data_LAQ
# 
_chem_comp.id                                    LAQ 
_chem_comp.name                                  "5'-O-[(R)-({5-[(3R)-1,2-DITHIOLAN-3-YL]PENTANOYL}OXY)(HYDROXY)PHOSPHORYL]ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H26 N5 O8 P S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         LIPOYL-AMP 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-12-27 
_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                        535.532 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LAQ 
_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        ? 
_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 
LAQ O2P    O2P  O 0 1 N N N 38.867 23.939 6.621  9.963  -3.783  0.672  O2P    LAQ 1  
LAQ P      P    P 0 1 N N R 39.210 25.298 6.068  8.378  -4.093  0.562  P      LAQ 2  
LAQ O1P    O1P  O 0 1 N N N 38.278 25.988 5.119  7.492  -2.889  0.706  O1P    LAQ 3  
LAQ O3P    O3P  O 0 1 N N N 39.428 26.206 7.379  8.264  -4.850  -0.864 O3P    LAQ 4  
LAQ C10    C10  C 0 1 N N N 39.750 27.618 7.372  7.118  -5.400  -1.352 C10    LAQ 5  
LAQ C11    C11  C 0 1 N N N 39.510 28.357 8.674  7.392  -6.017  -2.702 C11    LAQ 6  
LAQ C12    C12  C 0 1 N N N 40.170 29.729 8.698  6.134  -6.629  -3.315 C12    LAQ 7  
LAQ C13    C13  C 0 1 N N N 40.306 30.224 10.129 6.434  -7.285  -4.663 C13    LAQ 8  
LAQ C14    C14  C 0 1 N N N 40.947 31.604 10.167 5.169  -7.868  -5.291 C14    LAQ 9  
LAQ C15    C15  C 0 1 N N R 41.167 32.098 11.597 5.457  -8.492  -6.648 C15    LAQ 10 
LAQ S15    S15  S 0 1 N N N 42.318 31.145 12.535 3.939  -9.183  -7.375 S15    LAQ 11 
LAQ S17    S17  S 0 1 N N N 42.472 32.556 13.977 4.419  -8.845  -9.339 S17    LAQ 12 
LAQ C17    C17  C 0 1 N N N 42.222 33.977 12.967 6.038  -8.091  -9.045 C17    LAQ 13 
LAQ C16    C16  C 0 1 N N N 41.753 33.514 11.582 5.988  -7.468  -7.654 C16    LAQ 14 
LAQ O10    O10  O 0 1 N N N 40.200 28.148 6.357  6.040  -5.387  -0.777 O10    LAQ 15 
LAQ "O5'"  O5*  O 0 1 N N N 40.678 25.306 5.428  8.142  -5.277  1.640  "O5'"  LAQ 16 
LAQ "C5'"  C5*  C 0 1 N N N 41.789 24.648 6.036  8.948  -6.439  1.555  "C5'"  LAQ 17 
LAQ "C4'"  C4*  C 0 1 N N R 42.835 24.419 4.947  8.156  -7.628  2.070  "C4'"  LAQ 18 
LAQ "C3'"  C3*  C 0 1 N N S 44.031 23.592 5.387  8.925  -8.936  2.014  "C3'"  LAQ 19 
LAQ "O3'"  O3*  O 0 1 N N N 43.754 22.195 5.308  9.808  -9.081  3.106  "O3'"  LAQ 20 
LAQ "C2'"  C2*  C 0 1 N N R 45.101 24.038 4.407  7.810  -9.965  1.998  "C2'"  LAQ 21 
LAQ "O2'"  O2*  O 0 1 N N N 44.800 23.497 3.121  7.358  -10.257 3.319  "O2'"  LAQ 22 
LAQ "C1'"  C1*  C 0 1 N N R 44.805 25.517 4.271  6.697  -9.247  1.231  "C1'"  LAQ 23 
LAQ "O4'"  O4*  O 0 1 N N N 43.405 25.666 4.540  6.998  -7.835  1.245  "O4'"  LAQ 24 
LAQ N9     N9   N 0 1 Y N N 45.525 26.375 5.243  6.552  -9.701  -0.153 N9     LAQ 25 
LAQ C8     C8   C 0 1 Y N N 46.235 26.007 6.330  7.533  -9.706  -1.109 C8     LAQ 26 
LAQ N7     N7   N 0 1 Y N N 46.725 27.091 6.978  7.102  -10.172 -2.263 N7     LAQ 27 
