data_AM2
# 
_chem_comp.id                                    AM2 
_chem_comp.name                                  APRAMYCIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C21 H41 N5 O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
"NEBRAMYCIN II, 4-O-(3ALPHA-AMINO-6ALPHA-((4-AMINO-4-DEOXY-ALPHA-D-GLUCOPYRANOSYL)OXY)-2,3,4,5ABETA,6,7,8,8AALPHA-OCTAHYDRO-8BETA-HYDROXY-7BETA-(METHYLAMINO)PYRANO(3,2-B)PYRAN-2ALPHA-YL)-2-DEOXY-D-STREPTAMINE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-02-17 
_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                        539.577 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AM2 
_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        1YRJ 
_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 
AM2 CA1  CA1  C 0 1 N N S 28.355 -2.367 35.495 2.810  -1.613 0.449  CA1  AM2 1  
AM2 CA2  CA2  C 0 1 N N R 28.660 -0.854 35.684 2.051  -2.834 -0.075 CA2  AM2 2  
AM2 CA3  CA3  C 0 1 N N N 27.367 -0.022 35.845 0.843  -2.356 -0.888 CA3  AM2 3  
AM2 CA4  CA4  C 0 1 N N S 26.446 -0.300 34.644 0.013  -1.391 -0.033 CA4  AM2 4  
AM2 CA5  CA5  C 0 1 N N R 26.119 -1.843 34.568 0.927  -0.286 0.505  CA5  AM2 5  
AM2 CA6  CA6  C 0 1 N N R 25.153 -2.192 33.396 0.098  0.675  1.367  CA6  AM2 6  
AM2 CA7  CA7  C 0 1 N N S 23.880 -1.287 33.454 -1.109 1.153  0.553  CA7  AM2 7  
AM2 CA8  CA8  C 0 1 N N R 24.292 0.253  33.588 -1.869 -0.066 0.026  CA8  AM2 8  
AM2 CA9  CA9  C 0 1 N N N 22.292 -2.931 32.267 -2.748 2.846  0.521  CA9  AM2 9  
AM2 OA4  OA4  O 0 1 N N N 27.381 -2.611 34.446 1.962  -0.853 1.307  OA4  AM2 10 
AM2 OA5  OA5  O 0 1 N N N 25.209 0.478  34.742 -1.020 -0.827 -0.840 OA5  AM2 11 
AM2 NA2  NA2  N 0 1 N N N 29.598 -0.610 36.832 2.937  -3.636 -0.929 NA2  AM2 12 
AM2 NA7  NA7  N 0 1 N N N 22.978 -1.598 32.279 -1.994 1.953  1.410  NA7  AM2 13 
AM2 OA6  OA6  O 0 1 N N N 25.840 -2.104 32.164 -0.354 -0.001 2.542  OA6  AM2 14 
AM2 OA8  OA8  O 0 1 N N N 23.157 1.120  33.779 -3.021 0.368  -0.699 OA8  AM2 15 
AM2 OA1  OA1  O 0 1 N N N 27.893 -3.006 36.679 3.223  -0.802 -0.652 OA1  AM2 16 
AM2 CB1  CB1  C 0 1 N N R 23.417 2.497  33.376 -3.812 -0.795 -0.955 CB1  AM2 17 
AM2 CB2  CB2  C 0 1 N N R 22.260 3.503  33.698 -4.928 -0.444 -1.941 CB2  AM2 18 
AM2 CB3  CB3  C 0 1 N N S 21.012 3.245  32.793 -5.789 0.675  -1.347 CB3  AM2 19 
AM2 CB4  CB4  C 0 1 N N S 21.457 3.371  31.303 -6.261 0.242  0.046  CB4  AM2 20 
AM2 CB5  CB5  C 0 1 N N S 22.598 2.314  30.990 -5.045 -0.160 0.883  CB5  AM2 21 
AM2 CB6  CB6  C 0 1 N N N 23.166 2.369  29.549 -5.505 -0.563 2.285  CB6  AM2 22 
AM2 OB1  OB1  O 0 1 N N N 23.727 2.525  31.907 -4.378 -1.261 0.268  OB1  AM2 23 
