data_CBN
# 
_chem_comp.id                                    CBN 
_chem_comp.name                                  CLOROBIOCIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C35 H37 Cl N2 O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-02-14 
_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                        697.128 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CBN 
_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        1KZN 
_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 
CBN C7   C7   C  0 1 N N N 18.802 24.105 36.349 2.411  1.282  8.517   C7   CBN 1  
CBN C8   C8   C  0 1 N N N 18.867 28.061 34.496 -0.133 1.983  4.578   C8   CBN 2  
CBN C12  C12  C  0 1 N N N 19.780 26.263 33.194 2.021  3.118  5.125   C12  CBN 3  
CBN C13  C13  C  0 1 N N R 20.083 26.085 35.750 1.173  1.274  6.585   C13  CBN 4  
CBN C21  C21  C  0 1 N N S 20.553 26.864 37.001 0.394  -0.045 6.597   C21  CBN 5  
CBN C22  C22  C  0 1 N N R 21.980 27.398 36.780 1.054  -1.013 5.608   C22  CBN 6  
CBN C23  C23  C  0 1 N N S 21.939 28.269 35.489 1.162  -0.332 4.241   C23  CBN 7  
CBN C24  C24  C  0 1 N N N 20.006 27.028 34.495 1.273  1.784  5.145   C24  CBN 8  
CBN CL1  CL1  CL 0 0 N N N 19.240 31.404 36.920 2.791  -2.924 1.123   CL1  CBN 9  
CBN C27  C27  C  0 1 Y N N 21.080 30.527 34.993 1.573  -0.697 2.072   C27  CBN 10 
CBN C28  C28  C  0 1 Y N N 20.118 31.521 35.418 2.015  -1.381 0.951   C28  CBN 11 
CBN C4   C4   C  0 1 Y N N 19.899 32.669 34.581 1.831  -0.831 -0.310  C4   CBN 12 
CBN C11  C11  C  0 1 Y N N 18.971 34.987 34.335 2.089  -0.976 -2.644  C11  CBN 13 
CBN C31  C31  C  0 1 Y N N 19.654 35.136 33.018 1.474  0.272  -2.854  C31  CBN 14 
CBN C9   C9   C  0 1 Y N N 20.445 34.112 32.549 1.020  0.997  -1.769  C9   CBN 15 
CBN C32  C32  C  0 1 Y N N 20.627 32.839 33.318 1.205  0.421  -0.430  C32  CBN 16 
CBN C33  C33  C  0 1 Y N N 21.574 31.819 32.890 0.770  1.101  0.711   C33  CBN 17 
CBN C35  C35  C  0 1 Y N N 21.807 30.676 33.711 0.954  0.544  1.944   C35  CBN 18 
CBN C14  C14  C  0 1 N N N 18.084 36.676 31.852 0.648  0.064  -5.081  C14  CBN 19 
CBN C15  C15  C  0 1 Y N N 17.000 35.742 31.497 0.584  0.540  -6.476  C15  CBN 20 
CBN C16  C16  C  0 1 Y N N 17.292 34.507 30.756 -0.108 -0.199 -7.437  C16  CBN 21 
CBN C17  C17  C  0 1 Y N N 16.212 33.701 30.252 -0.170 0.250  -8.738  C17  CBN 22 
CBN C18  C18  C  0 1 Y N N 14.845 34.145 30.489 0.465  1.433  -9.096  C18  CBN 23 
CBN C19  C19  C  0 1 Y N N 14.544 35.351 31.245 1.160  2.169  -8.144  C19  CBN 24 
CBN C20  C20  C  0 1 Y N N 15.620 36.140 31.766 1.222  1.729  -6.841  C20  CBN 25 
CBN C25  C25  C  0 1 N N N 16.501 32.412 29.517 -0.922 -0.543 -9.774  C25  CBN 26 
CBN C26  C26  C  0 1 N N N 16.296 31.130 30.375 -2.356 -0.081 -9.818  C26  CBN 27 
CBN C29  C29  C  0 1 N N N 17.196 30.279 30.898 -3.322 -0.911 -9.510  C29  CBN 28 
CBN C30  C30  C  0 1 N N N 16.721 29.156 31.716 -4.758 -0.501 -9.707  C30  CBN 29 
