data_QSI
# 
_chem_comp.id                                    QSI 
_chem_comp.name                                  "5'-O-[N-(L-GLUTAMINYL)-SULFAMOYL]ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H22 N8 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_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                        474.449 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     QSI 
_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        1EUY 
_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 
QSI N      N      N 0 1 N N N 46.116 31.981 13.751 2.245  -0.513 -2.782 N      QSI 1  
QSI CA     CA     C 0 1 N N S 45.204 32.018 14.722 1.131  0.183  -3.439 CA     QSI 2  
QSI CB     CB     C 0 1 N N N 43.876 32.516 14.169 1.261  0.036  -4.956 CB     QSI 3  
QSI CG     CG     C 0 1 N N N 43.132 33.453 15.100 2.587  0.647  -5.416 CG     QSI 4  
QSI CD     CD     C 0 1 N N N 41.791 33.902 14.528 2.715  0.502  -6.910 CD     QSI 5  
QSI OE1    OE1    O 0 1 N N N 40.972 33.087 14.107 1.833  -0.035 -7.545 OE1    QSI 6  
QSI NE2    NE2    N 0 1 N N N 41.523 35.342 14.548 3.810  0.971  -7.541 NE2    QSI 7  
QSI C      C      C 0 1 N N N 45.034 30.635 15.371 -0.173 -0.417 -2.986 C      QSI 8  
QSI O      O      O 0 1 N N N 44.472 30.545 16.479 -0.226 -1.588 -2.673 O      QSI 9  
QSI N10    N10    N 0 1 N N N 45.819 29.550 14.886 -1.282 0.345  -2.928 N10    QSI 10 
QSI S      S      S 0 1 N N N 45.353 27.959 15.156 -2.717 -0.314 -2.430 S      QSI 11 
QSI O1S    O1S    O 0 1 N N N 45.658 27.625 16.585 -3.624 0.773  -2.316 O1S    QSI 12 
QSI O2S    O2S    O 0 1 N N N 45.945 27.194 14.123 -2.913 -1.467 -3.239 O2S    QSI 13 
QSI "O5'"  "O5'"  O 0 1 N N N 43.857 27.824 15.009 -2.513 -0.833 -1.014 "O5'"  QSI 14 
QSI "C5'"  "C5'"  C 0 1 N N N 43.175 28.245 13.821 -2.842 0.239  -0.130 "C5'"  QSI 15 
QSI "C4'"  "C4'"  C 0 1 N N R 41.712 28.442 14.119 -2.657 -0.217 1.317  "C4'"  QSI 16 
QSI "O4'"  "O4'"  O 0 1 N N N 41.135 27.173 14.520 -1.283 -0.570 1.546  "O4'"  QSI 17 
QSI "C1'"  "C1'"  C 0 1 N N R 40.049 27.402 15.409 -0.975 -0.207 2.909  "C1'"  QSI 18 
QSI N9     N9     N 0 1 Y N N 40.237 26.605 16.625 0.469  -0.052 3.089  N9     QSI 19 
QSI C4     C4     C 0 1 Y N N 39.227 26.098 17.413 1.169  -0.250 4.252  C4     QSI 20 
QSI N3     N3     N 0 1 Y N N 37.901 26.259 17.245 0.850  -0.620 5.488  N3     QSI 21 
QSI C2     C2     C 0 1 Y N N 37.220 25.606 18.188 1.777  -0.731 6.416  C2     QSI 22 
QSI N1     N1     N 0 1 Y N N 37.679 24.872 19.207 3.053  -0.490 6.175  N1     QSI 23 
QSI C6     C6     C 0 1 Y N N 39.018 24.737 19.361 3.468  -0.120 4.968  C6     QSI 24 
QSI N6     N6     N 0 1 N N N 39.472 24.013 20.402 4.807  0.130  4.726  N6     QSI 25 
QSI C5     C5     C 0 1 Y N N 39.854 25.377 18.416 2.515  0.011  3.944  C5     QSI 26 
