data_CAW # _chem_comp.id CAW _chem_comp.name "N-[[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]carbamoyl]naphthalene-1-carboxamide" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H20 N2 O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-11-21 _chem_comp.pdbx_modified_date 2014-09-05 _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 376.361 _chem_comp.one_letter_code ? _chem_comp.three_letter_code CAW _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 3ZCS _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 CAW C9 C9 C 0 1 Y N N 35.345 25.707 34.272 -3.540 -1.271 -1.505 C9 CAW 1 CAW C14 C14 C 0 1 Y N N 36.331 26.169 35.144 -4.776 -1.662 -2.004 C14 CAW 2 CAW C13 C13 C 0 1 Y N N 37.412 26.885 34.625 -5.942 -1.189 -1.485 C13 CAW 3 CAW C12 C12 C 0 1 Y N N 37.484 27.133 33.251 -5.933 -0.278 -0.414 C12 CAW 4 CAW C18 C18 C 0 1 Y N N 38.561 27.855 32.751 -7.128 0.219 0.132 C18 CAW 5 CAW C17 C17 C 0 1 Y N N 38.648 28.113 31.387 -7.079 1.100 1.170 C17 CAW 6 CAW C16 C16 C 0 1 Y N N 37.668 27.647 30.514 -5.860 1.517 1.699 C16 CAW 7 CAW C15 C15 C 0 1 Y N N 36.590 26.930 31.014 -4.682 1.055 1.193 C15 CAW 8 CAW C11 C11 C 0 1 Y N N 36.486 26.665 32.378 -4.695 0.148 0.127 C11 CAW 9 CAW C10 C10 C 0 1 Y N N 35.404 25.939 32.891 -3.457 -0.374 -0.447 C10 CAW 10 CAW C8 C8 C 0 1 N N N 34.350 25.443 32.092 -2.147 0.042 0.085 C8 CAW 11 CAW O8 O8 O 0 1 N N N 33.190 25.640 32.476 -2.084 0.905 0.938 O8 CAW 12 CAW N2 N2 N 0 1 N N N 34.711 24.765 30.949 -1.019 -0.535 -0.375 N2 CAW 13 CAW C7 C7 C 0 1 N N N 33.789 24.208 30.107 0.179 -0.154 0.111 C7 CAW 14 CAW O7 O7 O 0 1 N N N 32.578 24.273 30.326 0.242 0.709 0.965 O7 CAW 15 CAW N1 N1 N 0 1 N N N 34.242 23.579 28.994 1.307 -0.731 -0.349 N1 CAW 16 CAW C1 C1 C 0 1 N N R 33.332 22.942 28.016 2.609 -0.317 0.180 C1 CAW 17 CAW O5 O5 O 0 1 N N N 33.301 21.507 28.247 3.176 0.679 -0.674 O5 CAW 18 CAW C5 C5 C 0 1 N N R 32.210 20.899 27.521 4.442 1.173 -0.234 C5 CAW 19 CAW C6 C6 C 0 1 N N N 32.154 19.417 27.934 4.936 2.248 -1.204 C6 CAW 20 CAW O6 O6 O 0 1 N N N 33.269 18.702 27.384 4.055 3.372 -1.159 O6 CAW 21 CAW C4 C4 C 0 1 N N S 32.435 21.045 25.987 5.451 0.022 -0.191 C4 CAW 22 CAW O4 O4 O 0 1 N N N 31.265 20.574 25.275 6.702 0.502 0.305 O4 CAW 23 CAW C3 C3 C 0 1 N N S 32.691 22.529 25.607 4.921 -1.076 0.737 C3 CAW 24 CAW O3 O3 O 0 1 N N N 33.123 22.580 24.239 5.821 -2.186 0.726 O3 CAW 25 CAW C2 C2 C 0 1 N N R 33.773 23.159 26.545 3.544 -1.528 0.240 C2 CAW 26 CAW O2 O2 O 0 1 N N N 33.932 24.559 26.253 3.008 -2.501 1.138 O2 CAW 27 CAW H9 H9 H 0 1 N N N 34.510 25.153 34.674 -2.636 -1.671 -1.940 H9 CAW 28 CAW H14 H14 H 0 1 N N N 36.260 25.976 36.204 -4.813 -2.360 -2.827 H14 CAW 29 CAW H13 H13 H 0 1 N N N 38.189 27.246 35.282 -6.883 -1.516 -1.900 H13 CAW 30 CAW H18 H18 H 0 1 N N N 39.329 28.215 33.420 -8.081 -0.095 -0.269 H18 CAW 31 CAW H17 H17 H 0 1 N N N 39.483 28.680 31.002 -7.999 1.481 1.588 H17 CAW 32 CAW H16 H16 H 0 1 N N N 37.746 27.842 29.455 -5.849 2.216 2.523 H16 CAW 33 CAW H15 H15 H 0 1 N N N 35.825 26.574 30.340 -3.744 1.386 1.613 H15 CAW 34 CAW H2 H2 H 0 1 N N N 35.682 24.677 30.727 -1.069 -1.224 -1.057 H2 CAW 35 CAW H1 H1 H 0 1 N N N 35.228 23.544 28.828 1.257 -1.419 -1.030 H1 CAW 36 CAW HA HA H 0 1 N N N 32.321 