data_HAM # _chem_comp.id HAM _chem_comp.name "HISTIDYL-ADENOSINE MONOPHOSPHATE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C16 H21 N8 O8 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2011-06-04 _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 484.361 _chem_comp.one_letter_code ? _chem_comp.three_letter_code HAM _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 1KMM _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 HAM P P P 0 1 N N N 13.859 -22.140 -13.896 -2.115 -1.879 0.316 P HAM 1 HAM O1P O1P O 0 1 N N N 14.615 -23.350 -13.483 -2.474 -3.363 0.079 O1P HAM 2 HAM O2P O2P O -1 1 N N N 13.013 -21.482 -12.883 -1.912 -1.633 1.828 O2P HAM 3 HAM O3P O3P O 0 1 N N N 12.952 -22.491 -15.255 -3.311 -0.945 -0.223 O3P HAM 4 HAM "O5'" O5* O 0 1 N N N 14.952 -21.062 -14.356 -0.758 -1.522 -0.473 "O5'" HAM 5 HAM "C5'" C5* C 0 1 N N N 15.606 -21.152 -15.629 0.284 -2.294 0.127 "C5'" HAM 6 HAM "C4'" C4* C 0 1 N N R 17.031 -20.672 -15.522 1.608 -2.001 -0.580 "C4'" HAM 7 HAM "O4'" O4* O 0 1 N N N 17.024 -19.271 -15.149 2.013 -0.635 -0.343 "O4'" HAM 8 HAM "C3'" C3* C 0 1 N N S 17.847 -21.363 -14.441 2.743 -2.860 0.020 "C3'" HAM 9 HAM "O3'" O3* O 0 1 N N N 18.451 -22.549 -14.952 2.979 -4.014 -0.789 "O3'" HAM 10 HAM "C2'" C2* C 0 1 N N R 18.875 -20.301 -14.058 3.974 -1.923 0.002 "C2'" HAM 11 HAM "O2'" O2* O 0 1 N N N 19.990 -20.248 -14.924 5.009 -2.472 -0.817 "O2'" HAM 12 HAM "C1'" C1* C 0 1 N N R 18.060 -19.016 -14.211 3.434 -0.609 -0.604 "C1'" HAM 13 HAM N9 N9 N 0 1 Y N N 17.447 -18.524 -12.979 4.051 0.547 0.050 N9 HAM 14 HAM C8 C8 C 0 1 Y N N 16.229 -18.878 -12.447 3.549 1.234 1.115 C8 HAM 15 HAM N7 N7 N 0 1 Y N N 15.928 -18.245 -11.338 4.356 2.203 1.439 N7 HAM 16 HAM C5 C5 C 0 1 Y N N 17.025 -17.423 -11.115 5.427 2.194 0.610 C5 HAM 17 HAM C6 C6 C 0 1 Y N N 17.319 -16.490 -10.099 6.582 2.984 0.479 C6 HAM 18 HAM N6 N6 N 0 1 N N N 16.517 -16.238 -9.070 6.815 4.044 1.337 N6 HAM 19 HAM N1 N1 N 0 1 Y N N 18.490 -15.822 -10.182 7.447 2.686 -0.485 N1 HAM 20 HAM C2 C2 C 0 1 Y N N 19.311 -16.085 -11.215 7.232 1.676 -1.309 C2 HAM 21 HAM N3 N3 N 0 1 Y N N 19.148 -16.941 -12.227 6.162 0.913 -1.227 N3 HAM 22 HAM C4 C4 C 0 1 Y N N 17.971 -17.585 -12.117 5.242 1.135 -0.295 C4 HAM 23 HAM C C C 0 1 N N N 12.442 -21.549 -16.022 -4.518 -0.995 0.362 C HAM 24 HAM O O O 0 1 N N N 12.471 -20.314 -15.802 -4.708 -1.742 1.293 O HAM 25 HAM CA CA C 0 1 N N S 11.582 -21.860 -17.307 -5.637 -0.121 -0.143 CA HAM 26 HAM N N N 1 1 N N N 10.830 -20.642 -17.745 -6.926 -0.671 0.298 N