QSI N7     N7     N 0 1 Y N N 41.232 25.440 18.274 2.565  0.358  2.635  N7     QSI 27 
QSI C8     C8     C 0 1 Y N N 41.407 26.189 17.207 1.365  0.320  2.131  C8     QSI 28 
QSI "C2'"  "C2'"  C 0 1 N N R 39.977 28.911 15.647 -1.701 1.149  3.094  "C2'"  QSI 29 
QSI "O2'"  "O2'"  O 0 1 N N N 39.035 29.488 14.756 -1.996 1.386  4.472  "O2'"  QSI 30 
QSI "C3'"  "C3'"  C 0 1 N N S 41.400 29.331 15.311 -3.003 0.935  2.279  "C3'"  QSI 31 
QSI "O3'"  "O3'"  O 0 1 N N N 41.433 30.705 14.964 -4.080 0.568  3.144  "O3'"  QSI 32 
QSI HN1    1HN    H 0 1 N N N 47.005 31.647 14.121 3.095  -0.151 -3.190 HN1    QSI 33 
QSI HN2    2HN    H 0 1 N N N 46.210 32.881 13.280 2.182  -1.482 -3.056 HN2    QSI 34 
QSI HA     HA     H 0 1 N N N 45.555 32.724 15.509 1.157  1.240  -3.172 HA     QSI 35 
QSI HB1    1HB    H 0 1 N N N 44.021 32.990 13.170 1.236  -1.019 -5.222 HB1    QSI 36 
QSI HB2    2HB    H 0 1 N N N 43.227 31.657 13.877 0.435  0.554  -5.443 HB2    QSI 37 
QSI HG1    1HG    H 0 1 N N N 43.005 32.997 16.109 2.612  1.703  -5.149 HG1    QSI 38 
QSI HG2    2HG    H 0 1 N N N 43.763 34.329 15.376 3.414  0.129  -4.929 HG2    QSI 39 
QSI HN21   1HN2   H 0 0 N N N 42.202 36.018 14.897 3.892  0.878  -8.503 HN21   QSI 40 
QSI HN22   2HN2   H 0 0 N N N 40.626 35.642 14.165 4.515  1.401  -7.034 HN22   QSI 41 
QSI HN0    HN0    H 0 1 N N N 46.644 29.883 14.388 -1.240 1.282  -3.178 HN0    QSI 42 
QSI "H5'1" "1H5'" H 0 0 N N N 43.638 29.153 13.370 -2.189 1.089  -0.329 "H5'1" QSI 43 
QSI "H5'2" "2H5'" H 0 0 N N N 43.339 27.542 12.970 -3.880 0.535  -0.288 "H5'2" QSI 44 
QSI "H4'"  "H4'"  H 0 1 N N N 41.312 28.898 13.183 -3.299 -1.074 1.520  "H4'"  QSI 45 
QSI "H1'"  "H1'"  H 0 1 N N N 39.068 27.074 14.991 -1.369 -0.951 3.603  "H1'"  QSI 46 
QSI H2     H2     H 0 1 N N N 36.122 25.684 18.114 1.483  -1.031 7.411  H2     QSI 47 
QSI HN61   1HN6   H 0 0 N N N 40.480 23.911 20.518 5.455  0.035  5.441  HN61   QSI 48 
QSI HN62   2HN6   H 0 0 N N N 39.045 23.086 20.373 5.098  0.400  3.841  HN62   QSI 49 
QSI H8     H8     H 0 1 N N N 42.417 26.439 16.842 1.117  0.551  1.106  H8     QSI 50 
QSI "H2'"  "H2'"  H 0 1 N N N 39.652 29.220 16.668 -1.110 1.966  2.679  "H2'"  QSI 51 
QSI HO2    HO2    H 0 1 N N N 38.990 30.425 14.903 -2.444 2.242  4.519  HO2    QSI 52 
QSI "H3'"  "H3'"  H 0 1 N N N 42.130 29.219 16.146 -3.255 1.836  1.719  "H3'"  QSI 53 
QSI HO3    HO3    H 0 1 N N N 41.237 31.260 15.709 -4.208 1.304  3.759  HO3    QSI 54 
# 
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 
QSI N     CA     SING N N 1  
QSI N     HN1    SING N N 2  
QSI N     HN2    SING N N 3  
QSI CA    CB     SING N N 4  
QSI CA    C      SING N N 5  
QSI CA    HA     SING N N 6  
QSI CB    CG     SING N N 7  
QSI CB    HB1    SING N N 8  