23.357 28.138 2.481 0.093 1.181 HA CAW 37 CAW HB HB H 0 1 N N N 34.723 22.630 26.383 3.640 -1.963 -0.755 HB CAW 38 CAW H5 H5 H 0 1 N N N 31.258 21.382 27.787 4.338 1.603 0.762 H5 CAW 39 CAW H61C H61C H 0 0 N N N 32.183 19.345 29.031 5.940 2.561 -0.919 H61C CAW 40 CAW H62C H62C H 0 0 N N N 31.219 18.972 27.562 4.956 1.842 -2.216 H62C CAW 41 CAW H4 H4 H 0 1 N N N 33.316 20.451 25.702 5.587 -0.382 -1.194 H4 CAW 42 CAW H6 H6 H 0 1 N N N 33.222 17.790 27.647 4.308 4.094 -1.751 H6 CAW 43 CAW HC HC H 0 1 N N N 31.405 20.664 24.340 7.390 -0.176 0.359 HC CAW 44 CAW H3 H3 H 0 1 N N N 31.753 23.090 25.731 4.834 -0.687 1.751 H3 CAW 45 CAW HD HD H 0 1 N N N 33.284 23.483 23.991 5.546 -2.920 1.293 HD CAW 46 CAW H2A H2A H 0 1 N N N 34.202 24.666 25.348 2.133 -2.829 0.887 H2A CAW 47 # 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 CAW C9 C14 SING Y N 1 CAW C9 C10 DOUB Y N 2 CAW C14 C13 DOUB Y N 3 CAW C13 C12 SING Y N 4 CAW C12 C18 SING Y N 5 CAW C12 C11 DOUB Y N 6 CAW C18 C17 DOUB Y N 7 CAW C17 C16 SING Y N 8 CAW C16 C15 DOUB Y N 9 CAW C15 C11 SING Y N 10 CAW C11 C10 SING Y N 11 CAW C10 C8 SING N N 12 CAW C8 O8 DOUB N N 13 CAW C8 N2 SING N N 14 CAW N2 C7 SING N N 15 CAW C7 O7 DOUB N N 16 CAW C7 N1 SING N N 17 CAW N1 C1 SING N N 18 CAW C1 O5 SING N N 19 CAW C1 C2 SING N N 20 CAW O5 C5 SING N N 21 CAW C5 C6 SING N N 22 CAW C5 C4 SING N N 23 CAW C6 O6 SING N N 24 CAW C4 O4 SING N N 25 CAW C4 C3 SING N N 26 CAW C3 O3 SING N N 27 CAW C3 C2 SING N N 28 CAW O2 C2 SING N N 29 CAW C9 H9 SING N N 30 CAW C14 H14 SING N N 31 CAW C13 H13 SING N N 32 CAW C18 H18 SING N N 33 CAW C17 H17 SING N N 34 CAW C16 H16 SING N N 35 CAW C15 H15 SING N N 36 CAW N2 H2 SING N N 37 CAW N1 H1 SING N N 38 CAW C1 HA SING N N 39 CAW C2 HB SING N N 40 CAW C5 H5 SING N N 41 CAW C6 H61C SING N N 42 CAW C6 H62C SING N N 43 CAW C4 H4 SING N N 44 CAW O6 H6 SING N N 45 CAW O4 HC SING N N 46 CAW C3 H3 SING N N 47 CAW O3 HD SING N N 48 CAW O2 H2A SING N N 49 # 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 CAW SMILES ACDLabs 12.01 "O=C(NC1OC(C(O)C(O)C1O)CO)NC(=O)c3c2ccccc2ccc3" CAW InChI InChI 1.03 "InChI=1S/C18H20N2O7/c21-8-12-13(22)14(23)15(24)17(27-12)20-18(26)19-16(25)11-7-3-5-9-4-1-2-6-10(9)11/h1-7,12-15,17,21-24H,8H2,(H2,19,20,25,26)/t12-,13-,14+,15-,17-/m1/s1" CAW InChIKey InChI 1.03 VEHFJUDJKOIMSO-OWVAZHOYSA-N CAW SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@@H](NC(=O)NC(=O)c2cccc3ccccc23)[C@H](O)[C@@H](O)[C@@H]1O" CAW SMILES CACTVS 3.385 "OC[CH]1O[CH](NC(=O)NC(=O)c2cccc3ccccc23)[CH](O)[CH](O)[CH]1O" CAW SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)cccc2C(=O)NC(=O)N[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O" CAW SMILES "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)cccc2C(=O)NC(=O)NC3C(C(C(C(O3)CO)O)O)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 CAW "SYSTEMATIC NAME" ACDLabs 12.01 "N-[(naphthalen-1-ylcarbonyl)carbamoyl]-beta-D-glucopyranosylamine" CAW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-[[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]carbamoyl]naphthalene-1-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site CAW "Create component" 2012-11-21 EBI CAW "Initial release" 2013-12-11 RCSB CAW "Modify descriptor" 2014-09-05 RCSB #