data_AO5
# 
_chem_comp.id                                    AO5 
_chem_comp.name                                  
;N'-((2S,3R)-3-AMINO-2-HYDROXY-5-(ISOPROPYLSULFANYL)PENTANOYL)-N-3-CHLOROBENZOYL HYDRAZIDE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H22 Cl N3 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-11-10 
_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                        359.871 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AO5 
_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        1R58 
_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 
AO5 C1   C1   C  0 1 N N N 19.571 33.036 16.100 -7.131 1.220  0.967  C1   AO5 1  
AO5 C2   C2   C  0 1 N N N 18.793 34.079 15.297 -6.696 2.585  0.431  C2   AO5 2  
AO5 C3   C3   C  0 1 N N N 19.923 33.593 17.471 -8.657 1.118  0.925  C3   AO5 3  
AO5 S4   S4   S  0 1 N N N 21.051 32.529 15.271 -6.410 -0.091 -0.059 S4   AO5 4  
AO5 C5   C5   C  0 1 N N N 20.810 30.763 15.085 -4.649 0.166  0.293  C5   AO5 5  
AO5 C6   C6   C  0 1 N N N 21.056 29.995 16.375 -3.818 -0.856 -0.486 C6   AO5 6  
AO5 C7   C7   C  0 1 N N R 20.612 28.546 16.217 -2.333 -0.639 -0.188 C7   AO5 7  
AO5 N8   N8   N  0 1 N N N 21.922 27.962 15.874 -2.071 -0.924 1.229  N8   AO5 8  
AO5 C9   C9   C  0 1 N N S 20.022 27.964 17.561 -1.496 -1.577 -1.061 C9   AO5 9  
AO5 O10  O10  O  0 1 N N N 20.038 26.541 17.562 -1.927 -2.925 -0.860 O10  AO5 10 
AO5 C11  C11  C  0 1 N N N 18.592 28.424 17.742 -0.043 -1.452 -0.682 C11  AO5 11 
AO5 O12  O12  O  0 1 N N N 17.639 27.859 17.239 0.540  -2.398 -0.194 O12  AO5 12 
AO5 N13  N13  N  0 1 N N N 18.498 29.657 18.561 0.609  -0.290 -0.884 N13  AO5 13 
AO5 N14  N14  N  0 1 N N N 17.215 30.315 18.820 1.960  -0.174 -0.532 N14  AO5 14 
AO5 C15  C15  C  0 1 N N N 16.560 31.046 17.858 2.611  0.988  -0.734 C15  AO5 15 
AO5 O16  O16  O  0 1 N N N 17.076 31.140 16.725 2.027  1.936  -1.223 O16  AO5 16 
AO5 C17  C17  C  0 1 Y N N 15.250 31.707 18.167 4.037  1.111  -0.362 C17  AO5 17 
AO5 C18  C18  C  0 1 Y N N 14.571 31.731 19.506 4.715  2.313  -0.571 C18  AO5 18 
AO5 C19  C19  C  0 1 Y N N 13.261 32.435 19.649 6.045  2.422  -0.222 C19  AO5 19 
AO5 C20  C20  C  0 1 Y N N 12.626 33.107 18.477 6.708  1.342  0.335  C20  AO5 20 
AO5 C21  C21  C  0 1 Y N N 13.316 33.065 17.175 6.042  0.147  0.544  C21  AO5 21 
AO5 C22  C22  C  0 1 Y N N 14.589 32.390 17.011 4.709  0.027  0.204  C22  AO5 22 
AO5 CL23 CL23 CL 0 0 N N N 12.648 33.809 15.787 6.883  -1.202 1.243  CL23 AO5 23 
AO5 H1   H1   H  0 1 N N N 18.915 32.141 16.208 -6.787 1.107  1.995  H1   AO5 24 
AO5 H21  1H2  H  0 1 N N N 19.342 35.047 15.227 -5.608 2.657  0.461  H21  AO5 25 
AO5 H22A 2H2  H  0 0 N N N 18.535 33.671 14.292 -7.039 2.698  -0.597 H22A AO5 26 
AO5 H23  3H2  H  0 1 N N N 17.892 34.442 15.845 -7.129 3.372  1.047  H23  AO5 27 
AO5 H31  1H3  H  0 1 N N N 19.022 33.956 18.019 -9.001 1.231  -0.103 H31  AO5 28 
AO5 H32  2H3  H  0 1 N N N 20.490 32.832 18.057 -8.967 0.146  1.307  H32  AO5 29 
AO5 H33  3H3  H  0 1 N N N 20.472 34.561 17.401 -9.090 1.906  1.542  H33  AO5 30 
AO5 H51  1H5  H  0 1 N N N 21.436 30.360 14.255 -4.361 1.173  -0.008 H51  AO5 31 
AO5 H52  2H5  H  0 1 N N N 19.798 30.539 14.674 -4.470 0.041  1.361  H52  AO5 32 
AO5 H61  1H6  H  0 1 N N N 20.572 30.486 17.251 -4.106 -1.863 -0.184 H61  AO5 33 
AO5 H62  2H6  H  0 1 N N N 22.117 30.072 16.710 -3.997 -0.731 -1.554 H62  AO5 34 
AO5 H7   H7   H  0 1 N N N 19.794 28.357 15.484 -2.066 0.395  -0.406 H7   AO5 35 
AO5 HN81 1HN8 H  0 0 N N N 22.685 28.137 16.528 -2.715 -0.360 1.762  HN81 AO5 36 
AO5 HN82 2HN8 H  0 0 N N N 21.625 26.992 15.768 -2.331 -1.886 1.384  HN82 AO5 37 
