data_MA8
# 
_chem_comp.id                                    MA8 
_chem_comp.name                                  "(2S,3R,5S,6S)-2,3,4,5,6-PENTAHYDROXYCYCLOHEXYL 2-(L-CYSTEINYLAMINO)-2-DEOXY-ALPHA-L-GLUCOPYRANOSIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H28 N2 O11 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-26 
_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                        444.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MA8 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2C27 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
MA8 O1   O1   O 0 1 N N N 4.148 5.088  16.141 -0.556 -1.799 -1.384 O1   MA8 1  
MA8 C1   C1   C 0 1 N N R 4.467 4.346  17.367 -0.805 -0.392 -1.420 C1   MA8 2  
MA8 C2   C2   C 0 1 N N S 3.067 6.966  17.385 1.652  -1.515 -0.381 C2   MA8 3  
MA8 C3   C3   C 0 1 N N R 3.008 5.973  16.203 0.829  -2.136 -1.516 C3   MA8 4  
MA8 O2   O2   O 0 1 N N N 1.787 7.660  17.484 3.044  -1.726 -0.607 O2   MA8 5  
MA8 O3   O3   O 0 1 N N N 3.434 7.041  19.751 1.997  0.472  0.933  O3   MA8 6  
MA8 O4   O4   O 0 1 N N N 3.384 3.408  17.643 -0.408 0.188  -2.661 O4   MA8 7  
MA8 N1   N1   N 0 1 N N N 4.937 4.591  19.755 -0.339 1.719  -0.254 N1   MA8 8  
MA8 C4   C4   C 0 1 N N N 2.916 6.688  14.869 0.919  -3.660 -1.521 C4   MA8 9  
MA8 C5   C5   C 0 1 N N R 4.593 5.325  18.485 -0.089 0.296  -0.254 C5   MA8 10 
MA8 C6   C6   C 0 1 N N R 3.289 6.146  18.652 1.412  -0.006 -0.280 C6   MA8 11 
MA8 O5   O5   O 0 1 N N N 2.743 5.729  13.859 0.127  -4.153 -2.586 O5   MA8 12 
MA8 C7   C7   C 0 1 N N R 2.533 1.142  14.781 -1.533 2.627  -3.958 C7   MA8 13 
MA8 C8   C8   C 0 1 N N N 2.262 -0.153 15.598 -0.932 2.483  -5.361 C8   MA8 14 
MA8 C9   C9   C 0 1 N N N 3.417 2.268  16.815 -1.458 0.119  -3.627 C9   MA8 15 
MA8 C10  C10  C 0 1 N N R 2.415 2.404  15.659 -2.322 1.380  -3.517 C10  MA8 16 
MA8 O6   O6   O 0 1 N N N 4.082 0.896  18.697 0.027  -1.163 -5.018 O6   MA8 17 
MA8 O7   O7   O 0 1 N N N 2.892 -1.412 17.570 0.410  1.089  -6.784 O7   MA8 18 
MA8 O8   O8   O 0 1 N N N 1.065 2.537  16.256 -3.486 1.204  -4.319 O8   MA8 19 
MA8 O9   O9   O 0 1 N N N 2.482 -1.266 14.779 -1.976 2.388  -6.334 O9   MA8 20 
MA8 C11  C11  C 0 1 N N S 3.210 -0.252 16.810 -0.059 1.226  -5.443 C11  MA8 21 
MA8 C12  C12  C 0 1 N N R 3.092 0.995  17.665 -0.841 -0.030 -5.029 C12  MA8 22 
MA8 O10  O10  O 0 1 N N N 1.632 1.228  13.666 -2.372 3.778  -3.921 O10  MA8 23 
MA8 C13  C13  C 0 1 N N N 5.936 5.042  20.561 -1.428 2.288  0.392  C13  MA8 24 
MA8 O11  O11  O 0 1 N N N 6.783 5.786  20.102 -2.278 1.659  1.019  O11  MA8 25 
MA8 C14  C14  C 0 1 N N R 6.103 4.390  21.947 -1.445 3.810  0.262  C14  MA8 26 
MA8 N2   N2   N 0 1 N N N 7.168 3.402  21.861 -2.602 4.200  -0.503 N2   MA8 27 
MA8 C15  C15  C 0 1 N N N 6.552 5.446  22.984 -1.366 4.534  1.608  C15  MA8 28 
MA8 S1   S1   S 0 1 N N N 8.277 6.083  22.500 0.130  4.136  2.570  S1   MA8 29 