LAQ C5     C5   C 0 1 Y N N 46.308 28.180 6.304  5.783  -10.482 -2.046 C5     LAQ 28 
LAQ C6     C6   C 0 1 Y N N 46.456 29.651 6.423  4.796  -11.009 -2.872 C6     LAQ 29 
LAQ N6     N6   N 0 1 N N N 47.158 30.217 7.435  5.075  -11.328 -4.212 N6     LAQ 30 
LAQ N1     N1   N 0 1 Y N N 45.861 30.421 5.483  3.555  -11.213 -2.367 N1     LAQ 31 
LAQ C2     C2   C 0 1 Y N N 45.148 29.912 4.466  3.346  -10.887 -1.069 C2     LAQ 32 
LAQ N3     N3   N 0 1 Y N N 44.980 28.588 4.301  4.217  -10.373 -0.174 N3     LAQ 33 
LAQ C4     C4   C 0 1 Y N N 45.525 27.696 5.164  5.421  -10.197 -0.739 C4     LAQ 34 
LAQ HO2P   HO2P H 0 0 N N N 38.795 23.315 5.908  10.288 -3.229  1.414  HO2P   LAQ 35 
LAQ H111   1H11 H 0 0 N N N 38.426 28.490 8.804  8.156  -6.792  -2.574 H111   LAQ 36 
LAQ H112   2H11 H 0 0 N N N 39.951 27.759 9.485  7.783  -5.235  -3.362 H112   LAQ 37 
LAQ H121   1H12 H 0 0 N N N 41.169 29.658 8.243  5.370  -5.852  -3.443 H121   LAQ 38 
LAQ H122   2H12 H 0 0 N N N 39.546 30.437 8.132  5.713  -7.373  -2.627 H122   LAQ 39 
LAQ H131   1H13 H 0 0 N N N 39.307 30.281 10.585 7.177  -8.080  -4.527 H131   LAQ 40 
LAQ H132   2H13 H 0 0 N N N 40.946 29.523 10.685 6.874  -6.544  -5.342 H132   LAQ 41 
LAQ H141   1H14 H 0 0 N N N 41.922 31.552 9.660  4.415  -7.081  -5.411 H141   LAQ 42 
LAQ H142   2H14 H 0 0 N N N 40.267 32.308 9.665  4.740  -8.630  -4.629 H142   LAQ 43 
LAQ H15    H15  H 0 1 N N N 40.171 32.030 12.059 6.177  -9.308  -6.522 H15    LAQ 44 
LAQ H171   1H17 H 0 0 N N N 43.164 34.538 12.873 6.250  -7.338  -9.809 H171   LAQ 45 
LAQ H172   2H17 H 0 0 N N N 41.464 34.633 13.421 6.810  -8.864  -9.101 H172   LAQ 46 
LAQ H161   1H16 H 0 0 N N N 42.617 33.525 10.902 6.991  -7.138  -7.361 H161   LAQ 47 
LAQ H162   2H16 H 0 0 N N N 40.959 34.200 11.252 5.359  -6.567  -7.665 H162   LAQ 48 
LAQ "H5'1" 1H5* H 0 0 N N N 41.472 23.686 6.466  9.236  -6.593  0.511  "H5'1" LAQ 49 
LAQ "H5'2" 2H5* H 0 0 N N N 42.204 25.260 6.850  9.849  -6.287  2.157  "H5'2" LAQ 50 
LAQ "H4'"  H4*  H 0 1 N N N 42.282 23.892 4.155  7.818  -7.409  3.090  "H4'"  LAQ 51 
LAQ "H3'"  H3*  H 0 1 N N N 44.324 23.742 6.437  9.497  -9.001  1.081  "H3'"  LAQ 52 
LAQ "HO3'" HO3* H 0 0 N N N 43.692 21.935 4.396  10.613 -9.491  2.755  "HO3'" LAQ 53 
LAQ "H2'"  H2*  H 0 1 N N N 46.117 23.760 4.723  8.119  -10.914 1.550  "H2'"  LAQ 54 
LAQ "HO2'" HO2* H 0 0 N N N 44.733 24.202 2.488  6.403  -10.438 3.264  "HO2'" LAQ 55 
LAQ "H1'"  H1*  H 0 1 N N N 45.123 25.834 3.267  5.712  -9.393  1.686  "H1'"  LAQ 56 
LAQ H8     H8   H 0 1 N N N 46.392 24.985 6.642  8.538  -9.360  -0.906 H8     LAQ 57 
LAQ HN61   1HN6 H 0 0 N N N 48.105 30.356 7.147  6.028  -11.436 -4.504 HN61   LAQ 58 
LAQ HN62   2HN6 H 0 0 N N N 46.749 31.098 7.672  4.327  -11.350 -4.879 HN62   LAQ 59 
LAQ H2     H2   H 0 1 N N N 44.694 30.588 3.757  2.341  -11.063 -0.699 H2     LAQ 60 
# 
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 
LAQ O2P   P      SING N N 1  
