data_VMP # _chem_comp.id VMP _chem_comp.name "N-[[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]carbamoyl]naphthalene-2-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 VMP _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 3ZCT _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 VMP C10 C10 C 0 1 Y N N 36.485 26.444 32.266 -4.342 -0.583 -0.787 C10 VMP 1 VMP C11 C11 C 0 1 Y N N 37.563 26.934 33.009 -5.647 -0.332 -0.337 C11 VMP 2 VMP C24 C24 C 0 1 Y N N 38.618 27.578 32.357 -6.761 -0.886 -0.993 C24 VMP 3 VMP C26 C26 C 0 1 Y N N 39.694 28.070 33.100 -8.014 -0.623 -0.530 C26 VMP 4 VMP C27 C27 C 0 1 Y N N 39.713 27.920 34.490 -8.211 0.189 0.585 C27 VMP 5 VMP C25 C25 C 0 1 Y N N 38.663 27.280 35.148 -7.156 0.742 1.245 C25 VMP 6 VMP C12 C12 C 0 1 Y N N 37.584 26.787 34.405 -5.848 0.494 0.798 C12 VMP 7 VMP C13 C13 C 0 1 Y N N 36.525 26.151 35.062 -4.737 1.052 1.459 C13 VMP 8 VMP C14 C14 C 0 1 Y N N 35.453 25.663 34.316 -3.482 0.799 1.009 C14 VMP 9 VMP C9 C9 C 0 1 Y N N 35.431 25.801 32.926 -3.270 -0.019 -0.115 C9 VMP 10 VMP C8 C8 C 0 1 N N N 34.231 25.253 32.138 -1.893 -0.279 -0.583 C8 VMP 11 VMP O8 O8 O 0 1 N N N 33.096 25.381 32.599 -1.705 -0.984 -1.555 O8 VMP 12 VMP N2 N2 N 0 1 N N N 34.531 24.664 30.966 -0.846 0.266 0.067 N2 VMP 13 VMP C7 C7 C 0 1 N N N 33.626 24.112 30.134 0.410 0.029 -0.360 C7 VMP 14 VMP O7 O7 O 0 1 N N N 32.413 24.120 30.365 0.598 -0.676 -1.332 O7 VMP 15 VMP N1 N1 N 0 1 N N N 34.115 23.563 29.015 1.457 0.575 0.290 N1 VMP 16 VMP C1 C1 C 0 1 N N R 33.211 22.927 28.020 2.822 0.317 -0.175 C1 VMP 17 VMP O5 O5 O 0 1 N N N 33.166 21.491 28.273 3.376 -0.778 0.557 O5 VMP 18 VMP C5 C5 C 0 1 N N R 32.112 20.869 27.504 4.703 -1.132 0.163 C5 VMP 19 VMP C6 C6 C 0 1 N N N 32.061 19.397 27.944 5.180 -2.328 0.990 C6 VMP 20 VMP O6 O6 O 0 1 N N N 33.145 18.675 27.349 4.377 -3.469 0.682 O6 VMP 21 VMP C4 C4 C 0 1 N N S 32.356 21.034 25.982 5.638 0.058 0.400 C4 VMP 22 VMP O4 O4 O 0 1 N N N 31.214 20.555 25.264 6.954 -0.273 -0.046 O4 VMP 23 VMP C3 C3 C 0 1 N N S 32.639 22.504 25.602 5.121 1.268 -0.383 C3 VMP 24 VMP O3 O3 O 0 1 N N N 33.125 22.570 24.261 5.945 2.402 -0.110 O3 VMP 25 VMP C2 C2 C 0 1 N N R 33.670 23.136 26.567 3.681 1.565 0.049 C2 VMP 26 VMP O2 O2 O 0 1 N N N 33.841 24.532 26.296 3.163 2.647 -0.728 O2 VMP 27 VMP H10 H10 H 0 1 N N N 36.465 26.560 31.192 -4.175 -1.213 -1.648 H10 VMP 28 VMP H24 H24 H 0 1 N N N 38.602 27.695 31.283 -6.624 -1.516 -1.859 H24 VMP 29 VMP H26 H26 H 0 1 N N N 40.512 28.567 32.600 -8.868 -1.050 -1.035 H26 VMP 30 VMP H27 H27 H 0 1 N N N 40.548 28.303 35.059 -9.215 0.382 0.932 H27 VMP 31 VMP H25 H25 H 0 1 N N N 38.682 27.166 36.222 -7.325 1.370 2.108 H25 VMP 32 VMP H13 H13 H 0 1 N N N 36.538 26.039 36.136 -4.884 1.681 2.324 H13 VMP 33 VMP H14 H14 H 0 1 N N N 34.631 25.173 34.818 -2.635 1.231 1.522 H14 VMP 34 VMP H2 H2 H 0 1 N N N 35.493 24.634 30.693 -0.997 0.829 0.842 H2 VMP 35 VMP H1 H1 H 0 1 N N N 35.100 23.581 28.846 1.306 1.138 1.065 H1 VMP 36 VMP HA HA H 0 1 N N N 32.202 23.350 28.130 2.805 0.073 -1.237 HA VMP 37 VMP HB HB H 0 1 N N N 34.629 22.614 26.431 3.666 1.833 1.105 HB VMP 38 VMP H5 H5 H 0 1 N N N 31.148 21.339 27.751 4.711 -1.395 -0.894 H5 VMP 39 VMP H61C H61C H 0 0 N N N 32.142 19.340 29.040 6.222 -2.541 0.753 H61C VMP 40 VMP H62C H62C H 0 0 N N N 31.107 18.953 27.624 5.088 -2.095 2.052 H62C VMP 41 VMP H4 H4 H 0 1 N N N 33.239 20.436 25.712 5.663 0.295 1.464 H4 VMP 42 VMP H6 H6 H 0 1 N N N 33.109 17.766 27.624 4.624 -4.266 1.171 H6 VMP 43 VMP HC HC H 0 1 N N N 31.361 20.655 24.331 7.600 0.436 0.074 HC VMP 44 VMP H3 H3 H 0 1 N N N 31.699 23.069 25.686 5.144 1.048 -1.451 H3 VMP 45 VMP HD HD H 0 1 N N N 33.298 23.475 24.031 5.675 3.206 -0.574 HD VMP 46 VMP H2A H2A H 0 1 N N N 34.124 24.648 25.397 2.252 2.886 -0.510 H2A VMP 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 VMP C10 C11 SING Y N 1 VMP C10 C9 DOUB Y N 2 VMP C11 C24 SING Y N 3 VMP C11 C12 DOUB Y N 4 VMP C24 C26 DOUB Y N 5 VMP C26 C27 SING Y N 6 VMP C27 C25 DOUB Y N 7 VMP C25 C12 SING Y N 8 VMP C12 C13 SING Y N 9 VMP C13 C14 DOUB Y N 10 VMP C14 C9 SING Y N 11 VMP C9 C8 SING N N 12 VMP C8 O8 DOUB N N 13 VMP C8 N2 SING N N 14 VMP N2 C7 SING N N 15 VMP C7 O7 DOUB N N 16 VMP C7 N1 SING N N 17 VMP N1 C1 SING N N 18 VMP C1 O5 SING N N 19 VMP C1 C2 SING N N 20 VMP O5 C5 SING N N 21 VMP C5 C6 SING N N 22 VMP C5 C4 SING N N 23 VMP C6 O6 SING N N 24 VMP C4 O4 SING N N 25 VMP C4 C3 SING N N 26 VMP C3 O3 SING N N 27 VMP C3 C2 SING N N 28 VMP C2 O2 SING N N 29 VMP C10 H10 SING N N 30 VMP C24 H24 SING N N 31 VMP C26 H26 SING N N 32 VMP C27 H27 SING N N 33 VMP C25 H25 SING N N 34 VMP C13 H13 SING N N 35 VMP C14 H14 SING N N 36 VMP N2 H2 SING N N 37 VMP N1 H1 SING N N 38 VMP C1 HA SING N N 39 VMP C2 HB SING N N 40 VMP C5 H5 SING N N 41 VMP C6 H61C SING N N 42 VMP C6 H62C SING N N 43 VMP C4 H4 SING N N 44 VMP O6 H6 SING N N 45 VMP O4 HC SING N N 46 VMP C3 H3 SING N N 47 VMP O3 HD SING N N 48 VMP 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 VMP SMILES ACDLabs 12.01 "O=C(NC1OC(C(O)C(O)C1O)CO)NC(=O)c3cc2ccccc2cc3" VMP 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)11-6-5-9-3-1-2-4-10(9)7-11/h1-7,12-15,17,21-24H,8H2,(H2,19,20,25,26)/t12-,13-,14+,15-,17-/m1/s1" VMP InChIKey InChI 1.03 CWTXJPICSREUOK-OWVAZHOYSA-N VMP SMILES_CANONICAL CACTVS 3.385 "OC[C@H]1O[C@@H](NC(=O)NC(=O)c2ccc3ccccc3c2)[C@H](O)[C@@H](O)[C@@H]1O" VMP SMILES CACTVS 3.385 "OC[CH]1O[CH](NC(=O)NC(=O)c2ccc3ccccc3c2)[CH](O)[CH](O)[CH]1O" VMP SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc2cc(ccc2c1)C(=O)NC(=O)N[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O" VMP SMILES "OpenEye OEToolkits" 1.9.2 "c1ccc2cc(ccc2c1)C(=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 VMP "SYSTEMATIC NAME" ACDLabs 12.01 "N-[(naphthalen-2-ylcarbonyl)carbamoyl]-beta-D-glucopyranosylamine" VMP "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-2-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 VMP "Create component" 2012-11-21 EBI VMP "Initial release" 2013-12-11 RCSB VMP "Modify descriptor" 2014-09-05 RCSB #