data_TYA
# 
_chem_comp.id                                    TYA 
_chem_comp.name                                  
;PHOSPHORIC ACID 2-AMINO-3-(4-HYDROXY-PHENYL)-PROPYL ESTER ADENOSIN-5'YL ESTER
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H24 N6 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    -1 
_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                        495.403 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TYA 
_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        3TS1 
_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 
TYA OPP    OPP  O 0  1 N N N -12.327 14.459 -6.988  -2.696  0.578  0.138  OPP    TYA 1  
TYA P      P    P 0  1 N N N -13.255 15.253 -7.946  -1.456  1.300  -0.592 P      TYA 2  
TYA O1P    O1P  O 0  1 N N N -12.653 16.156 -8.950  -1.177  0.605  -1.943 O1P    TYA 3  
TYA O2P    O2P  O -1 1 N N N -13.968 14.465 -8.955  -1.798  2.787  -0.838 O2P    TYA 4  
TYA "O5'"  O5*  O 0  1 N N N -14.260 16.043 -7.037  -0.149  1.198  0.344  "O5'"  TYA 5  
TYA "C5'"  C5*  C 0  1 N N N -15.361 16.739 -7.598  0.879   1.955  -0.299 "C5'"  TYA 6  
TYA "C4'"  C4*  C 0  1 N N R -16.441 16.754 -6.482  2.155   1.899  0.543  "C4'"  TYA 7  
TYA "O4'"  O4*  O 0  1 N N N -17.679 16.671 -7.250  2.674   0.558  0.555  "O4'"  TYA 8  
TYA "C3'"  C3*  C 0  1 N N S -16.433 15.520 -5.573  3.234   2.806  -0.079 "C3'"  TYA 9  
TYA "O3'"  O3*  O 0  1 N N N -17.053 15.700 -4.327  3.629   3.827  0.839  "O3'"  TYA 10 
TYA "C2'"  C2*  C 0  1 N N R -17.238 14.476 -6.364  4.417   1.843  -0.363 "C2'"  TYA 11 
TYA "O2'"  O2*  O 0  1 N N N -17.919 13.588 -5.446  5.664   2.459  -0.036 "O2'"  TYA 12 
TYA "C1'"  C1*  C 0  1 N N R -18.167 15.379 -7.103  4.114   0.664  0.596  "C1'"  TYA 13 
TYA N9     N9   N 0  1 Y N N -18.961 14.930 -8.211  4.736   -0.571 0.113  N9     TYA 14 
TYA C8     C8   C 0  1 Y N N -18.664 14.706 -9.509  4.166   -1.490 -0.717 C8     TYA 15 
TYA N7     N7   N 0  1 Y N N -19.709 14.304 -10.239 5.000   -2.464 -0.941 N7     TYA 16 
TYA C5     C5   C 0  1 Y N N -20.741 14.238 -9.313  6.154   -2.232 -0.271 C5     TYA 17 
TYA C6     C6   C 0  1 Y N N -22.113 13.909 -9.454  7.374   -2.916 -0.139 C6     TYA 18 
TYA N6     N6   N 0  1 N N N -22.699 13.503 -10.582 7.586   -4.119 -0.790 N6     TYA 19 
TYA N1     N1   N 0  1 Y N N -22.863 13.986 -8.319  8.321   -2.381 0.625  N1     TYA 20 
TYA C2     C2   C 0  1 Y N N -22.292 14.424 -7.159  8.128   -1.234 1.249  C2     TYA 21 
TYA N3     N3   N 0  1 Y N N -21.069 14.764 -6.954  7.002   -0.559 1.155  N3     TYA 22 
TYA C4     C4   C 0  1 Y N N -20.321 14.655 -8.085  6.001   -1.013 0.409  C4     TYA 23 
TYA NH2    NH2  N 0  1 N N N -10.524 13.677 -4.976  -5.366  0.795  1.239  NH2    TYA 24 
TYA CA     CA   C 0  1 N N S -11.562 14.685 -4.654  -5.066  0.139  -0.041 CA     TYA 25 
TYA C      C    C 0  1 N N N -12.718 14.502 -5.600  -3.845  0.803  -0.681 C      TYA 26 
TYA CB     CB   C 0  1 N N N -10.944 16.079 -4.715  -6.269  0.272  -0.977 CB     TYA 27 
TYA CG     CG   C 0  1 Y N N -10.308 16.421 -3.507  -7.438  -0.487 -0.404 CG     TYA 28 