HAM 27 HAM CB CB C 0 1 N N N 12.416 -22.351 -18.504 -5.469 1.294 0.413 CB HAM 28 HAM CG CG C 0 1 Y N N 11.643 -22.460 -19.803 -6.515 2.197 -0.187 CG HAM 29 HAM CD2 CD2 C 0 1 Y N N 11.202 -21.474 -20.625 -7.394 2.955 0.496 CD2 HAM 30 HAM ND1 ND1 N 0 1 Y N N 11.399 -23.684 -20.407 -6.731 2.392 -1.497 ND1 HAM 31 HAM CE1 CE1 C 0 1 Y N N 10.826 -23.419 -21.570 -7.715 3.236 -1.650 CE1 HAM 32 HAM NE2 NE2 N 0 1 Y N N 10.685 -22.104 -21.758 -8.155 3.614 -0.431 NE2 HAM 33 HAM "H5'1" 1H5* H 0 0 N N N 15.545 -22.180 -16.055 0.049 -3.355 0.035 "H5'1" HAM 34 HAM "H5'2" 2H5* H 0 0 N N N 15.043 -20.609 -16.424 0.369 -2.032 1.181 "H5'2" HAM 35 HAM "H4'" H4* H 0 1 N N N 17.488 -20.886 -16.515 1.516 -2.189 -1.650 "H4'" HAM 36 HAM "H3'" H3* H 0 1 N N N 17.247 -21.703 -13.564 2.500 -3.154 1.041 "H3'" HAM 37 HAM "HO3'" *HO3 H 0 0 N N N 18.960 -22.980 -14.276 3.694 -4.510 -0.367 "HO3'" HAM 38 HAM "H2'" H2* H 0 1 N N N 19.311 -20.491 -13.049 4.339 -1.753 1.015 "H2'" HAM 39 HAM "HO2'" *HO2 H 0 0 N N N 20.570 -19.564 -14.599 5.260 -3.317 -0.420 "HO2'" HAM 40 HAM "H1'" H1* H 0 1 N N N 18.773 -18.224 -14.538 3.621 -0.581 -1.678 "H1'" HAM 41 HAM H8 H8 H 0 1 N N N 15.538 -19.620 -12.881 2.619 1.009 1.615 H8 HAM 42 HAM HN61 1HN6 H 0 0 N N N 15.635 -16.723 -8.987 7.618 4.580 1.239 HN61 HAM 43 HAM HN62 2HN6 H 0 0 N N N 16.777 -15.549 -8.378 6.174 4.255 2.034 HN62 HAM 44 HAM H2 H2 H 0 1 N N N 20.255 -15.515 -11.235 7.961 1.469 -2.078 H2 HAM 45 HAM HA HA H 0 1 N N N 10.889 -22.679 -17.004 -5.610 -0.089 -1.232 HA HAM 46 HAM HN1 1HN H 0 1 N N N 11.284 -19.813 -17.280 -7.675 -0.086 -0.039 HN1 HAM 47 HAM HN2 2HN H 0 1 N N N 9.853 -20.722 -17.434 -7.036 -1.605 -0.068 HN2 HAM 48 HAM HN3 3HN H 0 1 N N N 10.896 -20.549 -18.757 -6.951 -0.701 1.307 HN3 HAM 49 HAM HB1 1HB H 0 1 N N N 13.316 -21.707 -18.640 -5.585 1.275 1.497 HB1 HAM 50 HAM HB2 2HB H 0 1 N N N 12.909 -23.321 -18.262 -4.477 1.669 0.160 HB2 HAM 51 HAM HD2 HD2 H 0 1 N N N 11.252 -20.392 -20.416 -7.481 3.028 1.570 HD2 HAM 52 HAM HE1 HE1 H 0 1 N N N 10.507 -24.192 -22.288 -8.109 3.578 -2.596 HE1 HAM 53 HAM HE2 HE2 H 0 1 N N N 10.292 -21.665 -22.542 -8.876 4.236 -0.247 HE2 HAM 54 # 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 HAM P O1P DOUB N N 1 HAM P O2P SING N N 2 HAM P O3P SING N N 3 HAM P "O5'" SING N N 4 HAM O3P C SING N N 5 HAM "O5'" "C5'" SING N N 6 HAM "C5'" "C4'" SING N N 7 HAM "C5'" "H5'1" SING N N 8 HAM "C5'" "H5'2" SING N N 9 HAM "C4'" "O4'" SING N N 10 HAM "C4'" "C3'" SING N N 11 HAM "C4'" "H4'" SING N N 12 HAM "O4'" "C1'" SING