CBN C34  C34  C  0 1 N N N 18.621 30.536 30.738 -2.996 -2.274 -8.958  C34  CBN 30 
CBN N1   N1   N  0 1 N N N 19.318 36.294 32.184 1.322  0.777  -4.156  N1   CBN 31 
CBN O1   O1   O  0 1 N N N 18.830 25.504 36.088 2.486  1.060  7.107   O1   CBN 32 
CBN O2   O2   O  0 1 N N N 20.518 26.019 38.154 -0.981 0.197  6.202   O2   CBN 33 
CBN O3   O3   O  0 1 N N N 21.262 27.686 34.374 1.977  0.833  4.345   O3   CBN 34 
CBN O4   O4   O  0 1 N N N 21.276 29.461 35.867 1.749  -1.238 3.305   O4   CBN 35 
CBN O5   O5   O  0 1 N N N 21.115 34.220 31.371 0.423  2.201  -1.934  O5   CBN 36 
CBN O6   O6   O  0 1 Y N N 19.061 33.742 35.021 2.250  -1.486 -1.413  O6   CBN 37 
CBN O7   O7   O  0 1 N N N 18.192 35.797 34.737 2.487  -1.610 -3.606  O7   CBN 38 
CBN O8   O8   O  0 1 N N N 17.887 37.824 31.757 0.092  -0.969 -4.765  O8   CBN 39 
CBN O9   O9   O  0 1 N N N 13.797 33.380 30.044 0.407  1.870  -10.380 O9   CBN 40 
CBN C1   C1   C  0 1 Y N N 19.513 23.742 41.559 -5.575 -0.481 6.074   C1   CBN 41 
CBN C2   C2   C  0 1 Y N N 19.556 24.269 40.345 -4.462 -1.059 6.692   C2   CBN 42 
CBN C3   C3   C  0 1 Y N N 20.040 25.633 40.453 -3.357 -0.339 6.285   C3   CBN 43 
CBN N2   N2   N  0 1 Y N N 20.310 25.940 41.856 -3.797 0.646  5.431   N2   CBN 44 
CBN C5   C5   C  0 1 Y N N 19.890 24.725 42.561 -5.138 0.550  5.312   C5   CBN 45 
CBN C6   C6   C  0 1 N N N 19.681 24.860 44.006 -6.009 1.445  4.469   C6   CBN 46 
CBN C10  C10  C  0 1 N N N 20.378 26.573 39.407 -1.969 -0.584 6.683   C10  CBN 47 
CBN O10  O10  O  0 1 N N N 20.524 27.762 39.612 -1.707 -1.493 7.449   O10  CBN 48 
CBN O11  O11  O  0 1 N N N 22.853 26.265 36.710 0.260  -2.195 5.494   O11  CBN 49 
CBN H71  1H7  H  0 1 N N N 17.819 23.649 36.614 3.394  1.129  8.962   H71  CBN 50 
CBN H72  2H7  H  0 1 N N N 19.238 23.559 35.480 2.081  2.304  8.706   H72  CBN 51 
CBN H73  3H7  H  0 1 N N N 19.546 23.863 37.143 1.700  0.584  8.958   H73  CBN 52 
CBN H81  1H8  H  0 1 N N N 19.032 28.619 35.446 -0.651 1.024  4.544   H81  CBN 53 
CBN H82  2H8  H  0 1 N N N 18.819 28.700 33.583 -0.688 2.672  5.214   H82  CBN 54 
CBN H83  3H8  H  0 1 N N N 17.846 27.626 34.384 -0.064 2.394  3.571   H83  CBN 55 
CBN H121 1H12 H  0 0 N N N 20.605 25.513 33.193 2.087  3.483  4.100   H121 CBN 56 
CBN H122 2H12 H  0 0 N N N 18.759 25.828 33.082 1.484  3.845  5.736   H122 CBN 57 
CBN H123 3H12 H  0 0 N N N 19.732 26.902 32.281 3.024  2.978  5.526   H123 CBN 58 
CBN H13  H13  H  0 1 N N N 20.804 25.284 35.464 0.653  2.011  7.197   H13  CBN 59 
CBN H21  H21  H  0 1 N N N 19.864 27.724 37.169 0.417  -0.474 7.599   H21  CBN 60 
CBN H22  H22  H  0 1 N N N 22.364 28.046 37.601 2.050  -1.275 5.964   H22  CBN 61 
CBN H23  H23  H  0 1 N N N 22.984 28.411 35.129 0.167  -0.050 3.897   H23  CBN 62 
CBN H33  H33  H  0 1 N N N 22.119 31.913 31.935 0.290  2.063  0.618   H33  CBN 63 
CBN H35  H35  H  0 1 N N N 22.533 29.923 33.361 0.617  1.069  2.826   H35  CBN 64 
