data_GUB # _chem_comp.id GUB _chem_comp.name "9-alpha-L-lyxofuranosyl-N-(2-phenylethyl)-9H-purin-6-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H21 N5 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-04-10 _chem_comp.pdbx_modified_date 2011-06-04 _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 371.390 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GUB _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 3GUB _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 GUB C2 C2 C 0 1 N N N -24.777 5.626 -6.550 4.716 1.215 0.360 C2 GUB 1 GUB C3 C3 C 0 1 N N N -24.263 5.714 -7.984 3.750 0.090 -0.017 C3 GUB 2 GUB C5 C5 C 0 1 Y N N -25.680 5.541 -10.036 1.318 -0.262 -0.242 C5 GUB 3 GUB O18 O18 O 0 1 N N N -21.049 1.049 -12.580 -6.093 2.982 -0.415 O18 GUB 4 GUB C17 C17 C 0 1 N N N -21.575 0.427 -13.768 -6.367 1.699 0.149 C17 GUB 5 GUB C16 C16 C 0 1 N N S -22.595 1.518 -13.833 -5.052 0.954 0.389 C16 GUB 6 GUB C19 C19 C 0 1 N N S -22.414 2.804 -14.660 -5.310 -0.390 1.116 C19 GUB 7 GUB O20 O20 O 0 1 N N N -21.614 2.751 -15.859 -6.517 -0.998 0.651 O20 GUB 8 GUB O15 O15 O 0 1 N N N -23.962 1.229 -13.585 -4.461 0.550 -0.865 O15 GUB 9 GUB C14 C14 C 0 1 N N R -24.598 2.489 -13.663 -3.562 -0.533 -0.576 C14 GUB 10 GUB C21 C21 C 0 1 N N R -23.862 3.255 -14.780 -4.075 -1.225 0.701 C21 GUB 11 GUB O22 O22 O 0 1 N N N -24.374 2.831 -16.043 -4.454 -2.574 0.420 O22 GUB 12 GUB N13 N13 N 0 1 Y N N -24.460 3.179 -12.335 -2.211 -0.012 -0.352 N13 GUB 13 GUB C12 C12 C 0 1 Y N N -23.508 3.032 -11.384 -1.889 1.254 0.041 C12 GUB 14 GUB N11 N11 N 0 1 Y N N -23.759 3.885 -10.363 -0.597 1.372 0.144 N11 GUB 15 GUB C10 C10 C 0 1 Y N N -24.899 4.563 -10.665 -0.009 0.194 -0.175 C10 GUB 16 GUB C9 C9 C 0 1 Y N N -25.319 4.102 -11.913 -1.038 -0.708 -0.497 C9 GUB 17 GUB N6 N6 N 0 1 Y N N -26.777 6.013 -10.692 1.538 -1.521 -0.605 N6 GUB 18 GUB C7 C7 C 0 1 Y N N -27.159 5.534 -11.893 0.538 -2.333 -0.897 C7 GUB 19 GUB N8 N8 N 0 1 Y N N -26.428 4.593 -12.514 -0.721 -1.949 -0.849 N8 GUB 20 GUB N4 N4 N 0 1 N N N -25.392 6.108 -8.830 2.373 0.583 0.058 N4 GUB 21 GUB C1 C1 C 0 1 Y N N -23.727 5.102 -5.581 6.133 0.707 0.283 C1 GUB 22 GUB C23 C23 C 0 1 Y N N -23.465 3.737 -5.510 6.840 0.810 -0.900 C23 GUB 23 GUB C24 C24 C 0 1 Y N N -22.507 3.261 -4.610 8.140 0.344 -0.970 C24 GUB 24 GUB C25 C25 C 0 1 Y N N -21.821 4.159 -3.774 8.733 -0.223 0.142 C25 GUB 25 GUB C26 C26 C 0 1 Y N N -22.091 5.519 -3.855 8.025 -0.325 1.326 C26 GUB 26 GUB C27 C27 C 0 1 Y N N -23.057 5.991 -4.739 6.727 0.144 1.398 C27 GUB 27 GUB H2 H2 H 0 1 N N N -25.077 6.634 -6.226 4.590 2.048 -0.331 H2 GUB 28 GUB H2A H2A H 0 1 N N N -25.622 4.921 -6.541 4.505 1.550 1.376 H2A GUB 29 GUB H3 H3 H 0 1 N N N -23.458 6.461 -8.053 3.961 -0.245 -1.032 H3 GUB 30 GUB H3A H3A H 0 1 N N N -23.854 4.746 -8.309 3.876 -0.744 0.674 H3A GUB 31 GUB HO18 HO18 H 0 0 N N N -20.933 0.393 -11.903 -6.882 3.510 -0.594 HO18 GUB 32 GUB H17 H17 H 0 1 N N N -20.894 0.322 -14.626 -6.892 1.823 1.097 H17 GUB 33 GUB H17A H17A H 0 0 N N N -21.875 -0.631 -13.770 -6.990 1.125 -0.537 H17A GUB 34 GUB H16 H16 H 0 1 N N N -22.111 1.809 -12.889 -4.361 1.573 0.960 H16 GUB 35 GUB H19 H19 H 0 1 N N N -21.754 3.542 -14.182 -5.340 -0.248 2.196 H19 GUB 36 GUB HO20 HO20 H 0 0 N N N -22.183 2.739 -16.620 -7.310 -0.468 0.808 HO20 GUB 37 GUB H14 