MA8 H1   H1   H 0 1 N N N 5.426 3.792  17.237 -1.887 -0.248 -1.333 H1   MA8 30 
MA8 H2   H2   H 0 1 N N N 3.897 7.696  17.241 1.402  -1.989 0.576  H2   MA8 31 
MA8 H3   H3   H 0 1 N N N 2.092 5.348  16.323 1.198  -1.791 -2.489 H3   MA8 32 
MA8 HA   HA   H 0 1 N N N 1.823 8.271  18.211 3.514  -1.121 -0.012 HA   MA8 33 
MA8 HB   HB   H 0 1 N N N 2.635 7.544  19.853 1.620  -0.064 1.646  HB   MA8 34 
MA8 HC   HC   H 0 1 N N N 4.418 3.751  20.012 0.292  2.311  -0.786 HC   MA8 35 
MA8 H4C1 1H4C H 0 0 N N N 3.789 7.355  14.680 0.544  -4.057 -0.578 H4C1 MA8 36 
MA8 H4C2 2H4C H 0 0 N N N 2.121 7.470  14.857 1.954  -3.970 -1.667 H4C2 MA8 37 
MA8 H5   H5   H 0 1 N N N 5.425 6.028  18.247 -0.502 -0.077 0.692  H5   MA8 38 
MA8 H6   H6   H 0 1 N N N 2.424 5.463  18.824 1.912  0.522  -1.101 H6   MA8 39 
MA8 HD   HD   H 0 1 N N N 2.685 6.177  13.023 -0.583 -4.688 -2.190 HD   MA8 40 
MA8 H7   H7   H 0 1 N N N 3.574 1.091  14.384 -0.719 2.805  -3.244 H7   MA8 41 
MA8 H8   H8   H 0 1 N N N 1.205 -0.155 15.952 -0.354 3.375  -5.628 H8   MA8 42 
MA8 H9   H9   H 0 1 N N N 4.443 2.163  16.390 -2.047 -0.776 -3.398 H9   MA8 43 
MA8 H10  H10  H 0 1 N N N 2.654 3.310  15.055 -2.663 1.524  -2.485 H10  MA8 44 
MA8 HH   HH   H 0 1 N N N 3.885 0.123  19.213 -0.188 -1.676 -5.811 HH   MA8 45 
MA8 HI   HI   H 0 1 N N N 3.476 -1.473 18.317 1.076  0.387  -6.768 HI   MA8 46 
MA8 HG   HG   H 0 1 N N N 0.445 2.621  15.541 -3.543 0.256  -4.508 HG   MA8 47 
MA8 HF   HF   H 0 1 N N N 2.316 -2.057 15.278 -1.588 2.670  -7.175 HF   MA8 48 
MA8 H11  H11  H 0 1 N N N 4.259 -0.339 16.441 0.830  1.340  -4.813 H11  MA8 49 
MA8 H12  H12  H 0 1 N N N 2.072 1.071  18.108 -1.621 -0.246 -5.767 H12  MA8 50 
MA8 HE   HE   H 0 1 N N N 1.798 2.019  13.167 -3.128 3.584  -4.496 HE   MA8 51 
MA8 H14  H14  H 0 1 N N N 5.150 3.909  22.269 -0.579 4.101  -0.345 H14  MA8 52 
MA8 H2N1 1H2N H 0 0 N N N 7.243 2.634  22.528 -3.042 5.084  -0.308 H2N1 MA8 53 
MA8 H2N2 2H2N H 0 0 N N N 8.137 3.636  22.079 -3.069 3.510  -1.067 H2N2 MA8 54 
MA8 H151 1H15 H 0 0 N N N 6.518 5.058  24.029 -1.382 5.619  1.462  H151 MA8 55 
MA8 H152 2H15 H 0 0 N N N 5.811 6.271  23.101 -2.232 4.271  2.225  H152 MA8 56 
MA8 HS1  HS1  H 0 1 N N N 8.340 6.228  21.210 -0.521 3.689  3.652  HS1  MA8 57 
# 
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 
MA8 O1  C1   SING N N 1  
MA8 O1  C3   SING N N 2  
MA8 C1  O4   SING N N 3  
MA8 C1  C5   SING N N 4  
MA8 C1  H1   SING N N 5  
MA8 C2  C3   SING N N 6  
MA8 C2  O2   SING N N 7  
MA8 C2  C6   SING N N 8  
MA8 C2  H2   SING N N 9  
MA8 C3  C4   SING N N 10 
MA8 C3  H3   SING N N 11 
MA8 O2  HA   SING N N 12 
MA8 O3  C6   SING N N 13 
MA8 O3  HB   SING N N 14 
MA8 O4  C9   SING N N 15 
MA8 N1  C5   SING N N 16 
MA8 N1  C13  SING N N 17 
MA8 N1  HC   SING N N 18 
MA8 C4  O5   SING N N 19 
MA8 C4  H4C1 SING N N 20 
MA8 C4  H4C2 SING N N 21 