AM2 NB4  NB4  N 0 1 N N N 20.281 3.163  30.428 -6.961 1.357  0.698  NB4  AM2 24 
AM2 OB2  OB2  O 0 1 N N N 21.951 3.424  35.094 -4.356 -0.004 -3.174 OB2  AM2 25 
AM2 OB3  OB3  O 0 1 N N N 19.987 4.207  33.095 -6.921 0.911  -2.186 OB3  AM2 26 
AM2 OB6  OB6  O 0 1 N N N 22.476 1.509  28.623 -4.363 -0.820 3.106  OB6  AM2 27 
AM2 CC1  CC1  C 0 1 N N R 28.119 -4.459 36.825 4.205  0.107  -0.151 CC1  AM2 28 
AM2 CC2  CC2  C 0 1 N N R 29.571 -4.647 37.341 5.598  -0.502 -0.323 CC2  AM2 29 
AM2 CC3  CC3  C 0 1 N N S 29.872 -6.158 37.525 6.650  0.471  0.214  CC3  AM2 30 
AM2 CC4  CC4  C 0 1 N N R 28.877 -6.776 38.540 6.569  1.788  -0.561 CC4  AM2 31 
AM2 CC5  CC5  C 0 1 N N N 27.406 -6.619 38.019 5.176  2.397  -0.390 CC5  AM2 32 
AM2 CC6  CC6  C 0 1 N N S 27.110 -5.106 37.834 4.125  1.424  -0.927 CC6  AM2 33 
AM2 NC4  NC4  N 0 1 N N N 29.169 -8.202 38.725 7.579  2.722  -0.046 NC4  AM2 34 
AM2 NC6  NC6  N 0 1 N N N 25.736 -4.970 37.350 2.787  2.008  -0.762 NC6  AM2 35 
AM2 OC2  OC2  O 0 1 N N N 30.477 -4.071 36.391 5.673  -1.731 0.401  OC2  AM2 36 
AM2 OC3  OC3  O 0 1 N N N 31.204 -6.282 37.997 7.951  -0.097 0.054  OC3  AM2 37 
AM2 HA1  HA1  H 0 1 N N N 29.339 -2.805 35.209 3.688  -1.943 1.006  HA1  AM2 38 
AM2 HA2  HA2  H 0 1 N N N 29.169 -0.514 34.752 1.709  -3.439 0.765  HA2  AM2 39 
AM2 HA31 1HA3 H 0 0 N N N 26.861 -0.205 36.821 1.188  -1.839 -1.784 HA31 AM2 40 
AM2 HA32 2HA3 H 0 0 N N N 27.574 1.065  35.980 0.231  -3.213 -1.171 HA32 AM2 41 
AM2 HA4  HA4  H 0 1 N N N 26.974 0.009  33.712 -0.431 -1.933 0.802  HA4  AM2 42 
AM2 HA5  HA5  H 0 1 N N N 25.593 -2.124 35.510 1.368  0.260  -0.329 HA5  AM2 43 
AM2 HA6  HA6  H 0 1 N N N 24.798 -3.244 33.496 0.710  1.531  1.650  HA6  AM2 44 
AM2 HA7  HA7  H 0 1 N N N 23.283 -1.510 34.368 -0.767 1.760  -0.285 HA7  AM2 45 
AM2 HA8  HA8  H 0 1 N N N 24.795 0.499  32.624 -2.182 -0.688 0.865  HA8  AM2 46 
AM2 HA91 1HA9 H 0 0 N N N 21.627 -3.160 31.401 -2.055 3.486  -0.024 HA91 AM2 47 
AM2 HA92 2HA9 H 0 0 N N N 23.053 -3.738 32.371 -3.327 2.252  -0.187 HA92 AM2 48 
AM2 HA93 3HA9 H 0 0 N N N 21.719 -3.059 33.215 -3.423 3.464  1.113  HA93 AM2 49 
AM2 HA21 1HA2 H 0 0 N N N 29.798 0.382  36.956 3.716  -3.918 -0.354 HA21 AM2 50 
AM2 HA22 2HA2 H 0 0 N N N 30.456 -1.151 36.730 2.430  -4.476 -1.165 HA22 AM2 51 
AM2 H2   H2   H 0 1 N N N 23.501 -1.480 31.411 -1.399 2.540  1.974  H2   AM2 52 
AM2 H1   H1   H 0 1 N N N 25.251 -2.316 31.449 -0.877 0.637  3.047  H1   AM2 53 
AM2 HB1  HB1  H 0 1 N N N 24.285 2.843  33.983 -3.181 -1.574 -1.383 HB1  AM2 54 
AM2 HB2  HB2  H 0 1 N N N 22.592 4.542  33.468 -5.547 -1.324 -2.120 HB2  AM2 55 
