data_ADV
# 
_chem_comp.id                                    ADV 
_chem_comp.name                                  "ALPHA-BETA METHYLENE ADP-RIBOSE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H25 N5 O13 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "AMPCPR; {[5-(6-AMINO-PURIN-9-YL)-3,4-DIHYDROXY-TETRAHYDRO-FURAN-2-YLMETHOXY]-HYDROXY-PHOSPHORYLMETHYL}-PHOSPHONIC ACID MONO-(3,4,5-TRIHYDROXY-TETRAHYDRO-FURAN-2-YLMETHYL) ESTER" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-12-07 
_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                        557.343 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     ADV 
_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        1KHZ 
_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 
ADV PA     PA   P 0 1 N N R 35.687 33.465 10.905 -1.310 0.404  -0.687  PA     ADV 1  
ADV "O5'"  O5*  O 0 1 N N N 34.994 33.533 9.568  -1.129 -0.381 0.705   "O5'"  ADV 2  
ADV "C5'"  C5*  C 0 1 N N N 34.531 32.327 8.847  -1.988 0.255  1.653   "C5'"  ADV 3  
ADV "C4'"  C4*  C 0 1 N N R 34.090 32.785 7.538  -1.862 -0.446 3.007   "C4'"  ADV 4  
ADV "O4'"  O4*  O 0 1 N N N 35.253 32.926 6.676  -0.508 -0.348 3.501   "O4'"  ADV 5  
ADV "C3'"  C3*  C 0 1 N N S 33.233 31.758 6.869  -2.723 0.271  4.070   "C3'"  ADV 6  
ADV "O3'"  O3*  O 0 1 N N N 31.830 32.084 7.022  -3.972 -0.401 4.241   "O3'"  ADV 7  
ADV "C2'"  C2*  C 0 1 N N R 33.672 31.806 5.319  -1.877 0.181  5.362   "C2'"  ADV 8  
ADV "O2'"  O2*  O 0 1 N N N 32.914 32.907 4.631  -2.579 -0.547 6.371   "O2'"  ADV 9  
ADV "C1'"  C1*  C 0 1 N N R 35.148 32.235 5.361  -0.605 -0.576 4.924   "C1'"  ADV 10 
ADV N9     N9   N 0 1 Y N N 36.057 30.979 5.373  0.572  -0.036 5.608   N9     ADV 11 
ADV C8     C8   C 0 1 Y N N 36.345 30.103 6.386  1.348  0.999  5.180   C8     ADV 12 
ADV N7     N7   N 0 1 Y N N 37.088 29.082 5.990  2.309  1.214  6.031   N7     ADV 13 
ADV C5     C5   C 0 1 Y N N 37.244 29.271 4.625  2.207  0.338  7.058   C5     ADV 14 
ADV C6     C6   C 0 1 Y N N 37.830 28.463 3.568  2.947  0.096  8.228   C6     ADV 15 
ADV N6     N6   N 0 1 N N N 38.258 27.217 3.768  4.056  0.864  8.536   N6     ADV 16 
ADV N1     N1   N 0 1 Y N N 37.801 28.969 2.245  2.553  -0.883 9.035   N1     ADV 17 
ADV C2     C2   C 0 1 Y N N 37.053 30.120 1.975  1.496  -1.621 8.749   C2     ADV 18 
ADV N3     N3   N 0 1 Y N N 36.384 30.862 2.868  0.777  -1.435 7.663   N3     ADV 19 
ADV C4     C4   C 0 1 Y N N 36.563 30.421 4.204  1.094  -0.479 6.796   C4     ADV 20 
ADV CX     CX   C 0 1 N N N 36.962 32.336 10.807 -0.241 -0.351 -1.956  CX     ADV 21 
ADV PB     PB   P 0 1 N N S 37.021 30.703 11.220 -0.447 0.538  -3.533  PB     ADV 22 
ADV O1B    O1B  O 0 1 N N N 36.447 29.940 10.090 -0.070 1.958  -3.352  O1B    ADV 23 
ADV OR5    OR5  O 0 1 N N N 38.596 30.263 11.372 0.496  -0.129 -4.653  OR5    ADV 24 
ADV CR5    CR5  C 0 1 N N N 39.225 30.464 12.825 0.291  0.608  -5.860  CR5    ADV 25 
ADV CR4    CR4  C 0 1 N N R 39.795 29.092 13.400 1.164  0.021  -6.971  CR4    ADV 26 
ADV OR4    OR4  O 0 1 N N N 38.667 27.991 13.428 0.790  -1.339 -7.215  OR4    ADV 27 
ADV CR3    CR3  C 0 1 N N S 40.877 28.597 12.375 0.945  0.809  -8.280  CR3    ADV 28 
