data_44D # _chem_comp.id 44D _chem_comp.name "7-[5-(4-AMINO-5-HYDROXY-6-METHYL-TETRAHYDRO-PYRAN-2-YLOXY)-4-HYDROXY-6-METHYL-TETRAHYDRO-PYRAN-2-YLOXY]-6,9,11-TRIHYDROXY-9-(2-HYDROXY-ACETYL)-7,8,9,10-TETRAHYDRO-NAPHTHACENE-5,12-DIONE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C32 H37 N O13" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "4'-(O-ALPHA-L-DAUNOSAMINYL)-4-DEMETHOXYDOXORUBICIN" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-12-16 _chem_comp.pdbx_modified_date 2021-03-01 _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 643.635 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 44D _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 1NAB _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 44D C1 C1 C 0 1 Y N N 2.560 18.262 20.318 -8.048 -2.158 -0.120 C1 44D 1 44D C2 C2 C 0 1 Y N N 3.535 19.117 20.992 -8.368 -3.497 0.023 C2 44D 2 44D C3 C3 C 0 1 Y N N 4.337 19.899 20.160 -7.391 -4.421 0.347 C3 44D 3 44D C4 C4 C 0 1 Y N N 4.220 19.873 18.755 -6.080 -4.020 0.533 C4 44D 4 44D C5 C5 C 0 1 N N N 3.161 18.992 16.776 -4.344 -2.231 0.584 C5 44D 5 44D C6 C6 C 0 1 Y N N 2.125 18.039 14.860 -2.612 -0.523 0.036 C6 44D 6 44D C7 C7 C 0 1 N N S 1.085 17.230 12.825 -0.778 1.077 -0.471 C7 44D 7 44D C8 C8 C 0 1 N N N 0.064 16.217 12.327 -0.536 2.310 -1.339 C8 44D 8 44D C9 C9 C 0 1 N N S 0.076 14.886 13.020 -1.452 3.436 -0.843 C9 44D 9 44D C10 C10 C 0 1 N N N -0.423 15.234 14.488 -2.893 3.071 -1.192 C10 44D 10 44D C11 C11 C 0 1 Y N N 0.518 16.394 16.461 -4.574 1.333 -0.618 C11 44D 11 44D C12 C12 C 0 1 N N N 1.573 17.381 18.389 -6.372 -0.312 -0.086 C12 44D 12 44D C13 C13 C 0 1 N N N -1.032 14.031 12.327 -1.312 3.584 0.650 C13 44D 13 44D C14 C14 C 0 1 N N N -0.794 12.610 12.018 -0.192 4.414 1.223 C14 44D 14 44D C15 C15 C 0 1 Y N N 2.492 18.281 18.925 -6.734 -1.739 0.063 C15 44D 15 44D C16 C16 C 0 1 Y N N 3.259 19.068 18.143 -5.741 -2.679 0.392 C16 44D 16 44D C17 C17 C 0 1 Y N N 2.238 18.111 16.234 -3.953 -0.882 0.137 C17 44D 17 44D C18 C18 C 0 1 Y N N 1.422 17.275 17.009 -4.950 0.061 -0.193 C18 44D 18 44D C19 C19 C 0 1 Y N N 0.386 16.345 15.068 -3.219 1.678 -0.718 C19 44D 19 44D C20 C20 C 0 1 Y N N 1.183 17.162 14.324 -2.250 0.763 -0.394 C20 44D 20 44D O5 O5 O 0 1 N N N 4.015 19.729 16.032 -3.528 -2.967 1.105 O5 44D 21 44D O6 O6 O 0 1 N N N 2.945 18.829 14.098 -1.648 -1.422 0.354 O6 44D 22 44D O7 O7 O 0 1 N N N 2.310 17.067 12.232 -0.087 -0.039 -1.034 O7 44D 23 44D O9 O9 O 0 1 N N N 1.304 14.111 12.787 -1.097 4.662 -1.484 O9 44D 24 44D O11 O11 O 0 1 N N N -0.295 15.563 17.230 -5.526 2.244 -0.937 O11 44D 25 44D O12 O12 O 0 1 N N N 0.934 16.693 19.297 -7.236 0.542 -0.120 O12 44D 26 44D O13 O13 O 0 1 N N N -2.272 14.519 12.446 -2.096 3.037 1.387 O13 44D 27 44D O14 O14 O 0 1 N N N -1.989 11.933 11.558 -0.272 