data_IOT
# 
_chem_comp.id                                    IOT 
_chem_comp.name                                  
;ARGININE-N-METHYLCARBONYL PHOSPHORIC ACID 5'-ADENOSINE ESTER
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H28 N9 O10 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-09-19 
_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                        561.443 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IOT 
_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        1MBZ 
_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 
IOT PA     PA   P 0 1 N N R -2.610  92.609 63.617 0.905  0.516  0.501  PA     IOT 1  
IOT O1A    O1A  O 0 1 N N N -3.108  93.480 62.455 2.239  0.722  1.107  O1A    IOT 2  
IOT O2A    O2A  O 0 1 N N N -1.105  92.634 63.971 0.246  1.943  0.155  O2A    IOT 3  
IOT "O5'"  O5*  O 0 1 N N N -2.885  92.662 65.003 1.057  -0.346 -0.849 "O5'"  IOT 4  
IOT "C5'"  C5*  C 0 1 N N N -4.214  93.158 65.447 1.902  0.402  -1.725 "C5'"  IOT 5  
IOT "C4'"  C4*  C 0 1 N N R -4.736  94.216 66.268 2.088  -0.366 -3.035 "C4'"  IOT 6  
IOT "O4'"  O4*  O 0 1 N N N -4.389  93.747 67.589 0.818  -0.536 -3.686 "O4'"  IOT 7  
IOT "C3'"  C3*  C 0 1 N N S -4.158  95.658 66.143 2.992  0.437  -3.990 "C3'"  IOT 8  
IOT "O3'"  O3*  O 0 1 N N N -4.887  96.634 65.531 4.168  -0.304 -4.319 "O3'"  IOT 9  
IOT "C2'"  C2*  C 0 1 N N R -3.717  95.937 67.571 2.113  0.649  -5.250 "C2'"  IOT 10 
IOT "O2'"  O2*  O 0 1 N N N -4.679  96.885 68.133 2.883  0.483  -6.442 "O2'"  IOT 11 
IOT "C1'"  C1*  C 0 1 N N R -3.726  94.715 68.406 1.063  -0.481 -5.108 "C1'"  IOT 12 
IOT N9     N9   N 0 1 Y N N -2.374  94.363 68.640 -0.166 -0.142 -5.830 N9     IOT 13 
IOT C8     C8   C 0 1 Y N N -1.431  93.736 67.766 -1.204 0.598  -5.351 C8     IOT 14 
IOT N7     N7   N 0 1 Y N N -0.235  93.522 68.267 -2.131 0.703  -6.258 N7     IOT 15 
IOT C5     C5   C 0 1 Y N N -0.313  94.027 69.559 -1.748 0.037  -7.373 C5     IOT 16 
IOT C6     C6   C 0 1 Y N N 0.691   94.100 70.677 -2.323 -0.189 -8.635 C6     IOT 17 
IOT N6     N6   N 0 1 N N N 1.852   93.692 70.596 -3.567 0.328  -8.950 N6     IOT 18 
IOT N1     N1   N 0 1 Y N N 0.165   94.718 71.864 -1.644 -0.912 -9.519 N1     IOT 19 
IOT C2     C2   C 0 1 Y N N -1.174  95.216 72.058 -0.456 -1.410 -9.228 C2     IOT 20 
IOT N3     N3   N 0 1 Y N N -2.094  95.146 71.052 0.120  -1.223 -8.060 N3     IOT 21 
IOT C4     C4   C 0 1 Y N N -1.643  94.544 69.819 -0.480 -0.508 -7.114 C4     IOT 22 
IOT CX     CX   C 0 1 N N N -4.058  89.161 63.170 -1.192 -0.478 3.712  CX     IOT 23 
IOT CW     CW   C 0 1 N N N -3.297  89.978 62.993 -0.308 0.260  2.741  CW     IOT 24 
IOT OX1    OX1  O 0 1 N N N -2.267  89.835 62.106 0.158  1.332  3.044  OX1    IOT 25 
IOT OX2    OX2  O 0 1 N N N -3.085  91.107 63.745 -0.039 -0.273 1.539  OX2    IOT 26 
IOT NX     NX   N 0 1 N N N -5.633  89.774 62.921 -1.331 0.308  4.944  NX     IOT 27 
IOT CA     CA   C 0 1 N N S -6.150  90.000 61.528 -2.199 -0.463 5.843  CA     IOT 28 
IOT CB     CB   C 0 1 N N N -7.210  88.923 61.185 -1.823 -0.165 7.296  CB     IOT 29 
IOT CG     CG   C 0 1 N N N -6.779  87.930 60.143 -0.364 -0.557 7.536  CG     IOT 30 
IOT CD     CD   C 0 1 N N N -7.857  86.938 59.941 0.011  -0.259 8.989  CD     IOT 31 