ADV OR3    OR3  O 0 1 N N N 42.003 28.104 13.053 2.005  1.740  -8.505  OR3    ADV 29 
ADV CR2    CR2  C 0 1 N N R 40.185 27.455 11.592 0.963  -0.318 -9.349  CR2    ADV 30 
ADV OR2    OR2  O 0 1 N N N 41.066 26.477 11.274 2.300  -0.642 -9.733  OR2    ADV 31 
ADV CR1    CR1  C 0 1 N N S 39.076 26.888 12.520 0.310  -1.482 -8.562  CR1    ADV 32 
ADV OR1    OR1  O 0 1 N N N 39.628 25.825 13.323 0.718  -2.740 -9.103  OR1    ADV 33 
ADV O2A    O2A  O 0 1 N N N 36.197 34.766 11.203 -2.848 0.314  -1.158  O2A    ADV 34 
ADV O2B    O2B  O 0 1 N N N 36.241 30.426 12.438 -1.984 0.448  -4.004  O2B    ADV 35 
ADV O1A    O1A  O 0 1 N N N 34.764 33.095 11.892 -0.933 1.824  -0.506  O1A    ADV 36 
ADV "H5'1" 1H5* H 0 0 N N N 35.295 31.516 8.800  -3.019 0.194  1.307   "H5'1" ADV 37 
ADV "H5'2" 2H5* H 0 0 N N N 33.754 31.749 9.400  -1.700 1.301  1.759   "H5'2" ADV 38 
ADV "H'4"  4H*  H 0 1 N N N 33.531 33.738 7.686  -2.160 -1.491 2.920   "H'4"  ADV 39 
ADV "H'3"  3H*  H 0 1 N N N 33.365 30.742 7.309  -2.886 1.311  3.790   "H'3"  ADV 40 
ADV "HO'3" 3HO* H 0 0 N N N 31.285 31.431 6.597  -4.464 0.089  4.913   "HO'3" ADV 41 
ADV "H'2"  2H*  H 0 1 N N N 33.491 30.838 4.795  -1.621 1.178  5.721   "H'2"  ADV 42 
ADV "HO'2" 2HO* H 0 0 N N N 33.172 32.935 3.717  -3.391 -0.055 6.557   "HO'2" ADV 43 
ADV "H'1"  1H*  H 0 1 N N N 35.453 32.863 4.492  -0.708 -1.641 5.131   "H'1"  ADV 44 
ADV H8     H8   H 0 1 N N N 36.007 30.210 7.430  1.190  1.557  4.269   H8     ADV 45 
ADV H61    1H6  H 0 1 N N N 38.669 26.650 3.026  4.556  0.690  9.349   H61    ADV 46 
ADV H62    2H6  H 0 1 N N N 37.483 26.686 4.166  4.336  1.574  7.937   H62    ADV 47 
ADV H2     H2   H 0 1 N N N 36.982 30.485 0.936  1.211  -2.407 9.433   H2     ADV 48 
ADV HX1    1HX  H 0 1 N N N 37.294 32.373 9.743  0.798  -0.290 -1.637  HX1    ADV 49 
ADV HX2    2HX  H 0 1 N N N 37.800 32.803 11.373 -0.519 -1.396 -2.089  HX2    ADV 50 
ADV H5R1   1H5R H 0 0 N N N 40.001 31.264 12.828 -0.757 0.545  -6.150  H5R1   ADV 51 
ADV H5R2   2H5R H 0 0 N N N 38.495 30.931 13.526 0.561  1.651  -5.698  H5R2   ADV 52 
ADV HR4    4HR  H 0 1 N N N 40.192 29.249 14.429 2.213  0.070  -6.681  HR4    ADV 53 
ADV HR3    3HR  H 0 1 N N N 41.230 29.417 11.707 -0.019 1.318  -8.269  HR3    ADV 54 
ADV HOR3   3HOR H 0 0 N N N 42.657 27.804 12.433 1.854  2.131  -9.377  HOR3   ADV 55 
ADV HR2    2HR  H 0 1 N N N 39.762 27.840 10.634 0.362  -0.047 -10.218 HR2    ADV 56 
ADV HOR2   2HOR H 0 0 N N N 40.641 25.776 10.793 2.246  -1.417 -10.309 HOR2   ADV 57 
ADV HR1    1HR  H 0 1 N N N 38.217 26.501 11.923 -0.775 -1.394 -8.587  HR1    ADV 58 
ADV HOR1   1HOR H 0 0 N N N 39.889 25.119 12.742 0.320  -3.425 -8.549  HOR1   ADV 59 
ADV HOA2   2HOA H 0 0 N N N 36.633 34.723 12.045 -3.053 -0.624 -1.264  HOA2   ADV 60 
ADV HOB2   2HOB H 0 0 N N N 36.274 29.505 12.670 -2.189 -0.491 -4.110  HOB2   ADV 61 
# 
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 
ADV PA    "O5'"  SING N N 1  
ADV PA    CX     SING N N 2  
ADV PA    O2A    SING N N 3  
ADV PA    O1A    DOUB N N 4  
ADV "O5'" "C5'"  SING N N 5  
ADV "C5'" "C4'"  SING N N 6  
ADV "C5'" "H5'1" SING N N 7  
