2.429  -1.266 CD1    N5P 11 
N5P CG     CG   C 0  1 N N N -15.136 61.368 41.238 1.257  3.787  -1.131 CG     N5P 12 
N5P "C1'"  C1*  C 0  1 N N N -18.346 62.553 39.911 2.101  0.516  0.211  "C1'"  N5P 13 
N5P "O4'"  O4*  O 0  1 N N N -19.140 61.497 40.459 2.678  -0.093 -0.958 "O4'"  N5P 14 
N5P "C4'"  C4*  C 0  1 N N N -19.839 60.808 39.424 2.156  -1.432 -1.088 "C4'"  N5P 15 
N5P "C3'"  C3*  C 0  1 N N N -19.933 61.809 38.279 1.309  -1.697 0.152  "C3'"  N5P 16 
N5P "O3'"  O3*  O 0  1 N N N -21.050 62.687 38.470 2.127  -2.250 1.180  "O3'"  N5P 17 
N5P "C2'"  C2*  C 0  1 N N N -18.617 62.561 38.407 0.878  -0.312 0.578  "C2'"  N5P 18 
N5P "C5'"  C5*  C 0  1 N N N -19.116 59.497 39.113 1.348  -1.500 -2.377 "C5'"  N5P 19 
N5P "O5'"  O5*  O 0  1 N N N -19.882 58.704 38.212 2.205  -1.233 -3.474 "O5'"  N5P 20 
N5P PA     PA   P 0  1 N N N -19.480 57.178 37.897 1.615  -1.238 -4.980 PA     N5P 21 
N5P O1A    O1A  O 0  1 N N N -18.003 57.138 37.578 2.616  -0.942 -6.059 O1A    N5P 22 
N5P O2A    O2A  O 0  1 N N N -20.008 56.330 39.030 0.878  -2.671 -5.128 O2A    N5P 23 
N5P O3A    O3A  O 0  1 N N N -20.269 56.735 36.564 0.390  -0.188 -4.892 O3A    N5P 24 
N5P PB     PB   P 0  1 N N N -21.441 57.639 35.922 -0.736 0.231  -5.970 PB     N5P 25 
N5P O1B    O1B  O 0  1 N N N -20.892 58.294 34.677 -1.621 -0.882 -6.449 O1B    N5P 26 
N5P O2B    O2B  O 0  1 N N N -22.078 58.503 36.990 0.090  0.989  -7.134 O2B    N5P 27 
N5P O3B    O3B  O 0  1 N N N -22.512 56.523 35.471 -1.500 1.425  -5.195 O3B    N5P 28 
N5P PG     PG   P 0  1 N N N -23.685 56.000 36.449 -2.396 1.438  -3.851 PG     N5P 29 
N5P O3G    O3G  O 0  1 N N N -23.759 54.517 36.153 -3.703 0.578  -4.258 O3G    N5P 30 
N5P O2G    O2G  O 0  1 N N N -23.229 56.314 37.860 -2.948 2.956  -3.793 O2G    N5P 31 
N5P O1G    O1G  O 0  1 N N N -24.900 56.779 35.998 -1.680 0.973  -2.617 O1G    N5P 32 
N5P HE3    HE3  H 0  1 N N N -12.539 62.670 40.692 1.274  6.266  0.460  HE3    N5P 33 
N5P HH2    HH2  H 0  1 N N N -14.426 65.671 38.263 2.499  4.107  3.990  HH2    N5P 34 
N5P HZ2    HZ2  H 0  1 N N N -16.649 64.680 38.654 2.510  1.980  2.725  HZ2    N5P 35 
N5P HD1    HD1  H 0  1 N N N -17.135 60.563 41.522 1.317  1.781  -2.124 HD1    N5P 36 
N5P HG     HG   H 0  1 N N N -14.522 60.692 41.815 0.954  4.461  -1.920 HG     N5P 37 
N5P "H1'"  H1*  H 0  1 N N N -18.602 63.544 40.315 2.853  0.503  1.007  "H1'"  N5P 38 
N5P "H4'"  H4*  H 0  1 N N N -20.859 60.488 39.683 3.008  -2.117 -1.157 "H4'"  N5P 39 
N5P "H3'"  H3*  H 0  1 N N N -20.084 61.350 37.291 0.475  -2.383 -0.018 "H3'"  N5P 40 
N5P "HO3'" HO3* H 0  0 N N N -21.146 62.881 39.395 2.815  -2.768 0.736  "HO3'" N5P 41 
N5P "H2'1" 1H2* H 0  0 N N N -18.699 63.586 38.017 0.008  0.008  -0.009 "H2'1" N5P 42 
N5P "H2'2" 2H2* H 0  0 N N N -17.805 62.100 37.826 0.635  -0.225 1.641  "H2'2" N5P 43 
N5P "H5'1" 1H5* H 0  0 N N N -18.142 59.723 38.655 0.546  -0.756 -2.367 "H5'1" N5P 44 
N5P "H5'2" 2H5* H 0  0 N N N -18.977 58.937 40.050 0.912  -2.496 -2.504 "H5'2" N5P 45 
N5P HO2A   HO2A H 0  0 N N N -20.119 55.435 38.731 0.529  -2.936 -6.005 HO2A   N5P 46 
N5P HO2B   HO2B H 0  0 N N N -22.211 57.988 37.777 -0.388 1.290  -7.936 HO2B   N5P 47 
N5P HOG3   3HOG H 0  0 N N N -23.774 54.382 35.213 -4.370 0.373  -3.569 HOG3   N5P 48 
N5P HOG2   2HOG H 0  0 N N N -22.281 56.380 37.880 -3.455 3.248  -3.006 HOG2   N5P 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 
N5P OR2   NRO    DOUB N N 1  
N5P NRO   CZ3    SING N N 2  
N5P NRO   OR1    SING N N 3  
N5P CZ3   CH2    SING N N 4  
N5P CZ3   CE3    DOUB N N 5  
N5P CE3   CD2    SING N N 6  
N5P CE3   HE3    SING N N 7  
N5P CD2   CE2    DOUB N N 8  