AM2 HB3  HB3  H 0 1 N N N 20.599 2.225  32.977 -5.197 1.587  -1.265 HB3  AM2 56 
AM2 HB4  HB4  H 0 1 N N N 21.870 4.388  31.111 -6.937 -0.609 -0.047 HB4  AM2 57 
AM2 HB5  HB5  H 0 1 N N N 22.109 1.319  31.117 -4.360 0.684  0.955  HB5  AM2 58 
AM2 HB61 1HB6 H 0 0 N N N 23.184 3.418  29.172 -6.091 0.246  2.722  HB61 AM2 59 
AM2 HB62 2HB6 H 0 0 N N N 24.259 2.151  29.548 -6.117 -1.463 2.223  HB62 AM2 60 
AM2 HB41 1HB4 H 0 0 N N N 20.571 3.245  29.453 -7.750 1.585  0.114  HB41 AM2 61 
AM2 HB42 2HB4 H 0 0 N N N 19.510 3.791  30.657 -7.335 0.997  1.564  HB42 AM2 62 
AM2 H5   H5   H 0 1 N N N 21.249 4.034  35.289 -3.824 -0.736 -3.513 H5   AM2 63 
AM2 H6   H6   H 0 1 N N N 19.228 4.050  32.544 -6.578 1.181  -3.049 H6   AM2 64 
AM2 HB6  HB6  H 0 1 N N N 22.824 1.542  27.739 -4.697 -1.070 3.978  HB6  AM2 65 
AM2 HC1  HC1  H 0 1 N N N 27.964 -4.962 35.842 4.019  0.296  0.906  HC1  AM2 66 
AM2 HC2  HC2  H 0 1 N N N 29.693 -4.140 38.326 5.784  -0.691 -1.380 HC2  AM2 67 
AM2 HC3  HC3  H 0 1 N N N 29.757 -6.700 36.557 6.464  0.661  1.271  HC3  AM2 68 
AM2 HC4  HC4  H 0 1 N N N 28.986 -6.241 39.512 6.755  1.599  -1.619 HC4  AM2 69 
AM2 HC51 1HC5 H 0 0 N N N 27.214 -7.209 37.092 5.119  3.335  -0.942 HC51 AM2 70 
AM2 HC52 2HC5 H 0 0 N N N 26.661 -7.123 38.678 4.990  2.586  0.667  HC52 AM2 71 
AM2 HC6  HC6  H 0 1 N N N 27.228 -4.573 38.806 4.311  1.234  -1.984 HC6  AM2 72 
AM2 HC41 1HC4 H 0 0 N N N 28.514 -8.608 39.393 7.490  3.571  -0.584 HC41 AM2 73 
AM2 HC42 2HC4 H 0 0 N N N 30.139 -8.361 38.995 7.309  2.948  0.900  HC42 AM2 74 
AM2 HC61 1HC6 H 0 0 N N N 25.079 -5.391 38.006 2.818  2.925  -1.182 HC61 AM2 75 
AM2 HC62 2HC6 H 0 0 N N N 25.626 -5.350 36.409 2.157  1.453  -1.322 HC62 AM2 76 
AM2 H3   H3   H 0 1 N N N 31.365 -4.186 36.706 6.565  -2.081 0.267  H3   AM2 77 
AM2 H4   H4   H 0 1 N N N 31.388 -7.207 38.109 7.959  -0.923 0.557  H4   AM2 78 
# 
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 
AM2 CA1 CA2  SING N N 1  
AM2 CA1 OA4  SING N N 2  
AM2 CA1 OA1  SING N N 3  
AM2 CA1 HA1  SING N N 4  
AM2 CA2 CA3  SING N N 5  
AM2 CA2 NA2  SING N N 6  
AM2 CA2 HA2  SING N N 7  
AM2 CA3 CA4  SING N N 8  
AM2 CA3 HA31 SING N N 9  
AM2 CA3 HA32 SING N N 10 
AM2 CA4 CA5  SING N N 11 
AM2 CA4 OA5  SING N N 12 
AM2 CA4 HA4  SING N N 13 
AM2 CA5 CA6  SING N N 14 
AM2 CA5 OA4  SING N N 15 
AM2 CA5 HA5  SING N N 16 
AM2 CA6 CA7  SING N N 17 
AM2 CA6 OA6  SING N N 18 
AM2 CA6 HA6  SING N N 19 
AM2 CA7 CA8  SING N N 20 
AM2 CA7 NA7  SING N N 21 
AM2 CA7 HA7  SING N N 22 
AM2 CA8 OA5  SING N N 23 
AM2 CA8 OA8  SING N N 24 
AM2 CA8 HA8  SING N N 25 
AM2 CA9 NA7  SING N N 26 
AM2 CA9 HA91 SING N N 27 