IOT NE     NE   N 0 1 N N N -8.778  87.319 58.918 1.408  -0.635 9.219  NE     IOT 32 
IOT CZ     CZ   C 0 1 N N N -9.738  86.535 58.448 1.973  -0.457 10.460 CZ     IOT 33 
IOT NH1    NH1  N 0 1 N N N -10.803 86.189 59.173 1.265  0.045  11.432 NH1    IOT 34 
IOT NH2    NH2  N 0 1 N N N -9.609  86.082 57.229 3.284  -0.809 10.675 NH2    IOT 35 
IOT C      C    C 0 1 N N N -6.799  91.390 61.430 -3.636 -0.077 5.607  C      IOT 36 
IOT O      O    O 0 1 N N N -6.814  92.103 62.460 -4.517 -0.884 5.788  O      IOT 37 
IOT OX3    OX3  O 0 1 N N N -7.283  91.759 60.341 -3.939 1.164  5.195  OX3    IOT 38 
IOT HO2    HO2  H 0 1 N N N -0.796  92.095 64.690 -0.618 1.764  -0.236 HO2    IOT 39 
IOT "H5'1" 1H5* H 0 0 N N N -4.749  93.313 64.481 1.443  1.369  -1.933 "H5'1" IOT 40 
IOT "H5'2" 2H5* H 0 0 N N N -4.672  92.249 65.902 2.872  0.554  -1.252 "H5'2" IOT 41 
IOT "H4'"  H4*  H 0 1 N N N -5.802  94.364 65.979 2.535  -1.339 -2.833 "H4'"  IOT 42 
IOT "H3'"  H3*  H 0 1 N N N -3.340  95.692 65.385 3.259  1.396  -3.545 "H3'"  IOT 43 
IOT "HO'3" 3HO* H 0 0 N N N -4.534  97.513 65.454 4.660  0.222  -4.963 "HO'3" IOT 44 
IOT "H2'"  H2*  H 0 1 N N N -2.674  96.331 67.561 1.634  1.629  -5.232 "H2'"  IOT 45 
IOT "HO'2" 2HO* H 0 0 N N N -4.403  97.059 69.025 3.515  1.214  -6.471 "HO'2" IOT 46 
IOT "H1'"  H1*  H 0 1 N N N -4.232  94.816 69.394 1.467  -1.428 -5.465 "H1'"  IOT 47 
IOT H8     H8   H 0 1 N N N -1.622  93.423 66.725 -1.251 1.035  -4.364 H8     IOT 48 
IOT H61    1H6  H 0 1 N N N 2.532   93.741 71.354 -3.953 0.164  -9.825 H61    IOT 49 
IOT H62    2H6  H 0 1 N N N 2.272   94.150 69.787 -4.053 0.854  -8.296 H62    IOT 50 
IOT H2     H2   H 0 1 N N N -1.506  95.666 73.008 0.061  -1.993 -9.976 H2     IOT 51 
IOT HCX1   1HCX H 0 0 N N N -3.856  88.258 62.547 -0.746 -1.445 3.947  HCX1   IOT 52 
IOT HCX2   2HCX H 0 0 N N N -3.944  88.692 64.175 -2.175 -0.630 3.266  HCX2   IOT 53 
IOT HNX    HNX  H 0 1 N N N -5.722  90.646 63.441 -1.838 1.145  4.699  HNX    IOT 54 
IOT HA     HA   H 0 1 N N N -5.298  89.934 60.811 -2.072 -1.527 5.646  HA     IOT 55 
IOT HB1    1HB  H 0 1 N N N -7.539  88.395 62.110 -2.468 -0.738 7.963  HB1    IOT 56 
IOT HB2    2HB  H 0 1 N N N -8.170  89.405 60.886 -1.951 0.899  7.493  HB2    IOT 57 
IOT HG1    1HG  H 0 1 N N N -6.472  88.422 59.190 0.280  0.015  6.869  HG1    IOT 58 
IOT HG2    2HG  H 0 1 N N N -5.804  87.450 60.393 -0.236 -1.621 7.339  HG2    IOT 59 
IOT HD1    1HD  H 0 1 N N N -7.434  85.925 59.740 -0.632 -0.832 9.656  HD1    IOT 60 
IOT HD2    2HD  H 0 1 N N N -8.388  86.726 60.897 -0.115 0.804  9.186  HD2    IOT 61 
IOT HE     HE   H 0 1 N N N -8.224  87.624 58.117 1.935  -1.008 8.495  HE     IOT 62 
IOT HH11   1HH1 H 0 0 N N N -11.439 86.761 58.618 0.339  0.293  11.280 HH11   IOT 63 
IOT HH21   1HH2 H 0 0 N N N -10.347 85.478 56.867 3.682  -0.684 11.551 HH21   IOT 64 
IOT HH22   2HH2 H 0 0 N N N -8.711  85.604 57.140 3.810  -1.187 9.953  HH22   IOT 65 
IOT HX3    HX3  H 0 1 N N N -7.684  92.618 60.280 -4.861 1.411  5.043  HX3    IOT 66 
# 
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 
IOT PA    O1A    DOUB N N 1  
IOT PA    O2A    SING N N 2  
IOT PA    "O5'"  SING N N 3  
IOT PA    OX2    SING N N 4  
IOT O2A   HO2    SING N N 5  
IOT "O5'" "C5'"  SING N N 6  
IOT "C5'" "C4'"  SING N N 7  
IOT "C5'" "H5'1" SING N N 8  
