data_YSA
# 
_chem_comp.id                                    YSA 
_chem_comp.name                                  "5'-O-[N-(L-TYROSYL)SULFAMOYL]ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H23 N7 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         TYROSYLADENYLATE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-03-02 
_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                        509.493 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     YSA 
_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                  PDBJ 
# 
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 
YSA CD1    CD1  C 0 1 Y N N 20.743 166.404 213.881 -5.594 1.011  1.403  CD1    YSA 1  
YSA CE1    CE1  C 0 1 Y N N 19.842 167.461 213.788 -6.250 2.118  1.905  CE1    YSA 2  
YSA CZ     CZ   C 0 1 Y N N 19.033 167.587 212.662 -6.644 3.136  1.049  CZ     YSA 3  
YSA OH     OH   O 0 1 N N N 18.154 168.620 212.563 -7.295 4.224  1.539  OH     YSA 4  
YSA CE2    CE2  C 0 1 Y N N 19.124 166.655 211.632 -6.374 3.042  -0.309 CE2    YSA 5  
YSA CD2    CD2  C 0 1 Y N N 20.025 165.598 211.726 -5.713 1.934  -0.805 CD2    YSA 6  
YSA CG     CG   C 0 1 Y N N 20.837 165.473 212.850 -5.320 0.921  0.051  CG     YSA 7  
YSA CB     CB   C 0 1 N N N 21.875 164.351 212.927 -4.599 -0.285 -0.493 CB     YSA 8  
YSA CA     CA   C 0 1 N N S 21.252 162.954 212.982 -3.091 -0.030 -0.471 CA     YSA 9  
YSA N      N    N 0 1 N N N 20.413 162.838 214.183 -2.766 1.066  -1.395 N      YSA 10 
YSA C      C    C 0 1 N N N 22.383 161.926 213.058 -2.364 -1.279 -0.899 C      YSA 11 
YSA O      O    O 0 1 N N N 22.541 161.235 214.064 -1.951 -1.381 -2.034 O      YSA 12 
YSA NAT    NAT  N 0 1 N N N 23.125 161.826 211.959 -2.173 -2.282 -0.019 NAT    YSA 13 
YSA SBI    SBI  S 0 1 N N N 24.386 160.795 211.899 -1.374 -3.654 -0.488 SBI    YSA 14 
YSA OAD    OAD  O 0 1 N N N 23.950 159.381 212.144 -1.295 -4.471 0.672  OAD    YSA 15 
YSA OAE    OAE  O 0 1 N N N 25.400 161.186 212.933 -1.959 -4.037 -1.726 OAE    YSA 16 
YSA "O5'"  O5*  O 0 1 N N N 25.016 160.893 210.544 0.059  -3.258 -0.814 "O5'"  YSA 17 
YSA "C5'"  C5*  C 0 1 N N N 24.774 159.877 209.570 0.721  -3.041 0.434  "C5'"  YSA 18 
YSA "C4'"  C4*  C 0 1 N N R 23.766 160.347 208.519 2.174  -2.637 0.177  "C4'"  YSA 19 
YSA "O4'"  O4*  O 0 1 N N N 23.936 159.542 207.339 2.218  -1.350 -0.461 "O4'"  YSA 20 
YSA "C3'"  C3*  C 0 1 N N S 22.339 160.094 209.008 2.929  -2.515 1.515  "C3'"  YSA 21 
YSA "O3'"  O3*  O 0 1 N N N 21.391 160.856 208.254 4.029  -3.425 1.561  "O3'"  YSA 22 
YSA "C2'"  C2*  C 0 1 N N R 22.211 158.606 208.694 3.435  -1.049 1.529  "C2'"  YSA 23 
YSA "O2'"  O2*  O 0 1 N N N 20.827 158.262 208.559 4.767  -0.975 2.043  "O2'"  YSA 24 
YSA "C1'"  C1*  C 0 1 N N R 22.931 158.511 207.345 3.402  -0.680 0.024  "C1'"  YSA 25 
YSA N9     N9   N 0 1 Y N N 23.583 157.188 207.190 3.282  0.770  -0.152 N9     YSA 26 
YSA C8     C8   C 0 1 Y N N 24.422 156.653 208.074 2.121  1.477  -0.257 C8     YSA 27 