N5P CD2   CG     SING N N 9  
N5P CH2   CZ2    DOUB N N 10 
N5P CH2   HH2    SING N N 11 
N5P CZ2   CE2    SING N N 12 
N5P CZ2   HZ2    SING N N 13 
N5P CE2   NE1    SING N N 14 
N5P NE1   "C1'"  SING N N 15 
N5P NE1   CD1    SING N N 16 
N5P CD1   CG     DOUB N N 17 
N5P CD1   HD1    SING N N 18 
N5P CG    HG     SING N N 19 
N5P "C1'" "C2'"  SING N N 20 
N5P "C1'" "O4'"  SING N N 21 
N5P "C1'" "H1'"  SING N N 22 
N5P "O4'" "C4'"  SING N N 23 
N5P "C4'" "C3'"  SING N N 24 
N5P "C4'" "C5'"  SING N N 25 
N5P "C4'" "H4'"  SING N N 26 
N5P "C3'" "C2'"  SING N N 27 
N5P "C3'" "O3'"  SING N N 28 
N5P "C3'" "H3'"  SING N N 29 
N5P "O3'" "HO3'" SING N N 30 
N5P "C2'" "H2'1" SING N N 31 
N5P "C2'" "H2'2" SING N N 32 
N5P "C5'" "O5'"  SING N N 33 
N5P "C5'" "H5'1" SING N N 34 
N5P "C5'" "H5'2" SING N N 35 
N5P "O5'" PA     SING N N 36 
N5P PA    O3A    SING N N 37 
N5P PA    O1A    DOUB N N 38 
N5P PA    O2A    SING N N 39 
N5P O2A   HO2A   SING N N 40 
N5P O3A   PB     SING N N 41 
N5P PB    O1B    DOUB N N 42 
N5P PB    O3B    SING N N 43 
N5P PB    O2B    SING N N 44 
N5P O2B   HO2B   SING N N 45 
N5P O3B   PG     SING N N 46 
N5P PG    O1G    DOUB N N 47 
N5P PG    O3G    SING N N 48 
N5P PG    O2G    SING N N 49 
N5P O3G   HOG3   SING N N 50 
N5P O2G   HOG2   SING 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 
N5P SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OP(=O)(O)OCC3OC(n2ccc1cc([N+]([O-])=O)ccc12)CC3O                                                                                                                                            
N5P InChI            InChI                1.02b InChI=1/C13H17N2O14P3/c16-11-6-13(14-4-3-8-5-9(15(17)18)1-2-10(8)14)27-12(11)7-26-31(22,23)29-32(24,25)28-30(19,20)21/h1-5,11-13,16H,6-7H2,(H,22,23)(H,24,25)(H2,19,20,21)/t11-,12+,13+/m0/s1/f/h19-20,22,24H 
N5P InChIKey         InChI                1.02b JJJBDAFRCKSXDR-NBADVHSBDY                                                                                                                                                                                     
N5P SMILES_CANONICAL CACTVS               3.341 O[C@H]1C[C@@H](O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)O[P](O)(O)=O)n2ccc3cc(ccc23)[N+]([O-])=O                                                                                                                     
N5P SMILES           CACTVS               3.341 O[CH]1C[CH](O[CH]1CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)n2ccc3cc(ccc23)[N+]([O-])=O                                                                                                                             
N5P SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(ccn2[C@H]3C[C@@H]([C@H](O3)CO[P@@](=O)(O)O[P@](=O)(O)OP(=O)(O)O)O)cc1[N+](=O)[O-]                                                                                                                      
N5P SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(ccn2C3CC(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)cc1[N+](=O)[O-]                                                                                                                                          
# 
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 
N5P "SYSTEMATIC NAME" ACDLabs              10.04 1-{2-deoxy-5-O-[(R)-hydroxy{[(R)-hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl]-beta-D-erythro-pentofuranosyl}-5-nitro-1H-indole 
N5P "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-3-hydroxy-5-(5-nitroindol-1-yl)oxolan-2-yl]methyl (hydroxy-phosphonooxy-phosphoryl) hydrogen phosphate"              
# 
