data_VAW # _chem_comp.id VAW _chem_comp.name "(2S,3R,4S)-methyl 4-(2-(2-(1H-indol-3-yl)ethylamino)ethyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H36 N2 O9" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-{[2-(1H-indol-3-yl)ethyl]amino}ethyl)-3,4-dihydro-2H-pyran-5-carboxylate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2007-09-04 _chem_comp.pdbx_modified_date 2021-03-13 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 532.583 _chem_comp.one_letter_code ? _chem_comp.three_letter_code VAW _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 2VAQ _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # # 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 VAW CBD CBD C 0 1 Y N N 100.814 -0.510 -0.282 -6.993 -1.069 0.443 CBD VAW 1 VAW CAM CAM C 0 1 Y N N 101.808 -1.446 -0.547 -6.958 -0.696 1.788 CAM VAW 2 VAW CAK CAK C 0 1 Y N N 101.829 -2.687 0.098 -7.706 -1.382 2.702 CAK VAW 3 VAW CAJ CAJ C 0 1 Y N N 100.843 -3.006 1.020 -8.501 -2.449 2.305 CAJ VAW 4 VAW CAL CAL C 0 1 Y N N 99.841 -2.076 1.288 -8.550 -2.834 0.983 CAL VAW 5 VAW CBC CBC C 0 1 Y N N 99.831 -0.837 0.641 -7.797 -2.149 0.035 CBC VAW 6 VAW NAU NAU N 0 1 Y N N 99.010 0.212 0.725 -7.635 -2.285 -1.326 NAU VAW 7 VAW CAN CAN C 0 1 Y N N 99.422 1.169 -0.116 -6.764 -1.336 -1.787 CAN VAW 8 VAW CBB CBB C 0 1 Y N N 100.524 0.781 -0.745 -6.344 -0.567 -0.771 CBB VAW 9 VAW CAR CAR C 0 1 N N N 101.264 1.641 -1.765 -5.386 0.593 -0.860 CAR VAW 10 VAW CAP CAP C 0 1 N N N 102.394 2.459 -1.133 -4.167 0.163 -0.698 CAP VAW 11 VAW NAT NAT N 0 1 N N N 102.792 1.887 0.179 -3.233 1.293 -0.785 NAT VAW 12 VAW CAQ CAQ C 0 1 N N N 104.225 1.641 0.066 -1.860 0.867 -0.481 CAQ VAW 13 VAW CAS CAS C 0 1 N N N 104.933 1.571 1.408 -1.077 1.909 -0.456 CAS VAW 14 VAW CBJ CBJ C 0 1 N N S 104.559 0.258 2.031 0.363 1.459 -0.202 CBJ VAW 15 VAW CBH CBH C 0 1 N N R 105.573 -0.877 1.913 0.795 0.487 -1.305 CBH VAW 16 VAW CAH CAH C 0 1 N N N 105.619 -1.542 0.538 0.433 1.055 -2.653 CAH VAW 17 VAW CAA CAA C 0 1 N N N 105.979 -0.831 -0.592 -0.380 0.399 -3.443 CAA VAW 18 VAW CBA CBA C 0 1 N N N 104.392 0.363 3.540 1.271 2.658 -0.204 CBA VAW 19 VAW CAZ CAZ C 0 1 N N N 103.075 0.914 4.062 0.845 3.836 0.456 CAZ VAW 20 VAW OAC OAC O 0 1 N N N 102.809 1.004 5.276 1.505 4.854 0.369 OAC VAW 21 VAW OAV OAV O 0 1 N N N 102.256 1.338 3.022 -0.292 3.829 1.183 OAV VAW 22 VAW CAB CAB C 0 1 N N N 100.960 0.815 2.855 -0.721 5.078 1.727 CAB VAW 23 VAW CAI CAI C 0 1 N N N 105.401 -0.118 4.367 2.464 2.652 -0.804 CAI VAW 24 VAW OAW OAW O 0 1 N N N 106.596 -0.638 3.893 2.948 1.586 -1.461 OAW VAW 25 VAW CBK CBK C 0 1 N N S 106.915 -0.451 2.520 2.316 0.301 -1.213 CBK VAW 26 VAW O1 O1 O 0 1 N N N 107.930 -1.423 2.431 2.667 -0.164 0.092 O1 VAW 27 VAW C1 C1 C 0 1 N N S 109.168 -0.988 2.981 4.053 -0.477 0.245 C1 VAW 28 VAW O5 O5 O 0 1 N N N 109.818 -0.021 2.160 4.387 -1.582 -0.597 O5 VAW 29 VAW C5 C5 C 0 1 N N R 110.922 0.504 2.819 5.764 -1.963 -0.540 C5 VAW 30 VAW C6 C6 C 0 1 N N N 111.352 1.774 2.092 6.010 -3.131 -1.497 C6 VAW 31 VAW O6 O6 O 0 1 N N N 111.525 1.582 0.666 5.792 -2.700 -2.841 O6 VAW 32 VAW C4 C4 C 0 1 N N S 111.989 -0.577 2.753 6.115 -2.389 0.888 C4 VAW 33 VAW O4 O4 O 0 1 N N N 112.984 -0.201 3.654 7.505 -2.715 0.960 O4 VAW 34 VAW C3 C3 C 0 1 N N S 111.468 -1.930 3.251 5.809 -1.235 1.847 C3 VAW 35 VAW O3 O3 O 0 1 N N N 112.347 -2.990 2.881 6.065 -1.649 3.191 O3 VAW 36 VAW C2 C2 C 0 1 N N R 110.046 -2.207 2.737 4.335 -0.843 1.704 C2 VAW 37 VAW O2 O2 O 0 1 N N N 109.483 -3.362 3.379 4.056 0.280 2.541 O2 VAW 38 VAW HAM HAM H 0 1 N N N 102.579 -1.210 -1.265 -6.342 0.133 2.104 HAM VAW 39 VAW HAK HAK H 0 1 N N N 102.613 -3.397 -0.122 -7.678 -1.093 3.742 HAK VAW 40 VAW HAJ HAJ H 0 1 N N N 100.852 -3.962 1.523 -9.086 -2.983 3.039 HAJ VAW 41 VAW HAL HAL H 0 1 N N N 99.066 -2.314 2.001 -9.171 -3.666 0.684 HAL VAW 42 VAW HAU HAU H 0 1 N N N 98.211 0.274 1.323 -8.072 -2.954 -1.875 HAU VAW 43 VAW HAN HAN H 0 1 N N N 98.929 2.119 -0.261 -6.462 -1.221 -2.818 HAN VAW 44 VAW HAR1 1HAR H 0 0 N N N 101.698 0.979 -2.529 -5.478 1.065 -1.838 HAR1 VAW 45 VAW HAR2 2HAR H 0 0 N N N 100.540 2.347 -2.198 -5.622 1.320 -0.082 HAR2 VAW 46 VAW HAP1 1HAP H 0 0 N N N 103.263 2.449 -1.807 -4.075 -0.309 0.280 HAP1 VAW 47 VAW HAP2 2HAP H 0 0 N N N 102.039 3.488 -0.976 -3.931 -0.564 -1.475 HAP2 VAW 48 VAW HAT HAT H 0 1 N N N 102.596 2.526 0.922 -3.282 1.734 -1.691 HAT VAW 49 VAW HAQ1 1HAQ H 0 0 N N N 104.369 0.679 -0.448 -1.839 0.373 0.490 HAQ1 VAW 50 VAW HAQ2 2HAQ H 0 0 N N N 104.659 2.486 -0.489 -1.517 0.174 -1.249 HAQ2 VAW 51 VAW HAS1 1HAS H 0 0 N N N 106.022 1.632 1.269 -1.132 2.429 -1.412 HAS1 VAW 52 VAW HAS2 2HAS H 0 0 N N N 104.635 2.410 2.053 -1.393 2.581 0.342 HAS2 VAW 53 VAW HBJ HBJ H 0 1 N N N 103.645 0.030 1.463 0.423 0.960 0.765 HBJ VAW 54 VAW HBH HBH H 0 1 N N N 105.226 -1.721 2.527 0.298 -0.473 -1.165 HBH VAW 55 VAW HAH HAH H 0 1 N N N 105.365 -2.588 0.447 0.845 2.002 -2.968 HAH VAW 56 VAW HBK HBK H 0 1 N N N 107.243 0.503 2.081 2.644 -0.421 -1.961 HBK VAW 57 VAW HAA1 1HAA H 0 0 N N N 105.938 -1.507 -1.433 -0.640 0.806 -4.409 HAA1 VAW 58 VAW HAA2 2HAA H 0 0 N N N 106.252 0.213 -0.627 -0.792 -0.549 -3.128 HAA2 VAW 59 VAW HAI HAI H 0 1 N N N 105.246 -0.085 5.435 3.067 3.547 -0.760 HAI VAW 60 VAW HAB1 1HAB H 0 0 N N N 100.489 0.679 3.840 0.082 5.509 2.326 HAB1 VAW 61 VAW HAB2 2HAB H 0 0 N N N 100.358 1.513 2.255 -0.975 5.761 0.916 HAB2 VAW 62 VAW HAB3 3HAB H 0 0 N N N 101.020 -0.155 2.340 -1.598 4.919 2.356 HAB3 VAW 63 VAW H1 H1 H 0 1 N N N 109.020 -0.600 3.999 4.653 0.389 -0.036 H1 VAW 64 VAW H2 H2 H 0 1 N N N 110.096 -2.410 1.657 3.705 -1.683 1.997 H2 VAW 65 VAW H5 H5 H 0 1 N N N 110.723 0.774 3.867 6.387 -1.117 -0.831 H5 VAW 66 VAW H6C1 1H6C H 0 0 N N N 110.576 2.539 2.246 7.037 -3.479 -1.388 H6C1 VAW 67 VAW H6C2 2H6C H 0 0 N N N 112.326 2.077 2.505 5.324 -3.945 -1.261 H6C2 VAW 68 VAW H4 H4 H 0 1 N N N 112.326 -0.678 1.711 5.522 -3.261 1.164 H4 VAW 69 VAW H6 H6 H 0 1 N N N 111.563 2.427 0.234 5.931 -3.391 -3.503 H6 VAW 70 VAW HA HA H 0 1 N N N 113.811 -0.115 3.195 7.798 -2.994 1.839 HA VAW 71 VAW H3 H3 H 0 1 N N N 111.431 -1.881 4.349 6.441 -0.380 1.602 H3 VAW 72 VAW HB HB H 0 1 N N N 112.542 -2.931 1.953 5.893 -0.966 3.853 HB VAW 73 VAW HC HC H 0 1 N N N 109.359 -4.052 2.738 3.140 0.586 2.497 HC VAW 74 # # 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 VAW CBD CAM SING Y N 1 VAW CBD CBC DOUB Y N 2 VAW CBD CBB SING Y N 3 VAW CAM CAK DOUB Y N 4 VAW CAK CAJ SING Y N 5 VAW CAJ CAL DOUB Y N 6 VAW CAL CBC SING Y N 7 VAW CBC NAU SING Y N 8 VAW NAU CAN SING Y N 9 VAW CAN CBB DOUB Y N 10 VAW CBB CAR SING N N 11 VAW CAR CAP SING N N 12 VAW CAP NAT SING N N 13 VAW NAT CAQ SING N N 14 VAW CAQ CAS SING N N 15 VAW CAS CBJ SING N N 16 VAW CBJ CBH SING N N 17 VAW CBJ CBA SING N N 18 VAW CBH CAH SING N N 19 VAW CBH CBK SING N N 20 VAW CAH CAA DOUB N N 21 VAW CBA CAZ SING N N 22 VAW CBA CAI DOUB N N 23 VAW CAZ OAC DOUB N N 24 VAW CAZ OAV SING N N 25 VAW OAV CAB SING N N 26 VAW CAI OAW SING N N 27 VAW OAW CBK SING N N 28 VAW CBK O1 SING N N 29 VAW O1 C1 SING N N 30 VAW C1 O5 SING N N 31 VAW C1 C2 SING N N 32 VAW O5 C5 SING N N 33 VAW C5 C6 SING N N 34 VAW C5 C4 SING N N 35 VAW C6 O6 SING N N 36 VAW C4 O4 SING N N 37 VAW C4 C3 SING N N 38 VAW C3 O3 SING N N 39 VAW C3 C2 SING N N 40 VAW C2 O2 SING N N 41 VAW CAM HAM SING N N 42 VAW CAK HAK SING N N 43 VAW CAJ HAJ SING N N 44 VAW CAL HAL SING N N 45 VAW NAU HAU SING N N 46 VAW CAN HAN SING N N 47 VAW CAR HAR1 SING N N 48 VAW CAR