QSI CB    HB2    SING N N 9  
QSI CG    CD     SING N N 10 
QSI CG    HG1    SING N N 11 
QSI CG    HG2    SING N N 12 
QSI CD    OE1    DOUB N N 13 
QSI CD    NE2    SING N N 14 
QSI NE2   HN21   SING N N 15 
QSI NE2   HN22   SING N N 16 
QSI C     O      DOUB N N 17 
QSI C     N10    SING N N 18 
QSI N10   S      SING N N 19 
QSI N10   HN0    SING N N 20 
QSI S     O1S    DOUB N N 21 
QSI S     O2S    DOUB N N 22 
QSI S     "O5'"  SING N N 23 
QSI "O5'" "C5'"  SING N N 24 
QSI "C5'" "C4'"  SING N N 25 
QSI "C5'" "H5'1" SING N N 26 
QSI "C5'" "H5'2" SING N N 27 
QSI "C4'" "O4'"  SING N N 28 
QSI "C4'" "C3'"  SING N N 29 
QSI "C4'" "H4'"  SING N N 30 
QSI "O4'" "C1'"  SING N N 31 
QSI "C1'" N9     SING N N 32 
QSI "C1'" "C2'"  SING N N 33 
QSI "C1'" "H1'"  SING N N 34 
QSI N9    C4     SING Y N 35 
QSI N9    C8     SING Y N 36 
QSI C4    N3     SING Y N 37 
QSI C4    C5     DOUB Y N 38 
QSI N3    C2     DOUB Y N 39 
QSI C2    N1     SING Y N 40 
QSI C2    H2     SING N N 41 
QSI N1    C6     DOUB Y N 42 
QSI C6    N6     SING N N 43 
QSI C6    C5     SING Y N 44 
QSI N6    HN61   SING N N 45 
QSI N6    HN62   SING N N 46 
QSI C5    N7     SING Y N 47 
QSI N7    C8     DOUB Y N 48 
QSI C8    H8     SING N N 49 
QSI "C2'" "O2'"  SING N N 50 
QSI "C2'" "C3'"  SING N N 51 
QSI "C2'" "H2'"  SING N N 52 
QSI "O2'" HO2    SING N N 53 
QSI "C3'" "O3'"  SING N N 54 
QSI "C3'" "H3'"  SING N N 55 
QSI "O3'" HO3    SING N N 56 
# 
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 
QSI SMILES           ACDLabs              10.04 O=C(N)CCC(N)C(=O)NS(=O)(=O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O 
QSI InChI            InChI                1.02b 
InChI=1/C15H22N8O8S/c16-6(1-2-8(17)24)14(27)22-32(28,29)30-3-7-10(25)11(26)15(31-7)23-5-21-9-12(18)19-4-20-13(9)23/h4-7,10-11,15,25-26H,1-3,16H2,(H2,17,24)(H,22,27)(H2,18,19,20)/t6-,7+,10+,11+,15+/m0/s1/f/h22H,17-18H2 
QSI InChIKey         InChI                1.02b KXWKSWRGZLZHEF-JQFNNUNHDD 
QSI SMILES_CANONICAL CACTVS               3.341 N[C@@H](CCC(N)=O)C(=O)N[S](=O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23 
QSI SMILES           CACTVS               3.341 N[CH](CCC(N)=O)C(=O)N[S](=O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23 
QSI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COS(=O)(=O)NC(=O)[C@H](CCC(=O)N)N)O)O)N 
QSI SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COS(=O)(=O)NC(=O)C(CCC(=O)N)N)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 
QSI "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-(L-glutaminylsulfamoyl)adenosine"                                                                               
QSI "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)-2,5-diamino-5-oxo-pentanoyl]sulfamate" 
# 
