data_4AD # _chem_comp.id 4AD _chem_comp.name "4-AMINO-1,4-DIOXOBUTAN-2-AMINIUM ADENOSINE-5'-MONOPHOSPHATE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C14 H21 N7 O9 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ASNAMP _chem_comp.pdbx_formal_charge 1 _chem_comp.pdbx_initial_date 2005-05-20 _chem_comp.pdbx_modified_date 2021-03-01 _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 462.332 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 4AD _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 1X54 _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 4AD O2P O2P O 0 1 N N N -1.420 8.770 41.940 2.964 -2.612 -0.628 O2P 4AD 1 4AD P P P 0 1 N N R -2.791 9.305 41.680 2.565 -1.196 -0.470 P 4AD 2 4AD O1P O1P O 0 1 N N N -3.003 10.783 41.502 2.259 -0.560 -1.917 O1P 4AD 3 4AD O3P O3P O 0 1 N N N -3.661 8.789 42.943 3.758 -0.377 0.235 O3P 4AD 4 4AD C C C 0 1 N N N -5.061 9.002 43.156 4.990 -0.394 -0.298 C 4AD 5 4AD O O O 0 1 N N N -5.754 9.720 42.428 5.203 -1.023 -1.307 O 4AD 6 4AD CA CA C 0 1 N N S -5.585 8.278 44.348 6.107 0.373 0.362 CA 4AD 7 4AD N N N 1 1 N N N -6.722 8.992 44.897 7.399 -0.159 -0.089 N 4AD 8 4AD CB CB C 0 1 N N N -5.958 6.890 43.825 6.004 1.852 -0.016 CB 4AD 9 4AD CG CG C 0 1 N N N -6.517 6.044 44.941 7.044 2.637 0.740 CG 4AD 10 4AD OD1 OD1 O 0 1 N N N -5.828 5.777 45.918 7.794 2.070 1.506 OD1 4AD 11 4AD ND2 ND2 N 0 1 N N N -7.772 5.612 44.784 7.141 3.970 0.565 ND2 4AD 12 4AD "O5'" O5* O 0 1 N N N -3.488 8.579 40.425 1.242 -1.111 0.443 "O5'" 4AD 13 4AD "C5'" C5* C 0 1 N N N -3.606 7.151 40.388 0.260 -1.948 -0.171 "C5'" 4AD 14 4AD "C4'" C4* C 0 1 N N R -3.098 6.698 39.026 -1.029 -1.911 0.652 "C4'" 4AD 15 4AD "C3'" C3* C 0 1 N N S -1.633 7.033 38.740 -2.054 -2.901 0.065 "C3'" 4AD 16 4AD "O3'" O3* O 0 1 N N N -0.769 6.026 39.284 -2.413 -3.892 1.030 "O3'" 4AD 17 4AD "C2'" C2* C 0 1 N N R -1.594 7.035 37.229 -3.278 -2.013 -0.283 "C2'" 4AD 18 4AD "O2'" O2* O 0 1 N N N -1.515 5.674 36.770 -4.498 -2.672 0.061 "O2'" 4AD 19 4AD "C1'" C1* C 0 1 N N R -2.961 7.572 36.856 -3.045 -0.773 0.618 "C1'" 4AD 20 4AD "O4'" O4* O 0 1 N N N -3.814 7.367 37.981 -1.612 -0.599 0.588 "O4'" 4AD 21 4AD N9 N9 N 0 1 Y N N -2.937 9.004 36.454 -3.719 0.404 0.064 N9 4AD 22 4AD C4 C4 C 0 1 Y N N -2.983 9.504 35.230 -5.008 0.798 0.322 C4 4AD 23 4AD N3 N3 N 0 1 Y N N -3.056 8.900 34.027 -5.997 0.334 1.079 N3 4AD 24 4AD C2 C2 C 0 1 Y N N -3.103 9.668 32.928 -7.156 0.957 1.125 C2 4AD 