TYA CD1    CD1  C 0  1 Y N N -11.052 16.448 -2.337  -8.322  0.148  0.447  CD1    TYA 29 
TYA CD2    CD2  C 0  1 Y N N -8.935  16.743 -3.453  -7.627  -1.816 -0.736 CD2    TYA 30 
TYA CE1    CE1  C 0  1 Y N N -10.456 16.807 -1.126  -9.394  -0.546 0.974  CE1    TYA 31 
TYA CE2    CE2  C 0  1 Y N N -8.331  17.059 -2.230  -8.694  -2.515 -0.208 CE2    TYA 32 
TYA CZ     CZ   C 0  1 Y N N -9.095  17.104 -1.070  -9.583  -1.881 0.647  CZ     TYA 33 
TYA OH     OH   O 0  1 N N N -8.584  17.420 0.142   -10.638 -2.565 1.164  OH     TYA 34 
TYA "H5'1" 1H5* H 0  0 N N N -15.103 17.750 -7.989  1.076   1.535  -1.285 "H5'1" TYA 35 
TYA "H5'2" 2H5* H 0  0 N N N -15.717 16.314 -8.565  0.557   2.991  -0.402 "H5'2" TYA 36 
TYA "H4'"  H4*  H 0  1 N N N -16.291 17.638 -5.820  1.941   2.222  1.562  "H4'"  TYA 37 
TYA "H3'"  H3*  H 0  1 N N N -15.379 15.243 -5.334  2.871   3.248  -1.007 "H3'"  TYA 38 
TYA "HO'3" 3HO* H 0  0 N N N -17.048 14.935 -3.763  4.345   4.321  0.416  "HO'3" TYA 39 
TYA "H2'"  H2*  H 0  1 N N N -16.658 13.793 -7.028  4.409   1.511  -1.402 "H2'"  TYA 40 
TYA "HO'2" 2HO* H 0  0 N N N -18.416 12.942 -5.934  5.793   3.181  -0.667 "HO'2" TYA 41 
TYA "H1'"  H1*  H 0  1 N N N -18.992 15.355 -6.353  4.453   0.894  1.606  "H1'"  TYA 42 
TYA H8     H8   H 0  1 N N N -17.655 14.839 -9.935  3.170   -1.420 -1.128 H8     TYA 43 
TYA H61    1H6  H 0  1 N N N -23.686 13.266 -10.683 6.887   -4.500 -1.346 H61    TYA 44 
TYA H62    2H6  H 0  1 N N N -22.170 12.694 -10.910 8.433   -4.582 -0.691 H62    TYA 45 
TYA H2     H2   H 0  1 N N N -22.911 14.517 -6.251  8.924   -0.835 1.861  H2     TYA 46 
TYA HN1    1HN  H 0  1 N N N -9.740  13.801 -4.334  -5.552  1.764  1.031  HN1    TYA 47 
TYA HN2    2HN  H 0  1 N N N -10.237 13.709 -5.954  -6.231  0.397  1.572  HN2    TYA 48 
TYA HA     HA   H 0  1 N N N -11.955 14.554 -3.619  -4.856  -0.917 0.132  HA     TYA 49 
TYA H1     1H   H 0  1 N N N -13.492 15.286 -5.432  -3.676  0.377  -1.670 H1     TYA 50 
TYA H2A    2H   H 0  1 N N N -13.309 13.596 -5.328  -4.021  1.875  -0.773 H2A    TYA 51 
TYA HB1    1HB  H 0  1 N N N -10.249 16.178 -5.581  -6.534  1.325  -1.080 HB1    TYA 52 
TYA HB2    2HB  H 0  1 N N N -11.698 16.845 -5.007  -6.015  -0.135 -1.956 HB2    TYA 53 
TYA HD1    HD1  H 0  1 N N N -12.122 16.182 -2.369  -8.175  1.188  0.702  HD1    TYA 54 
TYA HD2    HD2  H 0  1 N N N -8.328  16.747 -4.374  -6.935  -2.309 -1.402 HD2    TYA 55 
TYA HE1    HE1  H 0  1 N N N -11.064 16.856 -0.207  -10.085 -0.049 1.640  HE1    TYA 56 
TYA HE2    HE2  H 0  1 N N N -7.250  17.273 -2.180  -8.839  -3.555 -0.464 HE2    TYA 57 
TYA HH     HH   H 0  1 N N N -7.656  17.622 0.180   -11.372 -2.455 0.545  HH     TYA 58 
# 
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 
TYA OPP   P      SING N N 1  
TYA OPP   C      SING N N 2  
TYA P     O1P    DOUB N N 3  
TYA P     O2P    SING N N 4  
TYA P     "O5'"  SING N N 5  
TYA "O5'" "C5'"  SING N N 6  
TYA "C5'" "C4'"  SING N N 7  
TYA "C5'" "H5'1" SING N N 8  
TYA "C5'" "H5'2" SING N N 9  