4.401 2.650 O14 44D 28 44D C1B C1* C 0 1 N N R 2.892 17.812 11.218 1.166 -0.135 -0.355 C1B 44D 29 44D C2B C2* C 0 1 N N N 4.363 17.657 10.940 1.821 -1.479 -0.684 C2B 44D 30 44D C3B C3* C 0 1 N N S 4.371 16.239 10.348 3.149 -1.588 0.073 C3B 44D 31 44D C4B C4* C 0 1 N N S 3.671 16.239 8.980 3.998 -0.352 -0.246 C4B 44D 32 44D C5B C5* C 0 1 N N S 2.201 16.557 9.289 3.179 0.907 0.050 C5B 44D 33 44D C6B C6* C 0 1 N N N 1.312 16.508 8.079 2.758 0.905 1.521 C6B 44D 34 44D "O3'" O3* O 0 1 N N N 5.792 15.687 10.184 2.897 -1.649 1.478 "O3'" 44D 35 44D O4B O4* O 0 1 N N N 4.235 17.117 8.029 5.175 -0.358 0.565 O4B 44D 36 44D O5B O5* O 0 1 N N N 2.174 17.824 9.989 2.016 0.931 -0.775 O5B 44D 37 44D "C1'" "C1'" C 0 1 N N S 4.946 17.154 6.882 6.195 0.308 -0.182 "C1'" 44D 38 44D "C2'" "C2'" C 0 1 N N N 4.677 18.447 6.170 7.447 0.452 0.685 "C2'" 44D 39 44D "C3'" "C3'" C 0 1 N N S 5.781 19.412 6.378 7.916 -0.941 1.121 "C3'" 44D 40 44D "C4'" "C4'" C 0 1 N N S 7.267 18.954 6.516 8.084 -1.813 -0.129 "C4'" 44D 41 44D "C5'" "C5'" C 0 1 N N S 7.248 17.672 7.405 6.783 -1.787 -0.934 "C5'" 44D 42 44D "C6'" "C6'" C 0 1 N N N 8.670 17.283 7.783 6.928 -2.684 -2.165 "C6'" 44D 43 44D "O4'" "O4'" O 0 1 N N N 8.209 18.792 5.401 9.154 -1.305 -0.927 "O4'" 44D 44 44D "O5'" "O5'" O 0 1 N N N 6.348 16.754 6.794 6.500 -0.453 -1.350 "O5'" 44D 45 44D "N3'" "N3'" N 0 1 N N N 5.766 20.308 5.212 9.200 -0.831 1.825 "N3'" 44D 46 44D HC1 HC1 H 0 1 N N N 1.870 17.597 20.865 -8.815 -1.442 -0.373 HC1 44D 47 44D HC2 HC2 H 0 1 N N N 3.661 19.170 22.087 -9.388 -3.823 -0.120 HC2 44D 48 44D HC3 HC3 H 0 1 N N N 5.087 20.559 20.628 -7.654 -5.463 0.457 HC3 44D 49 44D HC4 HC4 H 0 1 N N N 4.887 20.489 18.128 -5.322 -4.747 0.787 HC4 44D 50 44D HC7 HC7 H 0 1 N N N 0.732 18.247 12.535 -0.398 1.265 0.534 HC7 44D 51 44D HC81 1HC8 H 0 0 N N N 0.176 16.074 11.227 0.506 2.620 -1.255 HC81 44D 52 44D HC82 2HC8 H 0 0 N N N -0.959 16.658 12.367 -0.768 2.078 -2.378 HC82 44D 53 44D H101 1H10 H 0 0 N N N -0.425 14.335 15.148 -3.569 3.780 -0.714 H101 44D 54 44D H102 2H10 H 0 0 N N N -1.514 15.461 14.511 -3.025 3.123 -2.273 H102 44D 55 44D H141 1H14 H 0 0 N N N -0.344 12.080 12.890 0.765 4.000 0.909 H141 44D 56 44D H142 2H14 H 0 0 N N N 0.040 12.493 11.287 -0.280 5.440 0.864 H142 44D 57 44D HO6 HO6 H 0 1 N N N 2.867 18.780 13.153 -1.389 -1.857 -0.469 HO6 44D 58 44D HO9 HO9 H 0 1 N N N 1.312 13.268 13.226 -1.697 5.340 -1.143 HO9 44D 59 44D H11 H11 H 0 1 N N N -0.919 14.955 16.852 -5.712 2.135 -1.880 H11 44D 60 44D H14 H14 H 0 1 N N N -1.836 11.017 11.359 0.460 4.943 2.976 H14 44D 61 44D H1B H1* H 0 1 N N N 2.808 18.806 11.716 1.002 -0.066 0.720 H1B 44D 62 44D "H2'1" 1H2* H 0 0 N N N 5.043 17.827 11.807 1.160 -2.290 -0.380 "H2'1" 44D 63 44D "H2'2" 2H2* H 0 0 N N N 4.826 18.451 10.309 2.007 -1.541 -1.756 "H2'2" 44D 64 44D H3B H3* H 0 1 N N N 3.826 15.581 11.064 3.677 -2.488 -0.244 H3B 44D 65 44D H4B H4* H 0 1 N N N 3.793 15.249 8.481 4.280 -0.364 -1.298 H4B 44D 66 44D H5B H5* H 0 1 N N N 1.768 15.764 9.942 3.786 1.790 -0.152 H5B 44D 67 44D "H6'1" 1H6* H 0 0 N N N 1.403 15.525 7.561 3.645 0.881 2.153 "H6'1" 44D 68 44D "H6'2" 2H6* H 0 0 N N N 0.245 16.739 8.303 2.184 1.807 1.736 "H6'2" 44D 69 44D "H6'3" 3H6* H 0 0 N N N 1.701 17.177 7.276 2.144 0.027 1.723 "H6'3" 44D 70 44D "H3'O" OH3* H 0 0 N N N 5.797 14.810 9.818 2.351 -2.432 1.630 "H3'O" 44D 71 44D "H1'" "H1'" H 0 1 N N N 4.536 16.250 6.374 5.841 1.296 -0.476 "H1'" 44D 72 44D H2B "1H2'" H 0 1 N N N 3.693 18.880 6.465 8.235 0.939 0.110 H2B 44D 73 44D H2D "2H2'" H 0 1 N N N 4.474 18.284 5.086 7.214 1.050 1.566 H2D 44D 74 44D "H3'" "H3'" H 0 1 N N N 5.546 19.814 7.391 7.173 -1.387 1.782 "H3'" 44D 75 44D "H4'" "H4'" H 0 1 N N N 7.736 19.882 6.920 8.306 -2.838 0.169 "H4'" 44D 76 44D "H5'" "H5'" H 0 1 N N N 6.820 17.780 8.429 5.965 -2.154 -0.313 "H5'" 44D 77 44D H6B "1H6'" H 0 1 N N N 9.218 18.123 8.271 7.745 -2.318 -2.786 H6B 44D 78 44D H6D "2H6'" H 0 1 N N N 8.656 16.367 8.418 7.142 -3.705 -1.848 H6D 44D 79 44D H6E "3H6'" H 0 1 N N N 9.323 17.162 6.887 6.001 -2.668 -2.738 H6E 44D 80 44D "H4'O" "OH4'" H 0 0 N N N 9.113 18.513 5.485 9.225 -1.881 -1.700 "H4'O" 44D 81 44D "H3'1" "1H3'" H 0 0 N N N 4.862 20.753 5.054 9.041 -0.240 2.627 "H3'1" 44D 82 44D "H3'2" "2H3'" H 0 0 N N N 6.526 20.973 5.355 9.415 -1.750 2.181 "H3'2" 44D 83 # # 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 44D C1 C2 DOUB Y N 1 44D C1 C15 SING Y N 2 44D C1 HC1 SING N N 3 44D C2 C3 SING Y N 4 44D C2 HC2 SING N N 5 44D C3 C4 DOUB Y N 6 44D C3 HC3 SING N N 7 44D C4 C16 SING Y N 8 44D C4 HC4 SING N N 9 44D C5 C16 SING N N 10 44D C5 C17 SING N N 11 44D C5 O5 DOUB N N 12 44D C6 C17 DOUB Y N 13 44D C6 C20 SING Y N 14 44D C6 O6 SING N N 15 44D C7 C8 SING N N 16 44D C7 C20 SING N N 17 44D C7 O7 SING N N 18 44D C7 HC7 SING N N 19 44D C8 C9 SING N N 20 44D C8 HC81 SING N N 21 44D C8 HC82 SING N N 22 44D C9 C10 SING N N 23 44D C9 C13 SING N N 24 44D C9 O9 SING N N 25 44D C10 C19 SING N N 26 44D C10 H101 SING N N 27 44D C10 H102 SING N N 28 44D C11 C18 DOUB Y N 29 44D C11 C19 SING Y N 30 44D C11 O11 SING N N 31 44D C12 C15 SING N N 32 44D C12 C18 SING N N 33 44D C12 O12 DOUB N N 34 44D C13 C14 SING N N 35 44D C13 O13 DOUB N N 36 44D C14 O14 SING N N 37 44D C14 H141 SING N N 38 44D C14 H142 SING N N 39 44D C15 C16 DOUB Y N 40 44D C17 C18 SING Y N 41 44D C19 C20 DOUB Y N 42 44D O6 HO6 SING N N 43 44D O7 C1B SING N N 44 44D O9 HO9 SING N N 45 44D O11 H11 SING N N 46 44D O14 H14 SING N N 47 44D C1B C2B SING N N 48 44D C1B O5B SING N N 49 44D C1B H1B SING N N 50 44D C2B C3B SING N N 51 44D C2B "H2'1" SING N N 52 44D C2B "H2'2" SING N N 53 44D C3B C4B SING N N 54 44D C3B "O3'" SING N N 55 44D C3B H3B SING N N 56 44D C4B C5B SING N N 57 44D C4B O4B SING N N 58 44D C4B H4B SING N N 59 44D C5B C6B SING N N 60 44D C5B O5B SING N N 61 44D C5B H5B SING N N 62 44D C6B "H6'1" SING N N 63 44D C6B "H6'2" SING N N 64 44D C6B "H6'3" SING N N 65 44D "O3'" "H3'O" SING N N 66 44D O4B "C1'" SING N N 67 44D "C1'" "C2'" SING N N 68 44D "C1'" "O5'" SING N N 69 44D "C1'" "H1'" SING N N 70 44D "C2'" "C3'" SING N N 71 44D "C2'" H2B SING N N 72 44D "C2'" H2D SING N N 73 44D "C3'" "C4'" SING N N 74 44D "C3'" "N3'" SING N N 75 44D "C3'" "H3'" SING N N 76 44D "C4'" "C5'" SING N N 77 44D "C4'" "O4'" SING N N 78 44D "C4'" "H4'" SING N N 79 44D "C5'" "C6'" SING N N 80 44D "C5'" "O5'" SING N N 81 44D "C5'" "H5'" SING N N 82 44D "C6'" H6B SING N N 83 44D "C6'" H6D SING N N 84 44D "C6'" H6E SING N N 85 44D "O4'" "H4'O" SING N N 86 44D "N3'" "H3'1" SING N N 87 44D "N3'" "H3'2" SING N N 88 # # 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 44D SMILES ACDLabs 10.04 "O=C2c1c(O)c6c(c(O)c1C(=O)c3ccccc23)CC(O)(C(=O)CO)CC6OC5OC(C(OC4OC(C)C(O)C(N)C4)C(O)C5)C" 44D SMILES_CANONICAL CACTVS 3.341 "C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@@H]2[C@H](C)O[C@H](C[C@@H]2O)O[C@H]3C[C@@](O)(Cc4c(O)c5C(=O)c6ccccc6C(=O)c5c(O)c34)C(=O)CO" 44D SMILES CACTVS 3.341 "C[CH]1O[CH](C[CH](N)[CH]1O)O[CH]2[CH](C)O[CH](C[CH]2O)O[CH]3C[C](O)(Cc4c(O)c5C(=O)c6ccccc6C(=O)c5c(O)c34)C(=O)CO" 44D 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]2O)O[C@H]3C[C@@](Cc4c3c(c5c(c4O)C(=O)c6ccccc6C5=O)O)(C(=O)CO)O)C)N)O" 44D SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(CC(O1)OC2C(OC(CC2O)OC3CC(Cc4c3c(c5c(c4O)C(=O)c6ccccc6C5=O)O)(C(=O)CO)O)C)N)O" 44D InChI InChI 1.03 "InChI=1S/C32H37NO13/c1-12-26(37)17(33)7-21(43-12)46-31-13(2)44-22(8-18(31)35)45-19-10-32(42,20(36)11-34)9-16-23(19)30(41)25-24(29(16)40)27(38)14-5-3-4-6-15(14)28(25)39/h3-6,12-13,17-19,21-22,26,31,34-35,37,40-42H,7-11,33H2,1-2H3/t12-,13-,17-,18-,19-,21-,22-,26+,31+,32-/m0/s1" 44D InChIKey InChI 1.03 VQHRZZISQVWPLK-UIRGBLDSSA-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 44D "SYSTEMATIC NAME" ACDLabs 10.04 "(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 4-O-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)-2,6-dideoxy-alpha-L-lyxo-hexopyranoside" 44D "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(7S,9S)-7-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyethanoyl)-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 44D "Create component" 2002-12-16 RCSB 44D "Modify descriptor" 2011-06-04 RCSB 44D "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 44D _pdbx_chem_comp_synonyms.name "4'-(O-ALPHA-L-DAUNOSAMINYL)-4-DEMETHOXYDOXORUBICIN" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##