ADV "C5'" "H5'2" SING N N 8  
ADV "C4'" "O4'"  SING N N 9  
ADV "C4'" "C3'"  SING N N 10 
ADV "C4'" "H'4"  SING N N 11 
ADV "O4'" "C1'"  SING N N 12 
ADV "C3'" "O3'"  SING N N 13 
ADV "C3'" "C2'"  SING N N 14 
ADV "C3'" "H'3"  SING N N 15 
ADV "O3'" "HO'3" SING N N 16 
ADV "C2'" "O2'"  SING N N 17 
ADV "C2'" "C1'"  SING N N 18 
ADV "C2'" "H'2"  SING N N 19 
ADV "O2'" "HO'2" SING N N 20 
ADV "C1'" N9     SING N N 21 
ADV "C1'" "H'1"  SING N N 22 
ADV N9    C8     SING Y N 23 
ADV N9    C4     SING Y N 24 
ADV C8    N7     DOUB Y N 25 
ADV C8    H8     SING N N 26 
ADV N7    C5     SING Y N 27 
ADV C5    C6     DOUB Y N 28 
ADV C5    C4     SING Y N 29 
ADV C6    N6     SING N N 30 
ADV C6    N1     SING Y N 31 
ADV N6    H61    SING N N 32 
ADV N6    H62    SING N N 33 
ADV N1    C2     DOUB Y N 34 
ADV C2    N3     SING Y N 35 
ADV C2    H2     SING N N 36 
ADV N3    C4     DOUB Y N 37 
ADV CX    PB     SING N N 38 
ADV CX    HX1    SING N N 39 
ADV CX    HX2    SING N N 40 
ADV PB    O1B    DOUB N N 41 
ADV PB    OR5    SING N N 42 
ADV PB    O2B    SING N N 43 
ADV OR5   CR5    SING N N 44 
ADV CR5   CR4    SING N N 45 
ADV CR5   H5R1   SING N N 46 
ADV CR5   H5R2   SING N N 47 
ADV CR4   OR4    SING N N 48 
ADV CR4   CR3    SING N N 49 
ADV CR4   HR4    SING N N 50 
ADV OR4   CR1    SING N N 51 
ADV CR3   OR3    SING N N 52 
ADV CR3   CR2    SING N N 53 
ADV CR3   HR3    SING N N 54 
ADV OR3   HOR3   SING N N 55 
ADV CR2   OR2    SING N N 56 
ADV CR2   CR1    SING N N 57 
ADV CR2   HR2    SING N N 58 
ADV OR2   HOR2   SING N N 59 
ADV CR1   OR1    SING N N 60 
ADV CR1   HR1    SING N N 61 
ADV OR1   HOR1   SING N N 62 
ADV O2A   HOA2   SING N N 63 
ADV O2B   HOB2   SING N N 64 
# 
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 
ADV SMILES           ACDLabs              10.04 O=P(O)(OCC3OC(n1c2ncnc(N)c2nc1)C(O)C3O)CP(=O)(O)OCC4OC(O)C(O)C4O 
ADV InChI            InChI                1.02b 
InChI=1/C16H25N5O13P2/c17-13-8-14(19-3-18-13)21(4-20-8)15-11(24)9(22)6(33-15)1-31-35(27,28)5-36(29,30)32-2-7-10(23)12(25)16(26)34-7/h3-4,6-7,9-12,15-16,22-26H,1-2,5H2,(H,27,28)(H,29,30)(H2,17,18,19)/t6-,7-,9-,10-,11-,12-,15-,16+/m1/s1/f/h27,29H,17H2 
ADV InChIKey         InChI                1.02b ZPZRETFSCSWNDT-KDZOEFDMDJ 
ADV SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)C[P@@](O)(=O)OC[C@H]4O[C@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O 
ADV SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)C[P](O)(=O)OC[CH]4O[CH](O)[CH](O)[CH]4O)[CH](O)[CH]3O 
ADV 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)(C[P@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@H](O4)O)O)O)O)O)O)N 
ADV SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(CP(=O)(O)OCC4C(C(C(O4)O)O)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 
ADV "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3S,4R,5S)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl methanediylbis[hydrogen (R,S)-phosphonate] (non-preferred name)" 
ADV "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[hydroxy-[[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy]phosphoryl]methyl]phosphinic acid" 
# 