YSA N7     N7   N 0 1 Y N N 24.850 155.465 207.653 2.383  2.743  -0.404 N7     YSA 28 
YSA C5     C5   C 0 1 Y N N 24.272 155.233 206.480 3.725  2.929  -0.402 C5     YSA 29 
YSA C4     C4   C 0 1 Y N N 23.472 156.329 206.178 4.318  1.666  -0.234 C4     YSA 30 
YSA N3     N3   N 0 1 Y N N 22.780 156.320 205.029 5.643  1.573  -0.205 N3     YSA 31 
YSA C2     C2   C 0 1 Y N N 22.842 155.295 204.194 6.394  2.649  -0.320 C2     YSA 32 
YSA N1     N1   N 0 1 Y N N 23.588 154.235 204.458 5.883  3.856  -0.474 N1     YSA 33 
YSA C6     C6   C 0 1 Y N N 24.313 154.169 205.586 4.568  4.047  -0.520 C6     YSA 34 
YSA N6     N6   N 0 1 N N N 25.052 153.098 205.870 4.042  5.316  -0.681 N6     YSA 35 
YSA HD1    HD1  H 0 1 N N N 21.384 166.304 214.773 -5.287 0.218  2.069  HD1    YSA 36 
YSA HE1    HE1  H 0 1 N N N 19.769 168.198 214.606 -6.459 2.190  2.962  HE1    YSA 37 
YSA HOH    HOH  H 0 1 N N N 17.602 168.706 211.795 -8.240 4.022  1.508  HOH    YSA 38 
YSA HE2    HE2  H 0 1 N N N 18.482 166.754 210.741 -6.680 3.833  -0.977 HE2    YSA 39 
YSA HD2    HD2  H 0 1 N N N 20.096 164.860 210.910 -5.502 1.860  -1.861 HD2    YSA 40 
YSA HB1    1HB  H 0 1 N N N 22.568 164.510 213.786 -4.922 -0.470 -1.518 HB1    YSA 41 
YSA HB2    2HB  H 0 1 N N N 22.604 164.427 212.087 -4.829 -1.154 0.123  HB2    YSA 42 
YSA HA     HA   H 0 1 N N N 20.625 162.778 212.077 -2.783 0.243  0.538  HA     YSA 43 
YSA HN1    1HN  H 0 1 N N N 19.710 163.576 214.235 -3.067 0.771  -2.311 HN1    YSA 44 
YSA HN2    2HN  H 0 1 N N N 19.998 161.907 214.220 -3.350 1.847  -1.135 HN2    YSA 45 
YSA HAT    HAT  H 0 1 N N N 22.769 162.464 211.247 -2.503 -2.200 0.889  HAT    YSA 46 
YSA "H5'1" 1H5* H 0 0 N N N 24.454 158.921 210.046 0.214  -2.246 0.981  "H5'1" YSA 47 
YSA "H5'2" 2H5* H 0 0 N N N 25.722 159.525 209.100 0.697  -3.958 1.022  "H5'2" YSA 48 
YSA "H4'"  H4*  H 0 1 N N N 23.930 161.432 208.323 2.659  -3.381 -0.455 "H4'"  YSA 49 
YSA "H3'"  H3*  H 0 1 N N N 22.151 160.374 210.071 2.252  -2.694 2.352  "H3'"  YSA 50 
YSA H3     H3   H 0 1 N N N 20.505 160.699 208.558 4.495  -3.259 2.392  H3     YSA 51 
YSA "H2'"  H2*  H 0 1 N N N 22.628 157.925 209.472 2.763  -0.410 2.102  "H2'"  YSA 52 
YSA H1     H1   H 0 1 N N N 20.747 157.336 208.364 4.719  -1.216 2.978  H1     YSA 53 
YSA "H1'"  H1*  H 0 1 N N N 22.206 158.635 206.507 4.290  -1.055 -0.483 "H1'"  YSA 54 
YSA H8     H8   H 0 1 N N N 24.721 157.128 209.024 1.130  1.049  -0.224 H8     YSA 55 
YSA H2     H2   H 0 1 N N N 22.259 155.325 203.258 7.468  2.539  -0.288 H2     YSA 56 
YSA HN61   1HN6 H 0 0 N N N 24.772 152.743 206.784 3.080  5.442  -0.714 HN61   YSA 57 
YSA HN62   2HN6 H 0 0 N N N 25.082 152.317 205.214 4.634  6.080  -0.762 HN62   YSA 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 
YSA CD1   CE1    DOUB Y N 1  
YSA CD1   CG     SING Y N 2  
YSA CD1   HD1    SING N N 3  
YSA CE1   CZ     SING Y N 4  
YSA CE1   HE1    SING N N 5  
YSA CZ    OH     SING N N 6  
YSA CZ    CE2    DOUB Y N 7  
YSA OH    HOH    SING N N 8  
YSA CE2   CD2    SING Y N 9  
