data_LAM
# 
_chem_comp.id                                    LAM 
_chem_comp.name                                  "4'-NITROPHENYL-S-(BETA-D-GLUCOPYRANOSYL)-(1-3)-(3-THIO-BETA-D-GLUCOPYRANOSYL)-(1-3)-BETA-D-GLUCOPYRANOSIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAS 
_chem_comp.formula                               "C24 H35 N O17 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "4'-NITROPHENYL-3I-THIOLAMINARITRIOSIDE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-06-04 
_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                        641.596 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LAM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
LAM C1     C1     C 0  1 N N S 35.821 25.646 26.370 -1.024 -3.096 0.477  C1     LAM 1  
LAM C2     C2     C 0  1 N N R 36.898 24.874 25.408 -2.194 -3.950 -0.020 C2     LAM 2  
LAM O2     O2     O 0  1 N N N 37.991 25.846 25.057 -2.978 -3.196 -0.944 O2     LAM 3  
LAM C3     C3     C 0  1 N N S 36.212 24.275 24.064 -3.094 -4.375 1.144  C3     LAM 4  
LAM O3     O3     O 0  1 N N N 37.143 23.355 23.383 -4.008 -5.365 0.666  O3     LAM 5  
LAM C4     C4     C 0  1 N N R 34.857 23.470 24.426 -2.277 -4.958 2.298  C4     LAM 6  
LAM O4     O4     O 0  1 N N N 34.362 22.942 23.249 -3.148 -5.130 3.412  O4     LAM 7  
LAM C5     C5     C 0  1 N N R 33.842 24.579 25.119 -1.118 -4.027 2.662  C5     LAM 8  
LAM O5     O5     O 0  1 N N N 34.522 24.978 26.430 -0.311 -3.775 1.511  O5     LAM 9  
LAM C6     C6     C 0  1 N N N 32.347 24.224 25.494 -0.207 -4.631 3.726  C6     LAM 10 
LAM O6     O6     O 0  1 N N N 32.268 23.660 26.871 0.839  -3.715 3.996  O6     LAM 11 
LAM C1A    C1A    C 0  1 N N S 35.790 28.360 30.952 1.652  0.431  1.328  C1A    LAM 12 
LAM C2A    C2A    C 0  1 N N S 36.493 27.402 29.749 0.630  -0.537 0.721  C2A    LAM 13 
LAM C3A    C3A    C 0  1 N N S 35.377 26.357 29.067 1.333  -1.718 0.042  C3A    LAM 14 
LAM C4A    C4A    C 0  1 N N R 34.610 25.439 30.180 2.455  -1.236 -0.889 C4A    LAM 15 
LAM C5A    C5A    C 0  1 N N R 33.991 26.423 31.455 3.372  -0.245 -0.160 C5A    LAM 16 
LAM C6A    C6A    C 0  1 N N N 33.516 25.567 32.737 4.431  0.337  -1.092 C6A    LAM 17 
LAM O1A    O1A    O 0  1 N N N 36.778 29.368 31.560 0.983  1.572  1.866  O1A    LAM 18 
LAM O2A    O2A    O 0  1 N N N 37.205 28.224 28.640 -0.212 -1.027 1.763  O2A    LAM 19 
LAM O4A    O4A    O 0  1 N N N 33.573 24.525 29.434 3.225  -2.345 -1.346 O4A    LAM 20 
LAM S3A    S3A    S 0  1 N N N 36.331 25.200 28.048 0.113  -2.712 -0.904 S3A    LAM 21 
LAM O5A    O5A    O 0  1 N N N 35.013 27.495 32.026 2.607  0.846  0.356  O5A    LAM 22 
LAM O6A    O6A    O 0  1 N N N 32.311 24.832 32.387 5.228  1.246  -0.356 O6A    LAM 23 
LAM C1B    C1B    C 0  1 N N S ?      ?      ?      -0.248 1.841  4.592  C1B    LAM 24 
LAM C2B    C2B    C 0  1 N N S ?      ?      ?      1.206  1.468  4.282  C2B    LAM 25 