TYA "C4'" "O4'"  SING N N 10 
TYA "C4'" "C3'"  SING N N 11 
TYA "C4'" "H4'"  SING N N 12 
TYA "O4'" "C1'"  SING N N 13 
TYA "C3'" "O3'"  SING N N 14 
TYA "C3'" "C2'"  SING N N 15 
TYA "C3'" "H3'"  SING N N 16 
TYA "O3'" "HO'3" SING N N 17 
TYA "C2'" "O2'"  SING N N 18 
TYA "C2'" "C1'"  SING N N 19 
TYA "C2'" "H2'"  SING N N 20 
TYA "O2'" "HO'2" SING N N 21 
TYA "C1'" N9     SING N N 22 
TYA "C1'" "H1'"  SING N N 23 
TYA N9    C8     SING Y N 24 
TYA N9    C4     SING Y N 25 
TYA C8    N7     DOUB Y N 26 
TYA C8    H8     SING N N 27 
TYA N7    C5     SING Y N 28 
TYA C5    C6     SING Y N 29 
TYA C5    C4     DOUB Y N 30 
TYA C6    N6     SING N N 31 
TYA C6    N1     DOUB Y N 32 
TYA N6    H61    SING N N 33 
TYA N6    H62    SING N N 34 
TYA N1    C2     SING Y N 35 
TYA C2    N3     DOUB Y N 36 
TYA C2    H2     SING N N 37 
TYA N3    C4     SING Y N 38 
TYA NH2   CA     SING N N 39 
TYA NH2   HN1    SING N N 40 
TYA NH2   HN2    SING N N 41 
TYA CA    C      SING N N 42 
TYA CA    CB     SING N N 43 
TYA CA    HA     SING N N 44 
TYA C     H1     SING N N 45 
TYA C     H2A    SING N N 46 
TYA CB    CG     SING N N 47 
TYA CB    HB1    SING N N 48 
TYA CB    HB2    SING N N 49 
TYA CG    CD1    DOUB Y N 50 
TYA CG    CD2    SING Y N 51 
TYA CD1   CE1    SING Y N 52 
TYA CD1   HD1    SING N N 53 
TYA CD2   CE2    DOUB Y N 54 
TYA CD2   HD2    SING N N 55 
TYA CE1   CZ     DOUB Y N 56 
TYA CE1   HE1    SING N N 57 
TYA CE2   CZ     SING Y N 58 
TYA CE2   HE2    SING N N 59 
TYA CZ    OH     SING N N 60 
TYA OH    HH     SING N N 61 
# 
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 
TYA SMILES           ACDLabs              10.04 [O-]P(=O)(OCC(N)Cc1ccc(O)cc1)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4O 
TYA InChI            InChI                1.02b 
InChI=1/C19H25N6O8P/c20-11(5-10-1-3-12(26)4-2-10)6-31-34(29,30)32-7-13-15(27)16(28)19(33-13)25-9-24-14-17(21)22-8-23-18(14)25/h1-4,8-9,11,13,15-16,19,26-28H,5-7,20H2,(H,29,30)(H2,21,22,23)/p-1/t11-,13+,15+,16+,19+/m0/s1/fC19H24N6O8P/h21H2/q-1 
TYA InChIKey         InChI                1.02b JJLCVHBFTXDJMM-FUYXOOFTDN 
TYA SMILES_CANONICAL CACTVS               3.341 N[C@H](CO[P]([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)Cc4ccc(O)cc4 
TYA SMILES           CACTVS               3.341 N[CH](CO[P]([O-])(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23)Cc4ccc(O)cc4 
TYA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C[C@@H](CO[P@@](=O)([O-])OC[C@@H]2[C@H]([C@H]([C@@H](O2)n3cnc4c3ncnc4N)O)O)N)O 
TYA SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CC(COP(=O)([O-])OCC2C(C(C(O2)n3cnc4c3ncnc4N)O)O)N)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 
TYA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-({[(2S)-2-amino-3-(4-hydroxyphenyl)propyl]oxy}phosphinato)adenosine"                                                 
TYA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S)-2-amino-3-(4-hydroxyphenyl)propyl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl phosphate" 
# 