YSA CE2   HE2    SING N N 10 
YSA CD2   CG     DOUB Y N 11 
YSA CD2   HD2    SING N N 12 
YSA CG    CB     SING N N 13 
YSA CB    CA     SING N N 14 
YSA CB    HB1    SING N N 15 
YSA CB    HB2    SING N N 16 
YSA CA    N      SING N N 17 
YSA CA    C      SING N N 18 
YSA CA    HA     SING N N 19 
YSA N     HN1    SING N N 20 
YSA N     HN2    SING N N 21 
YSA C     O      DOUB N N 22 
YSA C     NAT    SING N N 23 
YSA NAT   SBI    SING N N 24 
YSA NAT   HAT    SING N N 25 
YSA SBI   OAD    DOUB N N 26 
YSA SBI   OAE    DOUB N N 27 
YSA SBI   "O5'"  SING N N 28 
YSA "O5'" "C5'"  SING N N 29 
YSA "C5'" "C4'"  SING N N 30 
YSA "C5'" "H5'1" SING N N 31 
YSA "C5'" "H5'2" SING N N 32 
YSA "C4'" "O4'"  SING N N 33 
YSA "C4'" "C3'"  SING N N 34 
YSA "C4'" "H4'"  SING N N 35 
YSA "O4'" "C1'"  SING N N 36 
YSA "C3'" "O3'"  SING N N 37 
YSA "C3'" "C2'"  SING N N 38 
YSA "C3'" "H3'"  SING N N 39 
YSA "O3'" H3     SING N N 40 
YSA "C2'" "O2'"  SING N N 41 
YSA "C2'" "C1'"  SING N N 42 
YSA "C2'" "H2'"  SING N N 43 
YSA "O2'" H1     SING N N 44 
YSA "C1'" N9     SING N N 45 
YSA "C1'" "H1'"  SING N N 46 
YSA N9    C8     SING Y N 47 
YSA N9    C4     SING Y N 48 
YSA C8    N7     DOUB Y N 49 
YSA C8    H8     SING N N 50 
YSA N7    C5     SING Y N 51 
YSA C5    C4     DOUB Y N 52 
YSA C5    C6     SING Y N 53 
YSA C4    N3     SING Y N 54 
YSA N3    C2     DOUB Y N 55 
YSA C2    N1     SING Y N 56 
YSA C2    H2     SING N N 57 
YSA N1    C6     DOUB Y N 58 
YSA C6    N6     SING N N 59 
YSA N6    HN61   SING N N 60 
YSA N6    HN62   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 
YSA SMILES           ACDLabs              10.04 O=C(NS(=O)(=O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)C(N)Cc4ccc(O)cc4 
YSA InChI            InChI                1.02b 
InChI=1/C19H23N7O8S/c20-11(5-9-1-3-10(27)4-2-9)18(30)25-35(31,32)33-6-12-14(28)15(29)19(34-12)26-8-24-13-16(21)22-7-23-17(13)26/h1-4,7-8,11-12,14-15,19,27-29H,5-6,20H2,(H,25,30)(H2,21,22,23)/t11-,12+,14+,15+,19+/m0/s1/f/h25H,21H2 
YSA InChIKey         InChI                1.02b MJZAZMKENKZBAJ-CNMJOCCEDF 
YSA SMILES_CANONICAL CACTVS               3.341 N[C@@H](Cc1ccc(O)cc1)C(=O)N[S](=O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n3cnc4c(N)ncnc34 
YSA SMILES           CACTVS               3.341 N[CH](Cc1ccc(O)cc1)C(=O)N[S](=O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)n3cnc4c(N)ncnc34 
YSA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C[C@@H](C(=O)NS(=O)(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)n3cnc4c3ncnc4N)O)O)N)O 
YSA SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CC(C(=O)NS(=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 
YSA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-(L-tyrosylsulfamoyl)adenosine"                                                                                           
YSA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl N-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]sulfamate" 
# 