LAM C3B    C3B    C 0  1 N N S ?      ?      ?      1.693  2.111  2.982  C3B    LAM 26 
LAM C4B    C4B    C 0  1 N N S ?      ?      ?      1.446  3.621  3.055  C4B    LAM 27 
LAM C5B    C5B    C 0  1 N N S ?      ?      ?      -0.023 3.917  3.403  C5B    LAM 28 
LAM C6B    C6B    C 0  1 N N N ?      ?      ?      -0.276 5.409  3.601  C6B    LAM 29 
LAM O1B    O1B    O 0  1 N N N ?      ?      ?      -1.140 1.234  3.660  O1B    LAM 30 
LAM O2B    O2B    O 0  1 N N N ?      ?      ?      1.344  0.055  4.231  O2B    LAM 31 
LAM O4B    O4B    O 0  1 N N N ?      ?      ?      1.813  4.208  1.813  O4B    LAM 32 
LAM O5B    O5B    O 0  1 N N N ?      ?      ?      -0.393 3.264  4.626  O5B    LAM 33 
LAM O6B    O6B    O 0  1 N N N ?      ?      ?      -1.646 5.596  3.905  O6B    LAM 34 
LAM "C1'"  "C1'"  C 0  1 Y N N ?      ?      ?      -2.388 0.915  4.124  "C1'"  LAM 35 
LAM "C2'"  "C2'"  C 0  1 Y N N ?      ?      ?      -2.963 1.675  5.136  "C2'"  LAM 36 
LAM "C3'"  "C3'"  C 0  1 Y N N ?      ?      ?      -4.233 1.347  5.610  "C3'"  LAM 37 
LAM "C4'"  "C4'"  C 0  1 Y N N ?      ?      ?      -4.921 0.261  5.069  "C4'"  LAM 38 
LAM "C5'"  "C5'"  C 0  1 Y N N ?      ?      ?      -4.338 -0.497 4.054  "C5'"  LAM 39 
LAM "C6'"  "C6'"  C 0  1 Y N N ?      ?      ?      -3.068 -0.170 3.580  "C6'"  LAM 40 
LAM "N4'"  "N4'"  N 1  1 N N N ?      ?      ?      -6.215 -0.071 5.551  "N4'"  LAM 41 
LAM "O'5"  "1O4'" O 0  1 N N N ?      ?      ?      -6.816 -1.052 5.050  "O'5"  LAM 42 
LAM "O'6"  "2O4'" O -1 1 N N N ?      ?      ?      -6.722 0.625  6.463  "O'6"  LAM 43 
LAM H11    1H1    H 0  1 N N N 35.776 26.692 26.031 -1.381 -2.130 0.855  H11    LAM 44 
LAM H21    1H2    H 0  1 N N N 37.306 24.011 25.954 -1.830 -4.847 -0.539 H21    LAM 45 
LAM HO21   1HO2   H 0  0 N N N 37.948 26.051 24.130 -2.390 -2.520 -1.315 HO21   LAM 46 
LAM H31    1H3    H 0  1 N N N 35.970 25.119 23.402 -3.704 -3.529 1.485  H31    LAM 47 
LAM HO31   1HO3   H 0  0 N N N 36.814 23.157 22.514 -4.414 -4.997 -0.133 HO31   LAM 48 
LAM H41    1H4    H 0  1 N N N 34.999 22.633 25.126 -1.906 -5.949 2.006  H41    LAM 49 
LAM HO41   1HO4   H 0  0 N N N 34.248 23.638 22.612 -4.053 -5.062 3.069  HO41   LAM 50 
LAM H51    1H5    H 0  1 N N N 33.709 25.326 24.323 -1.499 -3.075 3.053  H51    LAM 51 
LAM H61    1H6    H 0  1 N N N 31.738 25.139 25.445 0.218  -5.567 3.365  H61    LAM 52 
LAM H62    2H6    H 0  1 N N N 31.972 23.474 24.782 -0.772 -4.812 4.641  H62    LAM 53 
LAM HO61   1HO6   H 0  0 N N N 32.251 22.711 26.825 0.625  -2.891 3.527  HO61   LAM 54 
LAM H1A1   1H1A   H 0  0 N N N 35.023 28.978 30.462 2.174  -0.037 2.172  H1A1   LAM 55 
LAM H2A1   1H2A   H 0  0 N N N 37.270 26.815 30.260 -0.002 0.009  0.010  H2A1   LAM 56 
LAM H3A1   1H3A   H 0  0 N N N 34.629 26.952 28.523 1.741  -2.402 0.797  H3A1   LAM 57 
LAM H4A1   1H4A   H 0  0 N N N 35.295 24.753 30.700 2.022  -0.739 -1.767 H4A1   LAM 58 