CBN H16  H16  H  0 1 N N N 18.330 34.182 30.576 -0.602 -1.118 -7.159  H16  CBN 65 
CBN H19  H19  H  0 1 N N N 13.502 35.666 31.422 1.653  3.088  -8.427  H19  CBN 66 
CBN H20  H20  H  0 1 N N N 15.390 37.038 32.363 1.762  2.301  -6.102  H20  CBN 67 
CBN H251 1H25 H  0 0 N N N 15.900 32.354 28.579 -0.462 -0.394 -10.751 H251 CBN 68 
CBN H252 2H25 H  0 0 N N N 17.528 32.431 29.083 -0.890 -1.601 -9.515  H252 CBN 69 
CBN H26  H26  H  0 1 N N N 15.307 30.744 30.674 -2.587 0.934  -10.104 H26  CBN 70 
CBN H301 1H30 H  0 0 N N N 17.467 28.450 32.149 -5.414 -1.316 -9.398  H301 CBN 71 
CBN H302 2H30 H  0 0 N N N 16.083 29.555 32.539 -4.970 0.383  -9.107  H302 CBN 72 
CBN H303 3H30 H  0 0 N N N 15.975 28.572 31.127 -4.931 -0.276 -10.760 H303 CBN 73 
CBN H341 1H34 H  0 0 N N N 19.367 29.830 31.171 -1.921 -2.352 -8.793  H341 CBN 74 
CBN H342 2H34 H  0 0 N N N 18.837 30.654 29.650 -3.519 -2.418 -8.012  H342 CBN 75 
CBN H343 3H34 H  0 0 N N N 18.839 31.559 31.121 -3.311 -3.039 -9.668  H343 CBN 76 
CBN HN1  HN1  H  0 1 N N N 20.028 36.908 31.786 1.702  1.638  -4.390  HN1  CBN 77 
CBN H5   H5   H  0 1 N N N 21.661 33.513 31.047 0.335  2.341  -2.887  H5   CBN 78 
CBN H9   H9   H  0 1 N N N 12.905 33.669 30.198 1.165  1.486  -10.841 H9   CBN 79 
CBN H1   H1   H  0 1 N N N 19.220 22.688 41.706 -6.600 -0.803 6.182   H1   CBN 80 
CBN H2   H2   H  0 1 N N N 19.256 23.701 39.448 -4.466 -1.904 7.364   H2   CBN 81 
CBN HN2  HN2  H  0 1 N N N 20.698 26.797 42.249 -3.236 1.302  4.988   HN2  CBN 82 
CBN H61  1H6  H  0 1 N N N 19.970 25.614 44.774 -5.557 2.435  4.404   H61  CBN 83 
CBN H62  2H6  H  0 1 N N N 18.574 24.786 44.117 -6.102 1.022  3.468   H62  CBN 84 
CBN H63  3H6  H  0 1 N N N 20.078 23.903 44.417 -6.996 1.524  4.923   H63  CBN 85 
CBN H11  H11  H  0 1 N N N 23.733 26.594 36.573 0.710  -2.774 4.864   H11  CBN 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 
CBN C7  O1   SING N N 1  
CBN C7  H71  SING N N 2  
CBN C7  H72  SING N N 3  
CBN C7  H73  SING N N 4  
CBN C8  C24  SING N N 5  
CBN C8  H81  SING N N 6  
CBN C8  H82  SING N N 7  
CBN C8  H83  SING N N 8  
CBN C12 C24  SING N N 9  
CBN C12 H121 SING N N 10 
CBN C12 H122 SING N N 11 
CBN C12 H123 SING N N 12 
CBN C13 C21  SING N N 13 
CBN C13 C24  SING N N 14 
CBN C13 O1   SING N N 15 
CBN C13 H13  SING N N 16 
CBN C21 C22  SING N N 17 
CBN C21 O2   SING N N 18 
CBN C21 H21  SING N N 19 
CBN C22 C23  SING N N 20 
CBN C22 O11  SING N N 21 
CBN C22 H22  SING N N 22 
CBN C23 O3   SING N N 23 
CBN C23 O4   SING N N 24 
CBN C23 H23  SING N N 25 
CBN C24 O3   SING N N 26 
CBN CL1 C28  SING N N 27 
CBN C27 C28  DOUB Y N 28 
CBN C27 C35  SING Y N 29 
CBN C27 O4   SING N N 30 
CBN C28 C4   SING Y N 31 
CBN C4  C32  DOUB Y N 32 
CBN C4  O6   SING Y N 33 
CBN C11 C31  SING Y N 34 
CBN C11 O6   SING Y N 35 
CBN C11 O7   DOUB N N 36 
CBN C31 C9   DOUB Y N 37 
CBN C31 N1   SING N N 38 