N N 13 HAM "C3'" "O3'" SING N N 14 HAM "C3'" "C2'" SING N N 15 HAM "C3'" "H3'" SING N N 16 HAM "O3'" "HO3'" SING N N 17 HAM "C2'" "O2'" SING N N 18 HAM "C2'" "C1'" SING N N 19 HAM "C2'" "H2'" SING N N 20 HAM "O2'" "HO2'" SING N N 21 HAM "C1'" N9 SING N N 22 HAM "C1'" "H1'" SING N N 23 HAM N9 C8 SING Y N 24 HAM N9 C4 SING Y N 25 HAM C8 N7 DOUB Y N 26 HAM C8 H8 SING N N 27 HAM N7 C5 SING Y N 28 HAM C5 C6 SING Y N 29 HAM C5 C4 DOUB Y N 30 HAM C6 N6 SING N N 31 HAM C6 N1 DOUB Y N 32 HAM N6 HN61 SING N N 33 HAM N6 HN62 SING N N 34 HAM N1 C2 SING Y N 35 HAM C2 N3 DOUB Y N 36 HAM C2 H2 SING N N 37 HAM N3 C4 SING Y N 38 HAM C O DOUB N N 39 HAM C CA SING N N 40 HAM CA N SING N N 41 HAM CA CB SING N N 42 HAM CA HA SING N N 43 HAM N HN1 SING N N 44 HAM N HN2 SING N N 45 HAM N HN3 SING N N 46 HAM CB CG SING N N 47 HAM CB HB1 SING N N 48 HAM CB HB2 SING N N 49 HAM CG CD2 DOUB Y N 50 HAM CG ND1 SING Y N 51 HAM CD2 NE2 SING Y N 52 HAM CD2 HD2 SING N N 53 HAM ND1 CE1 DOUB Y N 54 HAM CE1 NE2 SING Y N 55 HAM CE1 HE1 SING N N 56 HAM NE2 HE2 SING N N 57 # 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 HAM SMILES ACDLabs 10.04 "[O-]P(=O)(OC(=O)C([NH3+])Cc1ncnc1)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4O" HAM SMILES_CANONICAL CACTVS 3.341 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P]([O-])(=O)OC(=O)[C@@H]([NH3+])Cc4c[nH]cn4)[C@@H](O)[C@H]3O" HAM SMILES CACTVS 3.341 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P]([O-])(=O)OC(=O)[CH]([NH3+])Cc4c[nH]cn4)[CH](O)[CH]3O" HAM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1c(nc[nH]1)C[C@@H](C(=O)O[P@](=O)([O-])OC[C@@H]2[C@H]([C@H]([C@@H](O2)n3cnc4c3ncnc4N)O)O)[NH3+]" HAM SMILES "OpenEye OEToolkits" 1.5.0 "c1c(nc[nH]1)CC(C(=O)OP(=O)([O-])OCC2C(C(C(O2)n3cnc4c3ncnc4N)O)O)[NH3+]" HAM InChI InChI 1.03 "InChI=1S/C16H21N8O8P/c17-8(1-7-2-19-4-20-7)16(27)32-33(28,29)30-3-9-11(25)12(26)15(31-9)24-6-23-10-13(18)21-5-22-14(10)24/h2,4-6,8-9,11-12,15,25-26H,1,3,17H2,(H,19,20)(H,28,29)(H2,18,21,22)/t8-,9+,11+,12+,15+/m0/s1" HAM InChIKey InChI 1.03 XTFBSLZFYLGYAT-OPYVMVOTSA-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 HAM "SYSTEMATIC NAME" ACDLabs 10.04 "5'-O-({[(2S)-2-ammonio-3-(1H-imidazol-4-yl)propanoyl]oxy}phosphinato)adenosine" HAM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [(2S)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoyl] phosphate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site HAM "Create component" 1999-07-08 RCSB HAM "Modify descriptor" 2011-06-04 RCSB #