LAQ O2P   HO2P   SING N N 2  
LAQ P     O1P    DOUB N N 3  
LAQ P     "O5'"  SING N N 4  
LAQ P     O3P    SING N N 5  
LAQ O3P   C10    SING N N 6  
LAQ C10   O10    DOUB N N 7  
LAQ C10   C11    SING N N 8  
LAQ C11   C12    SING N N 9  
LAQ C11   H111   SING N N 10 
LAQ C11   H112   SING N N 11 
LAQ C12   C13    SING N N 12 
LAQ C12   H121   SING N N 13 
LAQ C12   H122   SING N N 14 
LAQ C13   C14    SING N N 15 
LAQ C13   H131   SING N N 16 
LAQ C13   H132   SING N N 17 
LAQ C14   C15    SING N N 18 
LAQ C14   H141   SING N N 19 
LAQ C14   H142   SING N N 20 
LAQ C15   C16    SING N N 21 
LAQ C15   S15    SING N N 22 
LAQ C15   H15    SING N N 23 
LAQ S15   S17    SING N N 24 
LAQ S17   C17    SING N N 25 
LAQ C17   C16    SING N N 26 
LAQ C17   H171   SING N N 27 
LAQ C17   H172   SING N N 28 
LAQ C16   H161   SING N N 29 
LAQ C16   H162   SING N N 30 
LAQ "O5'" "C5'"  SING N N 31 
LAQ "C5'" "C4'"  SING N N 32 
LAQ "C5'" "H5'1" SING N N 33 
LAQ "C5'" "H5'2" SING N N 34 
LAQ "C4'" "O4'"  SING N N 35 
LAQ "C4'" "C3'"  SING N N 36 
LAQ "C4'" "H4'"  SING N N 37 
LAQ "C3'" "C2'"  SING N N 38 
LAQ "C3'" "O3'"  SING N N 39 
LAQ "C3'" "H3'"  SING N N 40 
LAQ "O3'" "HO3'" SING N N 41 
LAQ "C2'" "O2'"  SING N N 42 
LAQ "C2'" "C1'"  SING N N 43 
LAQ "C2'" "H2'"  SING N N 44 
LAQ "O2'" "HO2'" SING N N 45 
LAQ "C1'" "O4'"  SING N N 46 
LAQ "C1'" N9     SING N N 47 
LAQ "C1'" "H1'"  SING N N 48 
LAQ N9    C4     SING Y N 49 
LAQ N9    C8     SING Y N 50 
LAQ C8    N7     DOUB Y N 51 
LAQ C8    H8     SING N N 52 
LAQ N7    C5     SING Y N 53 
LAQ C5    C4     DOUB Y N 54 
LAQ C5    C6     SING Y N 55 
LAQ C6    N1     DOUB Y N 56 
LAQ C6    N6     SING N N 57 
LAQ N6    HN61   SING N N 58 
LAQ N6    HN62   SING N N 59 
LAQ N1    C2     SING Y N 60 
LAQ C2    N3     DOUB Y N 61 
LAQ C2    H2     SING N N 62 
LAQ N3    C4     SING Y N 63 
# 
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 
LAQ SMILES           ACDLabs              10.04 O=P(O)(OCC3OC(n1c2ncnc(N)c2nc1)C(O)C3O)OC(=O)CCCCC4SSCC4 
LAQ InChI            InChI                1.02b 
InChI=1/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10-,11-,14-,15-,18-/m1/s1/f/h27H,19H2 
LAQ InChIKey         InChI                1.02b QWEGOCJRZOKSOE-HURDMGDCDZ 
LAQ SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@](O)(=O)OC(=O)CCCC[C@@H]4CCSS4)[C@@H](O)[C@H]3O 
LAQ SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)OC(=O)CCCC[CH]4CCSS4)[CH](O)[CH]3O 
LAQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(O)OC(=O)CCCC[C@@H]4CCSS4)O)O)N 
LAQ SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC(=O)CCCCC4CCSS4)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 
LAQ "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(R)-({5-[(3R)-1,2-dithiolan-3-yl]pentanoyl}oxy)(hydroxy)phosphoryl]adenosine"                                                
LAQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] 5-[(3R)-1,2-dithiolan-3-yl]pentanoate" 
# 