25 4AD N1 N1 N 0 1 Y N N -3.066 11.010 33.029 -7.395 2.060 0.440 N1 4AD 26 4AD C6 C6 C 0 1 Y N N -2.974 11.667 34.216 -6.464 2.601 -0.340 C6 4AD 27 4AD N6 N6 N 0 1 N N N -2.950 13.024 34.240 -6.724 3.758 -1.055 N6 4AD 28 4AD C5 C5 C 0 1 Y N N -2.929 10.906 35.387 -5.211 1.972 -0.422 C5 4AD 29 4AD N7 N7 N 0 1 Y N N -2.846 11.241 36.715 -4.059 2.225 -1.090 N7 4AD 30 4AD C8 C8 C 0 1 Y N N -2.844 10.003 37.502 -3.183 1.306 -0.806 C8 4AD 31 4AD HOP1 1HOP H 0 0 N N N -3.874 11.123 41.337 2.003 0.361 -1.770 HOP1 4AD 32 4AD HA HA H 0 1 N N N -4.858 8.202 45.170 6.029 0.268 1.445 HA 4AD 33 4AD HN1 1HN H 0 1 N N N -7.550 8.445 44.773 8.147 0.354 0.353 HN1 4AD 34 4AD HN2 2HN H 0 1 N N N -6.826 9.867 44.424 7.467 -1.135 0.160 HN2 4AD 35 4AD HN3 3HN H 0 1 N N N -6.574 9.156 45.872 7.471 -0.063 -1.091 HN3 4AD 36 4AD HB1 1HB H 0 1 N N N -5.057 6.404 43.424 5.011 2.224 0.239 HB1 4AD 37 4AD HB2 2HB H 0 1 N N N -6.716 6.993 43.034 6.170 1.965 -1.087 HB2 4AD 38 4AD HD21 1HD2 H 0 0 N N N -8.366 5.798 44.001 7.811 4.476 1.051 HD21 4AD 39 4AD HD22 2HD2 H 0 0 N N N -8.010 5.070 45.590 6.544 4.423 -0.051 HD22 4AD 40 4AD "H5'1" 1H5* H 0 0 N N N -4.650 6.840 40.540 0.057 -1.590 -1.180 "H5'1" 4AD 41 4AD "H5'2" 2H5* H 0 0 N N N -3.005 6.697 41.190 0.633 -2.971 -0.217 "H5'2" 4AD 42 4AD "H4'" H4* H 0 1 N N N -3.236 5.607 39.050 -0.814 -2.172 1.688 "H4'" 4AD 43 4AD "H3'" H3* H 0 1 N N N -1.294 7.980 39.186 -1.657 -3.372 -0.835 "H3'" 4AD 44 4AD H2 H2 H 0 1 N N N -0.578 5.378 38.616 -3.098 -4.441 0.625 H2 4AD 45 4AD "H2'" H2* H 0 1 N N N -0.753 7.607 36.810 -3.271 -1.735 -1.337 "H2'" 4AD 46 4AD H1 H1 H 0 1 N N N -1.498 5.660 35.820 -4.583 -3.430 -0.533 H1 4AD 47 4AD "H1'" H1* H 0 1 N N N -3.332 7.034 35.971 -3.388 -0.968 1.634 "H1'" 4AD 48 4AD H3 H3 H 0 1 N N N -3.171 9.206 31.954 -7.940 0.552 1.747 H3 4AD 49 4AD HN61 1HN6 H 0 0 N N N -2.892 13.589 35.063 -6.037 4.143 -1.621 HN61 4AD 50 4AD HN62 2HN6 H 0 0 N N N -3.000 13.367 33.302 -7.593 4.183 -0.990 HN62 4AD 51 4AD H8 H8 H 0 1 N N N -2.788 9.871 38.572 -2.179 1.264 -1.201 H8 4AD 52 # # 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 4AD O2P P DOUB N N 1 4AD P O1P SING N N 2 4AD P O3P SING N N 3 4AD P "O5'" SING N N 4 4AD O1P HOP1 SING N N 5 4AD O3P C SING N N 6 4AD C O DOUB N N 7 4AD C CA SING N N 8 4AD CA N SING N N 9 4AD CA CB SING N N 10 4AD CA HA SING N N 11 4AD N HN1 SING N N 12 4AD N HN2 SING N N 13 4AD N HN3 SING N N 14 4AD CB CG SING N N 15 