LAM H5A1   1H5A   H 0  0 N N N 33.149 26.929 30.961 3.900  -0.742 0.664  H5A1   LAM 59 
LAM H6A1   1H6A   H 0  0 N N N 34.309 24.863 33.028 3.951  0.863  -1.917 H6A1   LAM 60 
LAM H6A2   2H6A   H 0  0 N N N 33.311 26.241 33.582 5.061  -0.462 -1.482 H6A2   LAM 61 
LAM HA21   1HA2   H 0  0 N N N 37.350 29.111 28.947 -0.008 -0.500 2.551  HA21   LAM 62 
LAM HA41   1HA4   H 0  0 N N N 32.841 24.340 30.010 4.152  -2.061 -1.334 HA41   LAM 63 
LAM HA61   1HA6   H 0  0 N N N 31.798 24.672 33.171 5.914  1.579  -0.960 HA61   LAM 64 
LAM H1B1   1H1B   H 0  0 N N N ?      ?      ?      -0.523 1.455  5.578  H1B1   LAM 65 
LAM H2B1   1H2B   H 0  0 N N N ?      ?      ?      1.841  1.832  5.099  H2B1   LAM 66 
LAM H3B1   1H3B   H 0  0 N N N ?      ?      ?      2.751  1.891  2.805  H3B1   LAM 67 
LAM H4B1   1H4B   H 0  0 N N N ?      ?      ?      2.095  4.045  3.831  H4B1   LAM 68 
LAM H5B1   1H5B   H 0  0 N N N ?      ?      ?      -0.687 3.584  2.596  H5B1   LAM 69 
LAM H6B1   1H6B   H 0  0 N N N ?      ?      ?      -0.032 5.952  2.688  H6B1   LAM 70 
LAM H6B2   2H6B   H 0  0 N N N ?      ?      ?      0.331  5.782  4.425  H6B2   LAM 71 
LAM HB21   1HB2   H 0  0 N N N ?      ?      ?      2.115  -0.171 4.777  HB21   LAM 72 
LAM HB41   1HB4   H 0  0 N N N ?      ?      ?      2.649  4.678  1.962  HB41   LAM 73 
LAM HB61   1HB6   H 0  0 N N N ?      ?      ?      -2.134 5.551  3.065  HB61   LAM 74 
LAM "H2'1" "1H2'" H 0  0 N N N ?      ?      ?      -2.432 2.522  5.562  "H2'1" LAM 75 
LAM "H3'1" "1H3'" H 0  0 N N N ?      ?      ?      -4.676 1.947  6.402  "H3'1" LAM 76 
LAM "H5'1" "1H5'" H 0  0 N N N ?      ?      ?      -4.863 -1.347 3.624  "H5'1" LAM 77 
LAM "H6'1" "1H6'" H 0  0 N N N ?      ?      ?      -2.618 -0.765 2.790  "H6'1" LAM 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 
LAM C1    C2     SING N N 1  
LAM C1    O5     SING N N 2  
LAM C1    S3A    SING N N 3  
LAM C1    H11    SING N N 4  
LAM C2    O2     SING N N 5  
LAM C2    C3     SING N N 6  
LAM C2    H21    SING N N 7  
LAM O2    HO21   SING N N 8  
LAM C3    O3     SING N N 9  
LAM C3    C4     SING N N 10 
LAM C3    H31    SING N N 11 
LAM O3    HO31   SING N N 12 
LAM C4    O4     SING N N 13 
LAM C4    C5     SING N N 14 
LAM C4    H41    SING N N 15 
LAM O4    HO41   SING N N 16 
LAM C5    O5     SING N N 17 
LAM C5    C6     SING N N 18 
LAM C5    H51    SING N N 19 
LAM C6    O6     SING N N 20 
LAM C6    H61    SING N N 21 
LAM C6    H62    SING N N 22 
LAM O6    HO61   SING N N 23 
LAM C1A   C2A    SING N N 24 
LAM C1A   O1A    SING N N 25 
LAM C1A   O5A    SING N N 26 
LAM C1A   H1A1   SING N N 27 
LAM C2A   C3A    SING N N 28 
LAM C2A   O2A    SING N N 29 
LAM C2A   H2A1   SING N N 30 
LAM C3A   C4A    SING N N 31 
LAM C3A   S3A    SING N N 32 
LAM C3A   H3A1   SING N N 33 
LAM C4A   C5A    SING N N 34 
LAM C4A   O4A    SING N N 35 
LAM C4A   H4A1   SING N N 36 
LAM C5A   C6A    SING N N 37 
LAM C5A   O5A    SING N N 38 