CBN C9  C32  SING Y N 39 
CBN C9  O5   SING N N 40 
CBN C32 C33  SING Y N 41 
CBN C33 C35  DOUB Y N 42 
CBN C33 H33  SING N N 43 
CBN C35 H35  SING N N 44 
CBN C14 C15  SING N N 45 
CBN C14 N1   SING N N 46 
CBN C14 O8   DOUB N N 47 
CBN C15 C16  DOUB Y N 48 
CBN C15 C20  SING Y N 49 
CBN C16 C17  SING Y N 50 
CBN C16 H16  SING N N 51 
CBN C17 C18  DOUB Y N 52 
CBN C17 C25  SING N N 53 
CBN C18 C19  SING Y N 54 
CBN C18 O9   SING N N 55 
CBN C19 C20  DOUB Y N 56 
CBN C19 H19  SING N N 57 
CBN C20 H20  SING N N 58 
CBN C25 C26  SING N N 59 
CBN C25 H251 SING N N 60 
CBN C25 H252 SING N N 61 
CBN C26 C29  DOUB N N 62 
CBN C26 H26  SING N N 63 
CBN C29 C30  SING N N 64 
CBN C29 C34  SING N N 65 
CBN C30 H301 SING N N 66 
CBN C30 H302 SING N N 67 
CBN C30 H303 SING N N 68 
CBN C34 H341 SING N N 69 
CBN C34 H342 SING N N 70 
CBN C34 H343 SING N N 71 
CBN N1  HN1  SING N N 72 
CBN O2  C10  SING N N 73 
CBN O5  H5   SING N N 74 
CBN O9  H9   SING N N 75 
CBN C1  C2   SING Y N 76 
CBN C1  C5   DOUB Y N 77 
CBN C1  H1   SING N N 78 
CBN C2  C3   DOUB Y N 79 
CBN C2  H2   SING N N 80 
CBN C3  N2   SING Y N 81 
CBN C3  C10  SING N N 82 
CBN N2  C5   SING Y N 83 
CBN N2  HN2  SING N N 84 
CBN C5  C6   SING N N 85 
CBN C6  H61  SING N N 86 
CBN C6  H62  SING N N 87 
CBN C6  H63  SING N N 88 
CBN C10 O10  DOUB N N 89 
CBN O11 H11  SING N N 90 
# 
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 
CBN SMILES           ACDLabs              10.04 O=C(c1ccc(O)c(c1)C\C=C(/C)C)NC4=C(O)c5ccc(OC3OC(C(OC)C(OC(=O)c2ccc(n2)C)C3O)(C)C)c(Cl)c5OC4=O 
CBN InChI            InChI                1.02b 
;InChI=1/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1/f/h38H
;
CBN InChIKey         InChI                1.02b FJAQNRBDVKIIKK-HZAHFXSADU 
CBN SMILES_CANONICAL CACTVS               3.341 CO[C@@H]1[C@@H](OC(=O)c2[nH]c(C)cc2)[C@@H](O)[C@H](Oc3ccc4C(=C(NC(=O)c5ccc(O)c(CC=C(C)C)c5)C(=O)Oc4c3Cl)O)OC1(C)C 
CBN SMILES           CACTVS               3.341 CO[CH]1[CH](OC(=O)c2[nH]c(C)cc2)[CH](O)[CH](Oc3ccc4C(=C(NC(=O)c5ccc(O)c(CC=C(C)C)c5)C(=O)Oc4c3Cl)O)OC1(C)C 
CBN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1ccc([nH]1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)Oc3ccc4c(c3Cl)OC(=O)C(=C4O)NC(=O)c5ccc(c(c5)CC=C(C)C)O)O 
CBN SMILES           "OpenEye OEToolkits" 1.5.0 Cc1ccc([nH]1)C(=O)OC2C(C(OC(C2OC)(C)C)Oc3ccc4c(c3Cl)OC(=O)C(=C4O)NC(=O)c5ccc(c(c5)CC=C(C)C)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 
CBN "SYSTEMATIC NAME" ACDLabs              10.04 N-[8-chloro-7-({6-deoxy-5-methyl-4-O-methyl-3-O-[(5-methyl-1H-pyrrol-2-yl)carbonyl]-beta-D-gulopyranosyl}oxy)-4-hydroxy-2-oxo-2H-chromen-3-yl]-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide           
CBN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]carbonylamino]-2-oxo-chromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyl-oxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate" 
# 