AO5 H9   H9   H  0 1 N N N 20.661 28.337 18.395 -1.623 -1.308 -2.109 H9   AO5 38 
AO5 H10  H10  H  0 1 N N N 19.683 26.191 18.371 -1.798 -3.123 0.078  H10  AO5 39 
AO5 H13  H13  H  0 1 N N N 19.343 30.066 18.959 0.142  0.466  -1.274 H13  AO5 40 
AO5 H14  H14  H  0 1 N N N 16.749 30.261 19.726 2.426  -0.930 -0.142 H14  AO5 41 
AO5 H18  H18  H  0 1 N N N 15.031 31.236 20.378 4.199  3.157  -1.005 H18  AO5 42 
AO5 H19  H19  H  0 1 N N N 12.757 32.459 20.630 6.570  3.352  -0.383 H19  AO5 43 
AO5 H20  H20  H  0 1 N N N 11.659 33.628 18.572 7.750  1.432  0.606  H20  AO5 44 
AO5 H22  H22  H  0 1 N N N 15.053 32.396 16.010 4.190  -0.906 0.368  H22  AO5 45 
# 
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 
AO5 C1  C2   SING N N 1  
AO5 C1  C3   SING N N 2  
AO5 C1  S4   SING N N 3  
AO5 C1  H1   SING N N 4  
AO5 C2  H21  SING N N 5  
AO5 C2  H22A SING N N 6  
AO5 C2  H23  SING N N 7  
AO5 C3  H31  SING N N 8  
AO5 C3  H32  SING N N 9  
AO5 C3  H33  SING N N 10 
AO5 S4  C5   SING N N 11 
AO5 C5  C6   SING N N 12 
AO5 C5  H51  SING N N 13 
AO5 C5  H52  SING N N 14 
AO5 C6  C7   SING N N 15 
AO5 C6  H61  SING N N 16 
AO5 C6  H62  SING N N 17 
AO5 C7  N8   SING N N 18 
AO5 C7  C9   SING N N 19 
AO5 C7  H7   SING N N 20 
AO5 N8  HN81 SING N N 21 
AO5 N8  HN82 SING N N 22 
AO5 C9  O10  SING N N 23 
AO5 C9  C11  SING N N 24 
AO5 C9  H9   SING N N 25 
AO5 O10 H10  SING N N 26 
AO5 C11 O12  DOUB N N 27 
AO5 C11 N13  SING N N 28 
AO5 N13 N14  SING N N 29 
AO5 N13 H13  SING N N 30 
AO5 N14 C15  SING N N 31 
AO5 N14 H14  SING N N 32 
AO5 C15 O16  DOUB N N 33 
AO5 C15 C17  SING N N 34 
AO5 C17 C18  SING Y N 35 
AO5 C17 C22  DOUB Y N 36 
AO5 C18 C19  DOUB Y N 37 
AO5 C18 H18  SING N N 38 
AO5 C19 C20  SING Y N 39 
AO5 C19 H19  SING N N 40 
AO5 C20 C21  DOUB Y N 41 
AO5 C20 H20  SING N N 42 
AO5 C21 C22  SING Y N 43 
AO5 C21 CL23 SING N N 44 
AO5 C22 H22  SING N N 45 
# 
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 
AO5 SMILES           ACDLabs              10.04 O=C(c1cc(Cl)ccc1)NNC(=O)C(O)C(N)CCSC(C)C                                                                                                                            
AO5 InChI            InChI                1.02b InChI=1/C15H22ClN3O3S/c1-9(2)23-7-6-12(17)13(20)15(22)19-18-14(21)10-4-3-5-11(16)8-10/h3-5,8-9,12-13,20H,6-7,17H2,1-2H3,(H,18,21)(H,19,22)/t12-,13+/m1/s1/f/h18-19H 
AO5 InChIKey         InChI                1.02b BYBVYIPUGPZRSX-RVBGABGLDH                                                                                                                                           
AO5 SMILES_CANONICAL CACTVS               3.341 CC(C)SCC[C@@H](N)[C@H](O)C(=O)NNC(=O)c1cccc(Cl)c1                                                                                                                   
AO5 SMILES           CACTVS               3.341 CC(C)SCC[CH](N)[CH](O)C(=O)NNC(=O)c1cccc(Cl)c1                                                                                                                      
AO5 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)SCC[C@H]([C@@H](C(=O)NNC(=O)c1cccc(c1)Cl)O)N                                                                                                                   
AO5 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)SCCC(C(C(=O)NNC(=O)c1cccc(c1)Cl)O)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 
AO5 "SYSTEMATIC NAME" ACDLabs              10.04 3-amino-1-{2-[(3-chlorophenyl)carbonyl]hydrazino}-3,4-dideoxy-5-S-(1-methylethyl)-5-thio-D-threo-pentose 
AO5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "N'-[(2S,3R)-3-amino-2-hydroxy-5-propan-2-ylsulfanyl-pentanoyl]-3-chloro-benzohydrazide"                 
# 
