data_BIG
# 
_chem_comp.id                                    BIG 
_chem_comp.name                                  (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H25 N5 O S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "butylthio-DADMe-Immucillin A" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-07-10 
_chem_comp.pdbx_modified_date                    2009-03-06 
_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                        335.468 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BIG 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3DP9 
_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 
BIG C2     C2     C 0 1 Y N N -1.321 -4.128 5.295 4.595   -2.135 1.293  C2     BIG 1  
BIG C5     C5     C 0 1 Y N N -3.934 -3.464 4.593 4.847   -0.123 -0.471 C5     BIG 2  
BIG C4     C4     C 0 1 Y N N -3.235 -2.914 5.756 3.603   -0.736 -0.240 C4     BIG 3  
BIG C8     C8     C 0 1 Y N N -5.326 -2.046 5.613 3.338   0.887  -1.785 C8     BIG 4  
BIG "O3'"  "O3'"  O 0 1 N N N -1.263 2.082  8.214 -0.350  2.625  1.856  "O3'"  BIG 5  
BIG "C3'"  "C3'"  C 0 1 N N R -1.219 1.114  7.158 -0.825  2.181  0.584  "C3'"  BIG 6  
BIG "C4'"  "C4'"  C 0 1 N N S -2.117 1.510  5.992 -1.686  0.912  0.747  "C4'"  BIG 7  
BIG "C5'"  "C5'"  C 0 1 N N N -1.644 0.896  4.676 -3.087  1.143  0.177  "C5'"  BIG 8  
BIG "S5'"  "S5'"  S 0 1 N N N -0.393 1.862  3.883 -4.123  -0.308 0.512  "S5'"  BIG 9  
BIG C20    C20    C 0 1 N N N -1.338 3.108  3.054 -5.716  0.149  -0.226 C20    BIG 10 
BIG C21    C21    C 0 1 N N N -0.402 4.151  2.453 -6.717  -0.990 -0.025 C21    BIG 11 
BIG C22    C22    C 0 1 N N N -1.135 5.457  2.161 -8.061  -0.605 -0.648 C22    BIG 12 
BIG C23    C23    C 0 1 N N N -0.977 5.826  0.704 -9.061  -1.744 -0.446 C23    BIG 13 
BIG "C1'"  "C1'"  C 0 1 N N N -3.459 0.879  6.322 -0.951  -0.178 -0.063 "C1'"  BIG 14 
BIG "N1'"  "N1'"  N 0 1 N N N -3.255 0.114  7.571 0.460   0.283  -0.116 "N1'"  BIG 15 
BIG "C2'"  "C2'"  C 0 1 N N N -1.825 -0.155 7.709 0.357   1.752  -0.311 "C2'"  BIG 16 
BIG C10    C10    C 0 1 N N N -3.975 -1.176 7.647 1.178   -0.347 -1.232 C10    BIG 17 
BIG N7     N7     N 0 1 Y N N -5.158 -2.903 4.555 4.651   0.858  -1.416 N7     BIG 18 
BIG C6     C6     C 0 1 Y N N -3.159 -4.431 3.790 5.955   -0.589 0.245  C6     BIG 19 
BIG N6     N6     N 0 1 N N N -3.684 -5.023 2.689 7.206   -0.022 0.060  N6     BIG 20 
BIG N3     N3     N 0 1 Y N N -1.962 -3.258 6.082 3.524   -1.733 0.646  N3     BIG 21 
BIG C9     C9     C 0 1 Y N N -4.176 -1.981 6.396 2.651   -0.054 -1.111 C9     BIG 22 
BIG N1     N1     N 0 1 Y N N -1.892 -4.695 4.204 5.782   -1.586 1.107  N1     BIG 23 
BIG H2     H2     H 0 1 N N N -0.302 -4.391 5.539 4.500   -2.940 2.007  H2     BIG 24 
BIG H8     H8     H 0 1 N N N -6.232 -1.494 5.813 2.913   1.564  -2.512 H8     BIG 25 
BIG "HO3'" "HO3'" H 0 0 N N N -1.273 1.636  9.053 0.198   3.421  1.815  "HO3'" BIG 26 
BIG "H3'"  "H3'"  H 0 1 N N N -0.178 1.017  6.815 -1.401  2.970  0.099  "H3'"  BIG 27 
BIG "H4'"  "H4'"  H 0 1 N N N -2.133 2.603  5.870 -1.747  0.628  1.797  "H4'"  BIG 28 
BIG "H5'"  "H5'"  H 0 1 N N N -1.231 -0.102 4.887 -3.530  2.022  0.646  "H5'"  BIG 29 
BIG "H5'A" "H5'A" H 0 0 N N N -2.510 0.850  3.999 -3.020  1.301  -0.900 "H5'A" BIG 30 
BIG H20    H20    H 0 1 N N N -1.930 2.643  2.252 -6.093  1.053  0.253  H20    BIG 31 
BIG H20A   H20A   H 0 0 N N N -2.010 3.595  3.776 -5.583  0.332  -1.293 H20A   BIG 32 
BIG H21    H21    H 0 1 N N N 0.410  4.352  3.167 -6.340  -1.894 -0.504 H21    BIG 33 
BIG H21A   H21A   H 0 0 N N N -0.006 3.756  1.506 -6.850  -1.173 1.041  H21A   BIG 34 
BIG H22    H22    H 0 1 N N N -2.204 5.333  2.390 -8.437  0.299  -0.168 H22    BIG 35 
BIG H22A   H22A   H 0 0 N N N -0.708 6.257  2.784 -7.928  -0.422 -1.714 H22A   BIG 36 
BIG H23    H23    H 0 1 N N N -0.939 6.921  0.605 -10.019 -1.470 -0.890 H23    BIG 37 
BIG H23A   H23A   H 0 0 N N N -0.045 5.390  0.314 -8.685  -2.648 -0.926 H23A   BIG 38 
BIG H23B   H23B   H 0 0 N N N -1.832 5.436  0.132 -9.194  -1.927 0.620  H23B   BIG 39 
BIG "H1'"  "H1'"  H 0 1 N N N -4.227 1.654  6.463 -1.018  -1.140 0.445  "H1'"  BIG 40 