H14 H 0 1 N N N -25.672 2.421 -13.889 -3.555 -1.240 -1.405 H14 GUB 38 GUB H21 H21 H 0 1 N N N -23.978 4.346 -14.699 -3.315 -1.197 1.482 H21 GUB 39 GUB HO22 HO22 H 0 0 N N N -25.318 2.737 -15.987 -4.839 -3.040 1.175 HO22 GUB 40 GUB H12 H12 H 0 1 N N N -22.678 2.342 -11.432 -2.601 2.042 0.237 H12 GUB 41 GUB H7 H7 H 0 1 N N N -28.058 5.909 -12.359 0.761 -3.349 -1.188 H7 GUB 42 GUB HN4 HN4 H 0 1 N N N -26.203 5.942 -8.269 2.200 1.501 0.317 HN4 GUB 43 GUB H23 H23 H 0 1 N N N -24.000 3.048 -6.148 6.378 1.253 -1.769 H23 GUB 44 GUB H24 H24 H 0 1 N N N -22.294 2.204 -4.557 8.693 0.424 -1.895 H24 GUB 45 GUB H25 H25 H 0 1 N N N -21.087 3.793 -3.072 9.748 -0.588 0.087 H25 GUB 46 GUB H26 H26 H 0 1 N N N -21.549 6.213 -3.230 8.488 -0.769 2.195 H26 GUB 47 GUB H27 H27 H 0 1 N N N -23.288 7.045 -4.773 6.176 0.068 2.323 H27 GUB 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 GUB C2 C3 SING N N 1 GUB C2 C1 SING N N 2 GUB C3 N4 SING N N 3 GUB C5 C10 DOUB Y N 4 GUB C5 N6 SING Y N 5 GUB C5 N4 SING N N 6 GUB O18 C17 SING N N 7 GUB C17 C16 SING N N 8 GUB C16 C19 SING N N 9 GUB C16 O15 SING N N 10 GUB C19 O20 SING N N 11 GUB C19 C21 SING N N 12 GUB O15 C14 SING N N 13 GUB C14 C21 SING N N 14 GUB C14 N13 SING N N 15 GUB C21 O22 SING N N 16 GUB N13 C12 SING Y N 17 GUB N13 C9 SING Y N 18 GUB C12 N11 DOUB Y N 19 GUB N11 C10 SING Y N 20 GUB C10 C9 SING Y N 21 GUB C9 N8 DOUB Y N 22 GUB N6 C7 DOUB Y N 23 GUB C7 N8 SING Y N 24 GUB C1 C23 DOUB Y N 25 GUB C1 C27 SING Y N 26 GUB C23 C24 SING Y N 27 GUB C24 C25 DOUB Y N 28 GUB C25 C26 SING Y N 29 GUB C26 C27 DOUB Y N 30 GUB C2 H2 SING N N 31 GUB C2 H2A SING N N 32 GUB C3 H3 SING N N 33 GUB C3 H3A SING N N 34 GUB O18 HO18 SING N N 35 GUB C17 H17 SING N N 36 GUB C17 H17A SING N N 37 GUB C16 H16 SING N N 38 GUB C19 H19 SING N N 39 GUB O20 HO20 SING N N 40 GUB C14 H14 SING N N 41 GUB C21 H21 SING N N 42 GUB O22 HO22 SING N N 43 GUB C12 H12 SING N N 44 GUB C7 H7 SING N N 45 GUB N4 HN4 SING N N 46 GUB C23 H23 SING N N 47 GUB C24 H24 SING N N 48 GUB C25 H25 SING N N 49 GUB C26 H26 SING N N 50 GUB C27 H27 SING N N 51 # 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 GUB SMILES ACDLabs 10.04 "n2c1c(ncnc1n(c2)C3OC(C(O)C3O)CO)NCCc4ccccc4" GUB SMILES_CANONICAL CACTVS 3.341 "OC[C@@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCCc4ccccc4)ncnc23" GUB SMILES CACTVS 3.341 "OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(NCCc4ccccc4)ncnc23" GUB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNc2c3c(ncn2)n(cn3)[C@H]4[C@@H]([C@@H]([C@@H](O4)CO)O)O" GUB SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNc2c3c(ncn2)n(cn3)C4C(C(C(O4)CO)O)O" GUB InChI InChI 1.03 "InChI=1S/C18H21N5O4/c24-8-12-14(25)15(26)18(27-12)23-10-22-13-16(20-9-21-17(13)23)19-7-6-11-4-2-1-3-5-11/h1-5,9-10,12,14-15,18,24-26H,6-8H2,(H,19,20,21)/t12-,14+,15+,18+/m0/s1" GUB InChIKey InChI 1.03 LGZYEDZSPHLISU-KDQZPGIASA-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 GUB "SYSTEMATIC NAME" ACDLabs 10.04 "9-alpha-L-lyxofuranosyl-N-(2-phenylethyl)-9H-purin-6-amine" GUB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(phenethylamino)purin-9-yl]oxolane-3,4-diol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site GUB "Create component" 2009-04-10 RCSB GUB "Modify aromatic_flag" 2011-06-04 RCSB GUB "Modify descriptor" 2011-06-04 RCSB #