MA8 C5  C6   SING N N 22 
MA8 C5  H5   SING N N 23 
MA8 C6  H6   SING N N 24 
MA8 O5  HD   SING N N 25 
MA8 C7  C8   SING N N 26 
MA8 C7  C10  SING N N 27 
MA8 C7  O10  SING N N 28 
MA8 C7  H7   SING N N 29 
MA8 C8  O9   SING N N 30 
MA8 C8  C11  SING N N 31 
MA8 C8  H8   SING N N 32 
MA8 C9  C10  SING N N 33 
MA8 C9  C12  SING N N 34 
MA8 C9  H9   SING N N 35 
MA8 C10 O8   SING N N 36 
MA8 C10 H10  SING N N 37 
MA8 O6  C12  SING N N 38 
MA8 O6  HH   SING N N 39 
MA8 O7  C11  SING N N 40 
MA8 O7  HI   SING N N 41 
MA8 O8  HG   SING N N 42 
MA8 O9  HF   SING N N 43 
MA8 C11 C12  SING N N 44 
MA8 C11 H11  SING N N 45 
MA8 C12 H12  SING N N 46 
MA8 O10 HE   SING N N 47 
MA8 C13 O11  DOUB N N 48 
MA8 C13 C14  SING N N 49 
MA8 C14 N2   SING N N 50 
MA8 C14 C15  SING N N 51 
MA8 C14 H14  SING N N 52 
MA8 N2  H2N1 SING N N 53 
MA8 N2  H2N2 SING N N 54 
MA8 C15 S1   SING N N 55 
MA8 C15 H151 SING N N 56 
MA8 C15 H152 SING N N 57 
MA8 HS1 S1   SING N N 58 
# 
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 
MA8 SMILES           ACDLabs              10.04 O=C(NC2C(O)C(O)C(OC2OC1C(O)C(O)C(O)C(O)C1O)CO)C(N)CS                                                                                                                                                  
MA8 InChI            InChI                1.02b InChI=1/C15H28N2O11S/c16-3(2-29)14(26)17-5-7(20)6(19)4(1-18)27-15(5)28-13-11(24)9(22)8(21)10(23)12(13)25/h3-13,15,18-25,29H,1-2,16H2,(H,17,26)/t3-,4+,5+,6+,7+,8-,9-,10+,11+,12+,13-,15+/m0/s1/f/h17H 
MA8 InChIKey         InChI                1.02b ZGXSCMBZZVXWGF-FOTNJYHQDB                                                                                                                                                                             
MA8 SMILES_CANONICAL CACTVS               3.341 N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]2O                                                                                           
MA8 SMILES           CACTVS               3.341 N[CH](CS)C(=O)N[CH]1[CH](O)[CH](O)[CH](CO)O[CH]1O[CH]2[CH](O)[CH](O)[CH](O)[CH](O)[CH]2O                                                                                                              
MA8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2[C@@H]([C@@H](C([C@@H]([C@H]2O)O)O)O)O)NC(=O)[C@H](CS)N)O)O)O                                                                                                 
MA8 SMILES           "OpenEye OEToolkits" 1.5.0 C(C1C(C(C(C(O1)OC2C(C(C(C(C2O)O)O)O)O)NC(=O)C(CS)N)O)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 
MA8 "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 2-(L-cysteinylamino)-2-deoxy-alpha-D-glucopyranoside"                                              
MA8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-2-amino-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy-oxan-3-yl]-3-sulfanyl-propanamide 
# 