AM2 CA9 HA92 SING N N 28 
AM2 CA9 HA93 SING N N 29 
AM2 NA2 HA21 SING N N 30 
AM2 NA2 HA22 SING N N 31 
AM2 NA7 H2   SING N N 32 
AM2 OA6 H1   SING N N 33 
AM2 OA8 CB1  SING N N 34 
AM2 OA1 CC1  SING N N 35 
AM2 CB1 CB2  SING N N 36 
AM2 CB1 OB1  SING N N 37 
AM2 CB1 HB1  SING N N 38 
AM2 CB2 CB3  SING N N 39 
AM2 CB2 OB2  SING N N 40 
AM2 CB2 HB2  SING N N 41 
AM2 CB3 CB4  SING N N 42 
AM2 CB3 OB3  SING N N 43 
AM2 CB3 HB3  SING N N 44 
AM2 CB4 CB5  SING N N 45 
AM2 CB4 NB4  SING N N 46 
AM2 CB4 HB4  SING N N 47 
AM2 CB5 CB6  SING N N 48 
AM2 CB5 OB1  SING N N 49 
AM2 CB5 HB5  SING N N 50 
AM2 CB6 OB6  SING N N 51 
AM2 CB6 HB61 SING N N 52 
AM2 CB6 HB62 SING N N 53 
AM2 NB4 HB41 SING N N 54 
AM2 NB4 HB42 SING N N 55 
AM2 OB2 H5   SING N N 56 
AM2 OB3 H6   SING N N 57 
AM2 OB6 HB6  SING N N 58 
AM2 CC1 CC2  SING N N 59 
AM2 CC1 CC6  SING N N 60 
AM2 CC1 HC1  SING N N 61 
AM2 CC2 CC3  SING N N 62 
AM2 CC2 OC2  SING N N 63 
AM2 CC2 HC2  SING N N 64 
AM2 CC3 CC4  SING N N 65 
AM2 CC3 OC3  SING N N 66 
AM2 CC3 HC3  SING N N 67 
AM2 CC4 CC5  SING N N 68 
AM2 CC4 NC4  SING N N 69 
AM2 CC4 HC4  SING N N 70 
AM2 CC5 CC6  SING N N 71 
AM2 CC5 HC51 SING N N 72 
AM2 CC5 HC52 SING N N 73 
AM2 CC6 NC6  SING N N 74 
AM2 CC6 HC6  SING N N 75 
AM2 NC4 HC41 SING N N 76 
AM2 NC4 HC42 SING N N 77 
AM2 NC6 HC61 SING N N 78 
AM2 NC6 HC62 SING N N 79 
AM2 OC2 H3   SING N N 80 
AM2 OC3 H4   SING N N 81 
# 
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 
AM2 SMILES           ACDLabs              10.04 O3C(OC1OC(CO)C(N)C(O)C1O)C(NC)C(O)C4OC(OC2C(N)CC(N)C(O)C2O)C(N)CC34 
AM2 InChI            InChI                1.02b 
InChI=1/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1 
AM2 InChIKey         InChI                1.02b XZNUGFQTQHRASN-XQENGBIVBA 
AM2 SMILES_CANONICAL CACTVS               3.341 CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]4O[C@H](CO)[C@@H](N)[C@H](O)[C@H]4O 
AM2 SMILES           CACTVS               3.341 CN[CH]1[CH](O)[CH]2O[CH](O[CH]3[CH](N)C[CH](N)[CH](O)[CH]3O)[CH](N)C[CH]2O[CH]1O[CH]4O[CH](CO)[CH](N)[CH](O)[CH]4O 
AM2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O 
AM2 SMILES           "OpenEye OEToolkits" 1.5.0 CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)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 
AM2 "SYSTEMATIC NAME" ACDLabs              10.04 
"(2R,3R,4S,5S,6S)-5-amino-2-{[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (non-preferred name)" 
AM2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyl]oxy-4-hydroxy-3-methylamino-2,3,4,4a,6,7,8,8a-octahydropyrano[2,3-e]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol 
# 
