data_KSG
# 
_chem_comp.id                                    KSG 
_chem_comp.name                                  "(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-PENTAHYDROXYCYCLOHEXYL 2-AMINO-4-{[CARBOXY(IMINO)METHYL]AMINO}-2,3,4,6-TETRADEOXY-ALPHA-D-ARABINO-HEXOPYRANOSIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C14 H25 N3 O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         KASUGAMYCIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-08-02 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        379.363 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     KSG 
_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        2HHH 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
KSG C1   C1   C 0 1 N N R 305.130 185.050 -6.349 -4.073  2.049  0.258  C1   KSG 1  
KSG O1   O1   O 0 1 N N N 304.020 184.624 -5.555 -4.495  0.734  -0.102 O1   KSG 2  
KSG C2   C2   C 0 1 N N N 302.915 184.459 -6.445 -3.580  0.126  -1.018 C2   KSG 3  
KSG C3   C3   C 0 1 N N S 301.610 184.743 -5.696 -4.384  -0.819 -1.916 C3   KSG 4  
KSG O2   O2   O 0 1 N N N 301.628 186.083 -5.201 -5.279  -0.062 -2.730 O2   KSG 5  
KSG C4   C4   C 0 1 N N S 300.427 184.567 -6.650 -3.476  -1.644 -2.826 C4   KSG 6  
KSG O3   O3   O 0 1 N N N 300.556 185.478 -7.743 -2.766  -0.756 -3.695 O3   KSG 7  
KSG C5   C5   C 0 1 N N N 300.408 183.132 -7.180 -2.479  -2.447 -1.989 C5   KSG 8  
KSG O4   O4   O 0 1 N N N 300.279 182.222 -6.087 -1.634  -3.174 -2.879 O4   KSG 9  
KSG C6   C6   C 0 1 N N S 301.712 182.848 -7.928 -1.634  -1.535 -1.094 C6   KSG 10 
KSG O5   O5   O 0 1 N N N 301.695 181.509 -8.424 -0.845  -2.344 -0.216 O5   KSG 11 
KSG C7   C7   C 0 1 N N R 302.897 183.025 -6.976 -2.503  -0.622 -0.223 C7   KSG 12 
KSG O6   O6   O 0 1 N N N 304.114 182.760 -7.674 -1.639  0.333  0.400  O6   KSG 13 
KSG O7   O7   O 0 1 N N N 304.808 186.281 -6.994 -4.543  3.036  -0.663 O7   KSG 14 
KSG C8   C8   C 0 1 N N R 304.355 187.187 -5.990 -5.969  3.162  -0.713 C8   KSG 15 
KSG C9   C9   C 0 1 N N N 303.819 188.456 -6.654 -6.278  4.214  -1.776 C9   KSG 16 
KSG C10  C10  C 0 1 N N S 305.515 187.554 -5.061 -6.527  3.554  0.662  C10  KSG 17 
KSG C11  C11  C 0 1 N N N 306.025 186.281 -4.374 -6.053  2.568  1.734  C11  KSG 18 
KSG C12  C12  C 0 1 N N S 306.355 185.242 -5.451 -4.536  2.352  1.689  C12  KSG 19 
KSG N1   N1   N 0 1 N N N 307.490 185.710 -6.257 -3.819  3.526  2.195  N1   KSG 20 
KSG N2   N2   N 0 1 N N N 305.052 188.507 -4.051 -7.975  3.565  0.635  N2   KSG 21 
KSG C13  C13  C 0 1 N N N 305.126 189.861 -4.296 -8.749  4.384  1.416  C13  KSG 22 
KSG N3   N3   N 0 1 N N N 305.605 190.292 -5.422 -8.351  5.255  2.288  N3   KSG 23 
KSG C14  C14  C 0 1 N N N 304.655 190.829 -3.269 -10.236 4.250  1.244  C14  KSG 24 
KSG O8   O8   O 0 1 N N N 304.728 192.152 -3.508 -10.899 3.472  1.897  O8   KSG 25 
KSG O9   O9   O 0 1 N N N 304.207 190.427 -2.215 -10.646 5.100  0.293  O9   KSG 26 
KSG H1   H1   H 0 1 N N N 305.353 184.288 -7.110 -2.980  2.047  0.203  H1   KSG 27 
KSG H2   H2   H 0 1 N N N 303.015 185.160 -7.287 -3.142  0.947  -1.597 H2   KSG 28 
KSG H3   H3   H 0 1 N N N 301.509 184.042 -4.854 -5.005  -1.481 -1.301 H3   KSG 29 
KSG HO2  HO2  H 0 1 N N N 301.632 186.070 -4.251 -6.173  -0.364 -2.509 HO2  KSG 30 
KSG H4   H4   H 0 1 N N N 299.489 184.771 -6.112 -4.063  -2.302 -3.476 H4   KSG 31 
KSG HO3  HO3  H 0 1 N N N 300.585 186.368 -7.412 -1.943  -0.531 -3.238 HO3  KSG 32 
KSG H5   H5   H 0 1 N N N 299.557 183.005 -7.865 -3.006  -3.189 -1.378 H5   KSG 33 
KSG HO4  HO4  H 0 1 N N N 300.250 181.332 -6.417 -2.219  -3.703 -3.443 HO4  KSG 34 
KSG H6   H6   H 0 1 N N N 301.811 183.549 -8.770 -0.920  -0.952 -1.688 H6   KSG 35 
KSG HO5  HO5  H 0 1 N N N 301.691 181.523 -9.374 -0.093  -2.658 -0.740 HO5  KSG 36 
KSG H7   H7   H 0 1 N N N 302.798 182.324 -6.134 -2.960  -1.192 0.596  H7   KSG 37 
KSG HO6  HO6  H 0 1 N N N 303.939 182.701 -8.606 -1.347  -0.068 1.232  HO6  KSG 38 
KSG H8   H8   H 0 1 N N N 303.556 186.708 -5.405 -6.398  2.210  -1.052 H8   KSG 39 
KSG H91  1H9  H 0 1 N N N 303.690 189.241 -5.895 -7.176  4.778  -1.510 H91  KSG 40 
KSG H92  2H9  H 0 1 N N N 304.532 188.799 -7.419 -5.446  4.917  -1.874 H92  KSG 41 