HAR2 SING N N 49 VAW CAP HAP1 SING N N 50 VAW CAP HAP2 SING N N 51 VAW NAT HAT SING N N 52 VAW CAQ HAQ1 SING N N 53 VAW CAQ HAQ2 SING N N 54 VAW CAS HAS1 SING N N 55 VAW CAS HAS2 SING N N 56 VAW CBJ HBJ SING N N 57 VAW CBH HBH SING N N 58 VAW CAH HAH SING N N 59 VAW CBK HBK SING N N 60 VAW CAA HAA1 SING N N 61 VAW CAA HAA2 SING N N 62 VAW CAI HAI SING N N 63 VAW CAB HAB1 SING N N 64 VAW CAB HAB2 SING N N 65 VAW CAB HAB3 SING N N 66 VAW C1 H1 SING N N 67 VAW C2 H2 SING N N 68 VAW C5 H5 SING N N 69 VAW C6 H6C1 SING N N 70 VAW C6 H6C2 SING N N 71 VAW C4 H4 SING N N 72 VAW O6 H6 SING N N 73 VAW O4 HA SING N N 74 VAW C3 H3 SING N N 75 VAW O3 HB SING N N 76 VAW O2 HC SING N N 77 # # 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 VAW SMILES ACDLabs 10.04 "O=C(OC)C2=COC(OC1OC(C(O)C(O)C1O)CO)C(\C=C)C2CCNCCc4c3ccccc3nc4" VAW SMILES_CANONICAL CACTVS 3.341 "COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CCNCCc3c[nH]c4ccccc34" VAW SMILES CACTVS 3.341 "COC(=O)C1=CO[CH](O[CH]2O[CH](CO)[CH](O)[CH](O)[CH]2O)[CH](C=C)[CH]1CCNCCc3c[nH]c4ccccc34" VAW SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CCNCCc2c[nH]c3c2cccc3)C=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O" VAW SMILES "OpenEye OEToolkits" 1.5.0 "COC(=O)C1=COC(C(C1CCNCCc2c[nH]c3c2cccc3)C=C)OC4C(C(C(C(O4)CO)O)O)O" VAW InChI InChI 1.03 "InChI=1S/C27H36N2O9/c1-3-16-18(9-11-28-10-8-15-12-29-20-7-5-4-6-17(15)20)19(25(34)35-2)14-36-26(16)38-27-24(33)23(32)22(31)21(13-30)37-27/h3-7,12,14,16,18,21-24,26-33H,1,8-11,13H2,2H3/t16-,18+,21-,22-,23+,24-,26+,27+/m1/s1" VAW InChIKey InChI 1.03 MYFRJCYMRYXZQB-JVARDMDOSA-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 VAW "SYSTEMATIC NAME" ACDLabs 10.04 "methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-{[2-(1H-indol-3-yl)ethyl]amino}ethyl)-3,4-dihydro-2H-pyran-5-carboxylate" VAW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (4S,5R,6S)-5-ethenyl-4-[2-[2-(1H-indol-3-yl)ethylamino]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-4H-pyran-3-carboxylate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site VAW "Create component" 2007-09-04 PDBJ VAW "Modify aromatic_flag" 2011-06-04 RCSB VAW "Modify descriptor" 2011-06-04 RCSB VAW "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id VAW _pdbx_chem_comp_synonyms.name "methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-{[2-(1H-indol-3-yl)ethyl]amino}ethyl)-3,4-dihydro-2H-pyran-5-carboxylate" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##