4AD CB HB1 SING N N 16 4AD CB HB2 SING N N 17 4AD CG OD1 DOUB N N 18 4AD CG ND2 SING N N 19 4AD ND2 HD21 SING N N 20 4AD ND2 HD22 SING N N 21 4AD "O5'" "C5'" SING N N 22 4AD "C5'" "C4'" SING N N 23 4AD "C5'" "H5'1" SING N N 24 4AD "C5'" "H5'2" SING N N 25 4AD "C4'" "C3'" SING N N 26 4AD "C4'" "O4'" SING N N 27 4AD "C4'" "H4'" SING N N 28 4AD "C3'" "O3'" SING N N 29 4AD "C3'" "C2'" SING N N 30 4AD "C3'" "H3'" SING N N 31 4AD "O3'" H2 SING N N 32 4AD "C2'" "O2'" SING N N 33 4AD "C2'" "C1'" SING N N 34 4AD "C2'" "H2'" SING N N 35 4AD "O2'" H1 SING N N 36 4AD "C1'" "O4'" SING N N 37 4AD "C1'" N9 SING N N 38 4AD "C1'" "H1'" SING N N 39 4AD N9 C4 SING Y N 40 4AD N9 C8 SING Y N 41 4AD C4 N3 SING Y N 42 4AD C4 C5 DOUB Y N 43 4AD N3 C2 DOUB Y N 44 4AD C2 N1 SING Y N 45 4AD C2 H3 SING N N 46 4AD N1 C6 DOUB Y N 47 4AD C6 N6 SING N N 48 4AD C6 C5 SING Y N 49 4AD N6 HN61 SING N N 50 4AD N6 HN62 SING N N 51 4AD C5 N7 SING Y N 52 4AD N7 C8 DOUB Y N 53 4AD C8 H8 SING N N 54 # # 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 4AD SMILES ACDLabs 10.04 "O=C(N)CC(C(=O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)[NH3+]" 4AD SMILES_CANONICAL CACTVS 3.341 "NC(=O)C[C@H]([NH3+])C(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23" 4AD SMILES CACTVS 3.341 "NC(=O)C[CH]([NH3+])C(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23" 4AD 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)[C@H](CC(=O)N)[NH3+])O)O)N" 4AD SMILES "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC(=O)C(CC(=O)N)[NH3+])O)O)N" 4AD InChI InChI 1.03 "InChI=1S/C14H20N7O9P/c15-5(1-7(16)22)14(25)30-31(26,27)28-2-6-9(23)10(24)13(29-6)21-4-20-8-11(17)18-3-19-12(8)21/h3-6,9-10,13,23-24H,1-2,15H2,(H2,16,22)(H,26,27)(H2,17,18,19)/p+1/t5-,6+,9+,10+,13+/m0/s1" 4AD InChIKey InChI 1.03 BZHVCXQAFQWXPZ-VWJPMABRSA-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 4AD "SYSTEMATIC NAME" ACDLabs 10.04 "5'-O-[(R)-{[(2S)-4-amino-2-ammonio-4-oxobutanoyl]oxy}(hydroxy)phosphoryl]adenosine" 4AD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S)-4-amino-1-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-1,4-dioxo-butan-2-yl]azanium" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 4AD "Create component" 2005-05-20 RCSB 4AD "Modify descriptor" 2011-06-04 RCSB 4AD "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 4AD _pdbx_chem_comp_synonyms.name ASNAMP _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##