KSG H93  3H9  H 0 1 N N N 302.849 188.241 -7.126 -6.444  3.740  -2.749 H93  KSG 42 
KSG H10  H10  H 0 1 N N N 306.328 188.013 -5.643 -6.173  4.558  0.926  H10  KSG 43 
KSG H111 1H11 H 0 0 N N N 305.250 185.886 -3.701 -6.364  2.913  2.728  H111 KSG 44 
KSG H112 2H11 H 0 0 N N N 306.925 186.508 -3.784 -6.551  1.599  1.586  H112 KSG 45 
KSG H12  H12  H 0 1 N N N 306.621 184.286 -4.976 -4.290  1.506  2.341  H12  KSG 46 
KSG HN11 1HN1 H 0 0 N N N 307.202 185.816 -7.209 -4.033  4.409  1.791  HN11 KSG 47 
KSG HN12 2HN1 H 0 0 N N N 307.808 186.590 -5.905 -3.018  3.371  2.763  HN12 KSG 48 
KSG HN2  HN2  H 0 1 N N N 304.682 188.175 -3.183 -8.417  2.919  -0.010 HN2  KSG 49 
KSG HN3  HN3  H 0 1 N N N 305.876 189.525 -6.003 -7.327  5.279  2.339  HN3  KSG 50 
KSG HO9  HO9  H 0 1 N N N 303.955 191.167 -1.675 -11.614 5.050  0.142  HO9  KSG 51 
# 
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 
KSG C1  O7   SING N N 1  
KSG C1  O1   SING N N 2  
KSG C1  C12  SING N N 3  
KSG C1  H1   SING N N 4  
KSG O1  C2   SING N N 5  
KSG C2  C7   SING N N 6  
KSG C2  C3   SING N N 7  
KSG C2  H2   SING N N 8  
KSG C3  C4   SING N N 9  
KSG C3  O2   SING N N 10 
KSG C3  H3   SING N N 11 
KSG O2  HO2  SING N N 12 
KSG C4  O3   SING N N 13 
KSG C4  C5   SING N N 14 
KSG C4  H4   SING N N 15 
KSG O3  HO3  SING N N 16 
KSG C5  C6   SING N N 17 
KSG C5  O4   SING N N 18 
KSG C5  H5   SING N N 19 
KSG O4  HO4  SING N N 20 
KSG C6  O5   SING N N 21 
KSG C6  C7   SING N N 22 
KSG C6  H6   SING N N 23 
KSG O5  HO5  SING N N 24 
KSG C7  O6   SING N N 25 
KSG C7  H7   SING N N 26 
KSG O6  HO6  SING N N 27 
KSG O7  C8   SING N N 28 
KSG C8  C9   SING N N 29 
KSG C8  C10  SING N N 30 
KSG C8  H8   SING N N 31 
KSG C9  H91  SING N N 32 
KSG C9  H92  SING N N 33 
KSG C9  H93  SING N N 34 
KSG C10 C11  SING N N 35 
KSG C10 N2   SING N N 36 
KSG C10 H10  SING N N 37 
KSG C11 C12  SING N N 38 
KSG C11 H111 SING N N 39 
KSG C11 H112 SING N N 40 
KSG C12 N1   SING N N 41 
KSG C12 H12  SING N N 42 
KSG N1  HN11 SING N N 43 
KSG N1  HN12 SING N N 44 
KSG N2  C13  SING N N 45 
KSG N2  HN2  SING N N 46 
KSG C13 N3   DOUB N Z 47 
KSG C13 C14  SING N N 48 
KSG N3  HN3  SING N N 49 
KSG C14 O8   DOUB N N 50 
KSG C14 O9   SING N N 51 
KSG O9  HO9  SING N N 52 
# 
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 
KSG SMILES           ACDLabs              10.04 O=C(O)C(=[N@H])NC2C(OC(OC1C(O)C(O)C(O)C(O)C1O)C(N)C2)C                                                                                                                                                    
KSG InChI            InChI                1.02b InChI=1/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6-,7+,8+,9-,10+,11+,14-/m1/s1/f/h16-17,23H/b16-12- 
KSG InChIKey         InChI                1.02b PVTHJAPFENJVNC-OFAPFQPGDP                                                                                                                                                                                 
KSG SMILES_CANONICAL CACTVS               3.341 C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]2O)[C@@H](N)C[C@@H]1NC(=N)C(O)=O                                                                                                             
KSG SMILES           CACTVS               3.341 C[CH]1O[CH](O[CH]2[CH](O)[CH](O)[CH](O)[CH](O)[CH]2O)[CH](N)C[CH]1NC(=N)C(O)=O                                                                                                                            
KSG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/C(=O)O)\N[C@H]1C[C@@H]([C@H](O[C@@H]1C)OC2[C@H]([C@H](C([C@@H]([C@H]2O)O)O)O)O)N                                                                                                                 
KSG SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(C(=O)O)NC1CC(C(OC1C)OC2C(C(C(C(C2O)O)O)O)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 
KSG "SYSTEMATIC NAME" ACDLabs              10.04 "(1S,2R,3S,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-4-{[(Z)-carboxy(imino)methyl]amino}-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranoside" 
KSG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy-oxan-3-yl]amino]-2-imino-ethanoic acid"                    
# 
