data_MAR # _chem_comp.id MAR _chem_comp.name "4'-EPI-4'-(2-DEOXYFUCOSE)DAUNOMYCIN" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C33 H39 N O13" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "MAR70; DAUNOMYCIN DERIVATIVE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2020-06-17 _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 657.662 _chem_comp.one_letter_code ? _chem_comp.three_letter_code MAR _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1D35 _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 MAR C1 C1 C 0 1 Y N N 15.258 18.419 5.102 1.206 0.347 -7.667 C1 MAR 1 MAR C2 C2 C 0 1 Y N N 16.402 19.206 5.113 2.422 -0.106 -8.154 C2 MAR 2 MAR C3 C3 C 0 1 Y N N 17.727 18.632 5.102 3.410 -0.530 -7.290 C3 MAR 3 MAR C4 C4 C 0 1 Y N N 17.859 17.170 5.033 3.199 -0.508 -5.913 C4 MAR 4 MAR O4 O4 O 0 1 N N N 19.012 16.537 5.012 4.173 -0.925 -5.068 O4 MAR 5 MAR C5 C5 C 0 1 Y N N 16.630 16.450 5.023 1.977 -0.058 -5.409 C5 MAR 6 MAR C6 C6 C 0 1 N N N 16.715 14.951 4.938 1.732 -0.020 -3.955 C6 MAR 7 MAR O6 O6 O 0 1 N N N 17.758 14.285 4.890 2.653 -0.146 -3.171 O6 MAR 8 MAR C7 C7 C 0 1 Y N N 15.429 14.198 4.932 0.354 0.166 -3.463 C7 MAR 9 MAR C8 C8 C 0 1 Y N N 15.480 12.814 4.895 0.032 -0.080 -2.131 C8 MAR 10 MAR O8 O8 O 0 1 N N N 16.602 12.139 4.895 0.994 -0.496 -1.271 O8 MAR 11 MAR C9 C9 C 0 1 Y N N 14.243 12.117 4.864 -1.280 0.096 -1.673 C9 MAR 12 MAR C10 C10 C 0 1 N N S 14.316 10.548 4.890 -1.552 -0.198 -0.221 C10 MAR 13 MAR O10 O10 O 0 1 N N N 14.943 10.376 6.236 -0.487 0.326 0.572 O10 MAR 14 MAR C11 C11 C 0 1 N N N 13.006 9.876 4.773 -2.869 0.435 0.220 C11 MAR 15 MAR C12 C12 C 0 1 N N S 11.810 10.587 5.351 -3.960 0.029 -0.777 C12 MAR 16 MAR O12 O12 O 0 1 N N N 11.920 10.666 6.829 -5.240 0.420 -0.277 O12 MAR 17 MAR C13 C13 C 0 1 N N N 10.517 9.834 5.139 -3.929 -1.462 -0.985 C13 MAR 18 MAR O13 O13 O 0 1 N N N 9.879 10.025 4.101 -3.307 -1.931 -1.908 O13 MAR 19 MAR C14 C14 C 0 1 N N N 10.028 8.745 6.103 -4.675 -2.370 -0.041 C14 MAR 20 MAR C15 C15 C 0 1 N N N 11.675 12.069 4.858 -3.686 0.739 -2.101 C15 MAR 21 MAR C16 C16 C 0 1 Y N N 12.986 12.713 4.879 -2.259 0.520 -2.536 C16 MAR 22 MAR C17 C17 C 0 1 Y N N 12.986 14.119 4.922 -1.951 0.773 -3.880 C17 MAR 23 MAR O17 O17 O 0 1 N N N 11.760 14.777 4.932 -2.924 1.191 -4.727 O17 MAR 24 MAR C18 C18 C 0 1 Y N N 14.116 14.906 4.948 -0.652 0.598 -4.351 C18 MAR 25 MAR C19 C19 C 0 1 N N N 14.108 16.357 5.001 -0.317 0.858 -5.763 C19 MAR 26 MAR O19 O19 O 0 1 N N N 13.067 17.032 5.007 -1.094 1.461 -6.479 O19 MAR 27 MAR C20 C20 C 0 1 Y N N 15.396 17.027 5.023 0.974 0.377 -6.298 C20 MAR 28 MAR C21 C21 C 0 1 N N N 20.277 17.336 5.272 5.281 -1.323 -5.878 C21 MAR 29 MAR "C1'" C1* C 0 1 N N R 15.823 9.336 6.485 -0.091 -0.711 1.471 "C1'" MAR 30 MAR "C2'" C2* C 0 1 N N N 16.855 