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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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                1.02b VQHRZZISQVWPLK-UIRGBLDSBQ 
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 
# 
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 
# 