LAM C5A   H5A1   SING N N 39 
LAM C6A   O6A    SING N N 40 
LAM C6A   H6A1   SING N N 41 
LAM C6A   H6A2   SING N N 42 
LAM O1A   C3B    SING N N 43 
LAM O2A   HA21   SING N N 44 
LAM O4A   HA41   SING N N 45 
LAM O6A   HA61   SING N N 46 
LAM C1B   C2B    SING N N 47 
LAM C1B   O1B    SING N N 48 
LAM C1B   O5B    SING N N 49 
LAM C1B   H1B1   SING N N 50 
LAM C2B   C3B    SING N N 51 
LAM C2B   O2B    SING N N 52 
LAM C2B   H2B1   SING N N 53 
LAM C3B   C4B    SING N N 54 
LAM C3B   H3B1   SING N N 55 
LAM C4B   C5B    SING N N 56 
LAM C4B   O4B    SING N N 57 
LAM C4B   H4B1   SING N N 58 
LAM C5B   C6B    SING N N 59 
LAM C5B   O5B    SING N N 60 
LAM C5B   H5B1   SING N N 61 
LAM C6B   O6B    SING N N 62 
LAM C6B   H6B1   SING N N 63 
LAM C6B   H6B2   SING N N 64 
LAM O1B   "C1'"  SING N N 65 
LAM O2B   HB21   SING N N 66 
LAM O4B   HB41   SING N N 67 
LAM O6B   HB61   SING N N 68 
LAM "C1'" "C2'"  DOUB Y N 69 
LAM "C1'" "C6'"  SING Y N 70 
LAM "C2'" "C3'"  SING Y N 71 
LAM "C2'" "H2'1" SING N N 72 
LAM "C3'" "C4'"  DOUB Y N 73 
LAM "C3'" "H3'1" SING N N 74 
LAM "C4'" "C5'"  SING Y N 75 
LAM "C4'" "N4'"  SING N N 76 
LAM "C5'" "C6'"  DOUB Y N 77 
LAM "C5'" "H5'1" SING N N 78 
LAM "C6'" "H6'1" SING N N 79 
LAM "N4'" "O'5"  DOUB N N 80 
LAM "N4'" "O'6"  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 
LAM SMILES           ACDLabs              10.04 [O-][N+](=O)c4ccc(OC3OC(CO)C(O)C(OC2OC(CO)C(O)C(SC1OC(C(O)C(O)C1O)CO)C2O)C3O)cc4 
LAM InChI            InChI                1.02b 
InChI=1/C24H35NO17S/c26-5-10-13(29)16(32)17(33)24(41-10)43-21-15(31)12(7-28)40-23(19(21)35)42-20-14(30)11(6-27)39-22(18(20)34)38-9-3-1-8(2-4-9)25(36)37/h1-4,10-24,26-35H,5-7H2/t10-,11?,12-,13-,14?,15-,16+,17-,18?,19-,20?,21+,22?,23+,24+/m1/s1 
LAM InChIKey         InChI                1.02b VWNONHZCCMYIGR-VGNFVTAUBL 
LAM SMILES_CANONICAL CACTVS               3.341 OCC1OC(Oc2ccc(cc2)[N+]([O-])=O)C(O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](S[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)C1O 
LAM SMILES           CACTVS               3.341 OCC1OC(Oc2ccc(cc2)[N+]([O-])=O)C(O)C(O[CH]3O[CH](CO)[CH](O)[CH](S[CH]4O[CH](CO)[CH](O)[CH](O)[CH]4O)[CH]3O)C1O 
LAM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[N+](=O)[O-])O[C@H]2[C@H]([C@H]([C@H]([C@@H](O2)CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)S[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O 
LAM SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)OC3C(C(C(C(O3)CO)O)SC4C(C(C(C(O4)CO)O)O)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 
LAM "SYSTEMATIC NAME" ACDLabs              10.04 "4-nitrophenyl beta-D-glucopyranosyl-(1->3)-3-thio-beta-D-glucopyranosyl-(1->3)hexopyranoside" 
LAM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
(2S,3R,4S,5S,6R)-2-[(2S,3S,4S,5R,6R)-2-[(2S,3S,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]sulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol 
# 