9.679 7.523 1.245 -0.342 2.118 "C2'" MAR 31 MAR "C3'" C3* C 0 1 N N S 16.200 9.842 8.927 1.089 0.988 2.863 "C3'" MAR 32 MAR "N3'" N3* N 0 1 N N N 17.330 10.044 9.944 2.318 1.279 3.613 "N3'" MAR 33 MAR "C4'" C4* C 0 1 N N S 15.407 8.577 9.261 -0.093 0.873 3.830 "C4'" MAR 34 MAR "O4'" O4* O 0 1 N N N 16.374 7.500 9.473 0.214 -0.078 4.851 "O4'" MAR 35 MAR "C5'" C5* C 0 1 N N S 14.341 8.329 8.217 -1.329 0.412 3.054 "C5'" MAR 36 MAR "O5'" O5* O 0 1 N N N 15.047 8.132 6.882 -1.087 -0.869 2.480 "O5'" MAR 37 MAR "C6'" C6* C 0 1 N N N 13.531 7.024 8.366 -2.524 0.325 4.006 "C6'" MAR 38 MAR CB1 CB1 C 0 1 N N S 15.958 6.462 10.358 -0.312 0.442 6.073 CB1 MAR 39 MAR CB2 CB2 C 0 1 N N N 16.580 5.152 10.013 -0.355 -0.669 7.124 CB2 MAR 40 MAR CB3 CB3 C 0 1 N N S 18.101 5.062 10.342 1.062 -1.213 7.334 CB3 MAR 41 MAR OB3 OB3 O 0 1 N N N 18.365 3.597 10.188 1.061 -2.148 8.415 OB3 MAR 42 MAR CB4 CB4 C 0 1 N N R 18.354 5.531 11.777 1.993 -0.041 7.662 CB4 MAR 43 MAR OB4 OB4 O 0 1 N N N 19.813 5.427 11.995 3.344 -0.504 7.717 OB4 MAR 44 MAR CB5 CB5 C 0 1 N N S 17.806 6.926 11.984 1.859 1.023 6.571 CB5 MAR 45 MAR OB5 OB5 O 0 1 N N N 16.324 6.864 11.735 0.519 1.506 6.533 OB5 MAR 46 MAR CB6 CB6 C 0 1 N N N 17.904 7.435 13.446 2.809 2.183 6.874 CB6 MAR 47 MAR H1 H1 H 0 1 N N N 14.261 18.889 5.154 0.439 0.677 -8.352 H1 MAR 48 MAR H2 H2 H 0 1 N N N 16.256 20.299 5.130 2.597 -0.129 -9.219 H2 MAR 49 MAR H3 H3 H 0 1 N N N 18.611 19.290 5.145 4.353 -0.881 -7.683 H3 MAR 50 MAR HO8 HO8 H 0 1 N N N 16.637 11.190 4.869 1.056 -1.456 -1.363 HO8 MAR 51 MAR H10 H10 H 0 1 N N N 14.863 10.091 4.032 -1.609 -1.278 -0.078 H10 MAR 52 MAR H111 1H11 H 0 0 N N N 12.809 9.632 3.702 -2.768 1.521 0.232 H111 MAR 53 MAR H112 2H11 H 0 0 N N N 13.074 8.852 5.210 -3.132 0.080 1.216 H112 MAR 54 MAR HO12 2HO1 H 0 0 N N N 11.165 11.114 7.193 -5.891 0.162 -0.944 HO12 MAR 55 MAR H141 1H14 H 0 0 N N N 9.074 8.189 5.946 -4.537 -3.406 -0.349 H141 MAR 56 MAR H142 2H14 H 0 0 N N N 10.843 7.991 6.200 -4.290 -2.237 0.969 H142 MAR 57 MAR H143 3H14 H 0 0 N N N 9.994 9.190 7.124 -5.736 -2.123 -0.062 H143 MAR 58 MAR H151 1H15 H 0 0 N N N 11.188 12.136 3.856 -3.864 1.807 -1.980 H151 MAR 59 MAR H152 2H15 H 0 0 N N N 10.916 12.639 5.443 -4.358 0.348 -2.865 H152 MAR 60 MAR HO17 7HO1 H 0 0 N N N 11.760 15.726 4.961 -3.319 0.397 -5.112 HO17 MAR 61 MAR H211 1H21 H 0 0 N N N 21.254 16.799 5.254 6.093 -1.668 -5.239 H211 MAR 62 MAR H212 2H21 H 0 0 N N N 20.319 18.192 4.558 4.974 -2.130 -6.543 H212 MAR 63 MAR H213 3H21 H 0 0 N N N 20.174 17.872 6.244 5.621 -0.474 -6.471 H213 MAR 64 MAR "H1'" H1* H 0 1 N N N 16.390 9.132 5.547 0.017 -1.646 0.921 "H1'" MAR 65 MAR "H2'1" 1H2* H 0 0 N N N 17.685 8.934 7.539 1.537 -1.122 2.822 "H2'1" MAR 66 MAR "H2'2" 2H2* H 0 0 N N N 17.443 10.581 7.236 2.008 -0.241 1.346 "H2'2" MAR 67 MAR "H3'" H3* H 0 1 N N N 15.504 10.713 8.948 0.900 1.787 2.147 "H3'" MAR 68 MAR "HN'1" 1HN* H 0 0 N N N 16.901 10.150 10.863 3.065 1.332 2.937 "HN'1" MAR 69 MAR "HN'2" 2HN* H 0 0 N N N 17.948 10.818 9.702 2.209 2.205 3.999 "HN'2" MAR 70 MAR "H4'" H4* H 0 1 N N N 14.820 8.667 10.204 -0.289 1.844 4.284 "H4'" MAR 71 MAR "H5'" H5* H 0 1 N N N 13.650 9.199 8.313 -1.548 1.128 2.262 "H5'" MAR 72 MAR "H6'1" 1H6* H 0 0 N N N 12.745 6.841 7.596 -3.422 0.078 3.440 "H6'1" MAR 73 MAR "H6'2" 2H6* H 0 0 N N N 14.225 6.152 8.410 -2.340 -0.448 4.751 "H6'2" MAR 74 MAR "H6'3" 3H6* H 0 0 N N N 13.079 6.974 9.384 -2.661 1.284 4.505 "H6'3" MAR 75 MAR HB1 HB1 H 0 1 N N N 14.855 6.322 10.267 -1.320 0.818 5.902 HB1 MAR 76 MAR HB21 1HB2 H 0 0 N N N 16.025 4.316 10.499 -0.735 -0.269 8.063 HB21 MAR 77 MAR HB22 2HB2 H 0 0 N N N 16.396 4.902 8.941 -1.006 -1.472 6.778 HB22 MAR 78 MAR HB3 HB3 H 0 1 N N N 18.755 5.696 9.699 1.402 -1.707 6.424 HB3 MAR 79 MAR HOB3 3HOB H 0 0 N N N 19.292 3.542 10.388 0.455 -2.859 8.169 HOB3 MAR 80 MAR HB4 HB4 H 0 1 N N N 17.824 4.902 12.530 1.715 0.386 8.626 HB4 MAR 81 MAR HOB4 4HOB H 0 0 N N N 19.970 5.718 12.885 3.894 0.262 7.926 HOB4 MAR 82 MAR HB5 HB5 H 0 1 N N N 18.394 7.593 11.311 2.115 0.587 5.606 HB5 MAR 83 MAR HB61 1HB6 H 0 0 N N N 17.500 8.463 13.598 2.714 2.942 6.097 HB61 MAR 84 MAR HB62 2HB6 H 0 0 N N N 17.415 6.715 14.143 2.555 2.619 7.840 HB62 MAR 85 MAR HB63 3HB6 H 0 0 N N N 18.954 7.369 13.812 3.835 1.816 6.899 HB63 MAR 86 # # 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 MAR C1 C2 DOUB Y N 1 MAR C1 C20 SING Y N 2 MAR C1 H1 SING N N 3 MAR C2 C3 SING Y N 4 MAR C2 H2 SING N N 5 MAR C3 C4 DOUB Y N 6 MAR C3 H3 SING N N 7 MAR C4 O4 SING N N 8 MAR C4 C5 SING Y N 9 MAR O4 C21 SING N N 10 MAR C5 C6 SING N N 11 MAR C5 C20 DOUB Y N 12 MAR C6 O6 DOUB N N 13 MAR C6 C7 SING N N 14 MAR C7 C8 DOUB Y N 15 MAR C7 C18 SING Y N 16 MAR C8 O8 SING N N 17 MAR C8 C9 SING Y N 18 MAR O8 HO8 SING N N 19 MAR C9 C10 SING N N 20 MAR C9 C16 DOUB Y N 21 MAR C10 O10 SING N N 22 MAR C10 C11 SING N N 23 MAR C10 H10 SING N N 24 MAR O10 "C1'" SING N N 25 MAR C11 C12 SING N N 26 MAR C11 H111 SING N N 27 MAR C11 H112 SING N N 28 MAR C12 O12 SING N N 29 MAR C12 C13 SING N N 30 MAR C12 C15 SING N N 31 MAR O12 HO12 SING N N 32 MAR C13 O13 DOUB N N 33 MAR C13 C14 SING N N 34 MAR C14 H141 SING N N 35 MAR C14 H142 SING N N 36 MAR C14 H143 SING N N 37 MAR C15 C16 SING N N 38 MAR C15 H151 SING N N 39 MAR C15 H152 SING N N 40 MAR C16 C17 SING Y N 41 MAR C17 O17 SING N N 42 MAR C17 C18 DOUB Y N 43 MAR O17 HO17 SING N N 44 MAR C18 C19 SING N N 45 MAR C19 O19 DOUB N N 46 MAR C19 C20 SING N N 47 MAR C21 H211 SING N N 48 MAR C21 H212 SING N N 49 MAR C21 H213 SING N N 50 MAR "C1'" "C2'" SING N N 51 MAR "C1'" "O5'" SING N N 52 MAR "C1'" "H1'" SING N N 53 MAR "C2'" "C3'" SING N N 54 MAR "C2'" "H2'1" SING N N 55 MAR "C2'" "H2'2" SING N N 56 MAR "C3'" "N3'" SING N N 57 MAR "C3'" "C4'" SING N N 58 MAR "C3'" "H3'" SING N N 59 MAR "N3'" "HN'1" SING N N 60 MAR "N3'" "HN'2" SING N N 61 MAR "C4'" "O4'" SING N N 62 MAR "C4'" "C5'" SING N N 63 MAR "C4'" "H4'" SING N N 64 MAR "O4'" CB1 SING N N 65 MAR "C5'" "O5'" SING N N 66 MAR "C5'" "C6'" SING N N 67 MAR "C5'" "H5'" SING N N 68 MAR "C6'" "H6'1" SING N N 69 MAR "C6'" "H6'2" SING N N 70 MAR "C6'" "H6'3" SING N N 71 MAR CB1 CB2 SING N N 72 MAR CB1 OB5 SING N N 73 MAR CB1 HB1 SING N N 74 MAR CB2 CB3 SING N N 75 MAR CB2 HB21 SING N N 76 MAR CB2 HB22 SING N N 77 MAR CB3 OB3 SING N N 78 MAR CB3 CB4 SING N N 79 MAR CB3 HB3 SING N N 80 MAR OB3 HOB3 SING N N 81 MAR CB4 OB4 SING N N 82 MAR CB4 CB5 SING N N 83 MAR CB4 HB4 SING N N 84 MAR OB4 HOB4 SING N N 85 MAR CB5 OB5 SING N N 86 MAR CB5 CB6 SING N N 87 MAR CB5 HB5 SING N N 88 MAR CB6 HB61 SING N N 89 MAR CB6 HB62 SING N N 90 MAR CB6 HB63 SING N N 91 # # 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 MAR SMILES ACDLabs 10.04 "O=C2c1c(O)c6c(c(O)c1C(=O)c3cccc(OC)c23)CC(O)(C(=O)C)CC6OC5OC(C(OC4OC(C(O)C(O)C4)C)C(N)C5)C" MAR SMILES_CANONICAL CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O[C@H]6C[C@H](O)[C@@H](O)[C@H](C)O6)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O" MAR SMILES CACTVS 3.341 "COc1cccc2C(=O)c3c(O)c4C[C](O)(C[CH](O[CH]5C[CH](N)[CH](O[CH]6C[CH](O)[CH](O)[CH](C)O6)[CH](C)O5)c4c(O)c3C(=O)c12)C(C)=O" MAR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@@H]2[C@@H](O[C@H](C[C@@H]2N)O[C@H]3C[C@@](Cc4c3c(c5c(c4O)C(=O)c6cccc(c6C5=O)OC)O)(C(=O)C)O)C)O)O" MAR SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(CC(O1)OC2C(OC(CC2N)OC3CC(Cc4c3c(c5c(c4O)C(=O)c6cccc(c6C5=O)OC)O)(C(=O)C)O)C)O)O" MAR InChI InChI 1.03 "InChI=1S/C33H39NO13/c1-12-27(37)18(36)9-22(44-12)47-32-13(2)45-21(8-17(32)34)46-20-11-33(42,14(3)35)10-16-24(20)31(41)26-25(29(16)39)28(38)15-6-5-7-19(43-4)23(15)30(26)40/h5-7,12-13,17-18,20-22,27,32,36-37,39,41-42H,8-11,34H2,1-4H3/t12-,13-,17-,18-,20-,21-,22-,27-,32+,33-/m0/s1" MAR InChIKey InChI 1.03 QTGKDZKONUUXOU-NIGIIATCSA-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 MAR "SYSTEMATIC NAME" ACDLabs 10.04 "(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-(2,6-dideoxy-alpha-L-arabino-hexopyranosyl)-alpha-L-lyxo-hexopyranoside" MAR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-[(2S,4S,5R,6S)-4,5-dihydroxy-6-methyl-oxan-2-yl]oxy-6-methyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site MAR "Create component" 1999-07-08 RCSB MAR "Modify descriptor" 2011-06-04 RCSB MAR "Modify synonyms" 2020-06-05 PDBE # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 MAR MAR70 ? ? 2 MAR "DAUNOMYCIN DERIVATIVE" ? ? ##