BIG "H1'A" "H1'A" H 0 0 N N N -3.808 0.229  5.506 -1.366  -0.249 -1.069 "H1'A" BIG 41 
BIG "H2'"  "H2'"  H 0 1 N N N -1.514 -1.044 7.141 0.148   1.983  -1.355 "H2'"  BIG 42 
BIG "H2'A" "H2'A" H 0 0 N N N -1.514 -0.383 8.739 1.276   2.243  0.011  "H2'A" BIG 43 
BIG H10    H10    H 0 1 N N N -3.398 -1.812 8.334 1.019   -1.425 -1.204 H10    BIG 44 
BIG H10A   H10A   H 0 0 N N N -4.995 -0.894 7.949 0.805   0.051  -2.175 H10A   BIG 45 
BIG HN7    HN7    H 0 1 N N N -5.847 -3.086 3.854 5.342   1.442  -1.765 HN7    BIG 46 
BIG HN6    HN6    H 0 1 N N N -3.813 -4.339 1.972 7.321   0.705  -0.572 HN6    BIG 47 
BIG HN6A   HN6A   H 0 0 N N N -3.060 -5.733 2.363 7.968   -0.354 0.561  HN6A   BIG 48 
# 
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 
BIG C2    N3     DOUB Y N 1  
BIG C2    N1     SING Y N 2  
BIG C5    C4     DOUB N N 3  
BIG C5    N7     SING Y N 4  
BIG C5    C6     SING Y N 5  
BIG C4    N3     SING Y N 6  
BIG C4    C9     SING Y N 7  
BIG C8    N7     SING Y N 8  
BIG C8    C9     DOUB Y N 9  
BIG "O3'" "C3'"  SING Y N 10 
BIG "C3'" "C4'"  SING N N 11 
BIG "C3'" "C2'"  SING N N 12 
BIG "C4'" "C5'"  SING N N 13 
BIG "C4'" "C1'"  SING N N 14 
BIG "C5'" "S5'"  SING N N 15 
BIG "S5'" C20    SING N N 16 
BIG C20   C21    SING N N 17 
BIG C21   C22    SING N N 18 
BIG C22   C23    SING N N 19 
BIG "C1'" "N1'"  SING N N 20 
BIG "N1'" "C2'"  SING N N 21 
BIG "N1'" C10    SING N N 22 
BIG C10   C9     SING N N 23 
BIG C6    N6     SING N N 24 
BIG C6    N1     DOUB N N 25 
BIG C2    H2     SING N N 26 
BIG C8    H8     SING N N 27 
BIG "O3'" "HO3'" SING N N 28 
BIG "C3'" "H3'"  SING N N 29 
BIG "C4'" "H4'"  SING N N 30 
BIG "C5'" "H5'"  SING N N 31 
BIG "C5'" "H5'A" SING N N 32 
BIG C20   H20    SING N N 33 
BIG C20   H20A   SING N N 34 
BIG C21   H21    SING N N 35 
BIG C21   H21A   SING N N 36 
BIG C22   H22    SING N N 37 
BIG C22   H22A   SING N N 38 
BIG C23   H23    SING N N 39 
BIG C23   H23A   SING N N 40 
BIG C23   H23B   SING N N 41 
BIG "C1'" "H1'"  SING N N 42 
BIG "C1'" "H1'A" SING N N 43 
BIG "C2'" "H2'"  SING N N 44 
BIG "C2'" "H2'A" SING N N 45 
BIG C10   H10    SING N N 46 
BIG C10   H10A   SING N N 47 
BIG N7    HN7    SING Y N 48 
BIG N6    HN6    SING N N 49 
BIG N6    HN6A   SING N N 50 
# 
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 
BIG SMILES           ACDLabs              10.04 S(CCCC)CC3CN(Cc2cnc1c2ncnc1N)CC3O                                                                                                                              
BIG InChI            InChI                1.02b InChI=1/C16H25N5OS/c1-2-3-4-23-9-12-7-21(8-13(12)22)6-11-5-18-15-14(11)19-10-20-16(15)17/h5,10,12-13,18,22H,2-4,6-9H2,1H3,(H2,17,19,20)/t12-,13+/m1/s1/f/h17H2 
BIG InChIKey         InChI                1.02b LTSUEVPGSXUJHT-SBZHIHSKDU                                                                                                                                      
BIG SMILES_CANONICAL CACTVS               3.341 CCCCSC[C@H]1CN(C[C@@H]1O)Cc2c[nH]c3c(N)ncnc23                                                                                                                  
BIG SMILES           CACTVS               3.341 CCCCSC[CH]1CN(C[CH]1O)Cc2c[nH]c3c(N)ncnc23                                                                                                                     
BIG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCSC[C@H]1C[N@](C[C@@H]1O)Cc2c[nH]c3c2ncnc3N                                                                                                                 
BIG SMILES           "OpenEye OEToolkits" 1.5.0 CCCCSCC1CN(CC1O)Cc2c[nH]c3c2ncnc3N                                                                                                                             
# 
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 
BIG "SYSTEMATIC NAME" ACDLabs              10.04 (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol  
BIG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,3R,4S)-1-[(4-amino-5H-pyrrolo[5,4-e]pyrimidin-7-yl)methyl]-4-(butylsulfanylmethyl)pyrrolidin-3-ol 
# 