IOT "C5'" "H5'2" SING N N 9  
IOT "C4'" "O4'"  SING N N 10 
IOT "C4'" "C3'"  SING N N 11 
IOT "C4'" "H4'"  SING N N 12 
IOT "O4'" "C1'"  SING N N 13 
IOT "C3'" "O3'"  SING N N 14 
IOT "C3'" "C2'"  SING N N 15 
IOT "C3'" "H3'"  SING N N 16 
IOT "O3'" "HO'3" SING N N 17 
IOT "C2'" "O2'"  SING N N 18 
IOT "C2'" "C1'"  SING N N 19 
IOT "C2'" "H2'"  SING N N 20 
IOT "O2'" "HO'2" SING N N 21 
IOT "C1'" N9     SING N N 22 
IOT "C1'" "H1'"  SING N N 23 
IOT N9    C8     SING Y N 24 
IOT N9    C4     SING Y N 25 
IOT C8    N7     DOUB Y N 26 
IOT C8    H8     SING N N 27 
IOT N7    C5     SING Y N 28 
IOT C5    C6     DOUB Y N 29 
IOT C5    C4     SING Y N 30 
IOT C6    N6     SING N N 31 
IOT C6    N1     SING Y N 32 
IOT N6    H61    SING N N 33 
IOT N6    H62    SING N N 34 
IOT N1    C2     DOUB Y N 35 
IOT C2    N3     SING Y N 36 
IOT C2    H2     SING N N 37 
IOT N3    C4     DOUB Y N 38 
IOT CX    CW     SING N N 39 
IOT CX    NX     SING N N 40 
IOT CX    HCX1   SING N N 41 
IOT CX    HCX2   SING N N 42 
IOT CW    OX1    DOUB N N 43 
IOT CW    OX2    SING N N 44 
IOT NX    CA     SING N N 45 
IOT NX    HNX    SING N N 46 
IOT CA    CB     SING N N 47 
IOT CA    C      SING N N 48 
IOT CA    HA     SING N N 49 
IOT CB    CG     SING N N 50 
IOT CB    HB1    SING N N 51 
IOT CB    HB2    SING N N 52 
IOT CG    CD     SING N N 53 
IOT CG    HG1    SING N N 54 
IOT CG    HG2    SING N N 55 
IOT CD    NE     SING N N 56 
IOT CD    HD1    SING N N 57 
IOT CD    HD2    SING N N 58 
IOT NE    CZ     SING N N 59 
IOT NE    HE     SING N N 60 
IOT CZ    NH1    DOUB N N 61 
IOT CZ    NH2    SING N N 62 
IOT NH1   HH11   SING N N 63 
IOT NH2   HH21   SING N N 64 
IOT NH2   HH22   SING N N 65 
IOT C     O      DOUB N N 66 
IOT C     OX3    SING N N 67 
IOT OX3   HX3    SING N N 68 
# 
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 
IOT SMILES           ACDLabs              10.04 O=C(O)C(NCC(=O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)CCCNC(=[N@H])N 
IOT InChI            InChI                1.02b 
;InChI=1/C18H28N9O10P/c19-14-11-15(25-6-24-14)27(7-26-11)16-13(30)12(29)9(36-16)5-35-38(33,34)37-10(28)4-23-8(17(31)32)2-1-3-22-18(20)21/h6-9,12-13,16,23,29-30H,1-5H2,(H,31,32)(H,33,34)(H2,19,24,25)(H4,20,21,22)/t8-,9+,12+,13+,16+/m0/s1/f/h20,22,31,33H,19,21H2
;
IOT InChIKey         InChI                1.02b PLEMKERVZBXYMR-DSPQGLLBDN 
IOT SMILES_CANONICAL CACTVS               3.341 NC(=N)NCCC[C@H](NCC(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O 
IOT SMILES           CACTVS               3.341 NC(=N)NCCC[CH](NCC(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23)C(O)=O 
IOT 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)CN[C@@H](CCCNC(=N)N)C(=O)O)O)O)N 
IOT SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC(=O)CNC(CCCNC(=N)N)C(=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 
IOT "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,8S)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-8-(3-carbamimidamidopropyl)-3-hydroxy-5-oxo-2,4-dioxa-7-aza-3-phosphanonan-9-oic acid 3-oxide (non-preferred name)" 
IOT "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-2-oxo-ethyl]amino]-5-carbamimidamido-pentanoic acid"                                            
# 
