data_MCA # _chem_comp.id MCA _chem_comp.name "METHYLMALONYL-COENZYME A" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H40 N7 O19 P3 S" _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 867.607 _chem_comp.one_letter_code ? _chem_comp.three_letter_code MCA _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 4REQ _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 MCA C8 C8 C 0 1 Y N N -26.863 111.879 41.927 -2.619 0.735 -8.412 C8 MCA 1 MCA N9 N9 N 0 1 Y N N -28.085 112.488 42.023 -2.210 -0.470 -8.898 N9 MCA 2 MCA C4 C4 C 0 1 Y N N -28.267 113.137 40.825 -3.078 -0.825 -9.899 C4 MCA 3 MCA C5 C5 C 0 1 Y N N -27.130 112.887 40.077 -4.022 0.212 -9.980 C5 MCA 4 MCA N7 N7 N 0 1 Y N N -26.247 112.085 40.782 -3.682 1.134 -9.048 N7 MCA 5 MCA N3 N3 N 0 1 Y N N -29.336 113.879 40.461 -3.194 -1.868 -10.714 N3 MCA 6 MCA C2 C2 C 0 1 Y N N -29.162 114.365 39.231 -4.171 -1.927 -11.594 C2 MCA 7 MCA N1 N1 N 0 1 Y N N -28.124 114.194 38.413 -5.078 -0.974 -11.711 N1 MCA 8 MCA C6 C6 C 0 1 Y N N -27.063 113.455 38.792 -5.047 0.103 -10.935 C6 MCA 9 MCA N6 N6 N 0 1 N N N -26.047 113.313 37.939 -6.001 1.097 -11.065 N6 MCA 10 MCA "C1'" "C1'" C 0 1 N N R -29.025 112.449 43.148 -1.052 -1.242 -8.440 "C1'" MCA 11 MCA "C2'" "C2'" C 0 1 N N R -29.732 111.084 43.170 0.237 -0.778 -9.164 "C2'" MCA 12 MCA "O2'" "O2'" O 0 1 N N N -30.901 111.104 42.384 0.397 -1.461 -10.409 "O2'" MCA 13 MCA "C3'" "C3'" C 0 1 N N S -30.027 110.913 44.654 1.342 -1.195 -8.158 "C3'" MCA 14 MCA "O3'" "O3'" O 0 1 N N N -31.165 111.723 44.953 1.920 -2.445 -8.540 "O3'" MCA 15 MCA "C4'" "C4'" C 0 1 N N R -28.762 111.474 45.285 0.596 -1.326 -6.816 "C4'" MCA 16 MCA "O4'" "O4'" O 0 1 N N N -28.340 112.546 44.382 -0.775 -0.967 -7.050 "O4'" MCA 17 MCA "C5'" "C5'" C 0 1 N N N -27.630 110.494 45.490 1.212 -0.380 -5.784 "C5'" MCA 18 MCA "O5'" "O5'" O 0 1 N N N -27.270 109.817 44.250 0.510 -0.503 -4.546 "O5'" MCA 19 MCA P1 P1 P 0 1 N N S -27.474 108.227 44.197 1.208 0.514 -3.511 P1 MCA 20 MCA O11 O11 O 0 1 N N N -27.087 107.694 42.902 1.110 1.894 -4.036 O11 MCA 21 MCA O12 O12 O 0 1 N N N -28.818 107.988 44.766 2.758 0.117 -3.331 O12 MCA 22 MCA O6 O6 O 0 1 N N N -26.391 107.801 45.312 0.462 0.427 -2.087 O6 MCA 23 MCA P2 P2 P 0 1 N N R -26.529 107.121 46.762 1.208 1.465 -1.108 P2 MCA 24 MCA O21 O21 O 0 1 N N N -27.534 107.828 47.551 1.110 2.830 -1.669 O21 MCA 25 MCA O22 O22 O 0 1 N N N -25.147 106.845 47.211 2.757 1.052 -0.967 O22 MCA 26 MCA O7 O7 O 0 1 N N N -27.219 105.745 46.366 0.510 1.430 0.342 O7 MCA 27 MCA CPB CPB C 0 1 N N N -26.536 104.716 45.617 1.212 2.366 1.161 CPB MCA 28 MCA CPA CPA C 0 1 N N N -27.471 103.508 45.437 0.595 2.382 2.561 CPA MCA 29 MCA CP7 CP7 C 0 1 N N R -27.498 102.671 46.728 1.348 3.385 3.438 CP7 MCA 30 MCA CP9 CP9 C 0 1 N N N -26.965 102.640 44.317 0.698 0.987 3.180 CP9 MCA 31 MCA CP8 CP8 C 0 1 N N N -28.903 103.951 45.084 -0.875 2.791 2.466 CP8 MCA 32 MCA OP3 OP3 O 0 1 N N N -27.981 101.352 46.414 1.351 4.665 2.803 OP3 MCA 33 MCA CP6 CP6 C 0 1 N N N -26.206 102.430 47.484 0.666 3.491 4.778 CP6 MCA 34 MCA OP2 OP2 O 0 1 N N N -25.554 103.338 48.009 0.005 4.472 5.046 OP2 MCA 35 MCA NP2 NP2 N 0 1 N N N -25.833 101.165 47.562 0.791 2.496 5.678 NP2 MCA 36 MCA CP5 CP5 C 0 1 N N N -24.631 100.755 48.281 0.112 2.590 6.973 CP5 MCA 37 MCA CP4 CP4 C 0 1 N N N -24.659 99.309 48.682 0.416 1.339 7.800 CP4 MCA 38 MCA CP3 CP3 C 0 1 N N N -23.487 98.844 49.500 -0.281 1.436 9.132 CP3 MCA 39 MCA OP1 OP1 O 0 1 N N N -22.694 99.630 50.080 -0.956 2.409 9.394 OP1 MCA 40 MCA NP1 NP1 N 0 1 N N N -23.333 97.528 49.584 -0.156 0.441 10.033 NP1 MCA 41 MCA CP2 CP2 C 0 1 N N N -22.176 97.076 50.402 -0.835 0.535 11.327 CP2 MCA 42 MCA CP1 CP1 C 0 1 N N N -22.063 95.589 50.145 -0.531 -0.715 12.155 CP1 MCA 43 MCA P3 P3 P 0 1 N N N -32.648 111.150 45.224 3.495 -2.185 -8.749 P3 MCA 44 MCA O31 O31 O 0 1 N N N -33.208 110.563 43.975 4.087 -1.698 -7.483 O31 MCA 45 MCA O32 O32 O 0 1 N N N -33.446 112.318 45.742 4.213 -3.559 -9.184 O32 MCA 46 MCA O33 O33 O 0 1 N N N -32.493 110.094 46.304 3.708 -1.081 -9.901 O33 MCA 47 MCA S S S 0 1 N N N -20.550 94.796 50.662 -1.370 -0.599 13.754 S MCA 48 MCA CS1 CS1 C 0 1 N N N -21.076 93.114 50.521 -0.876 -2.080 14.457 CS1 MCA 49 MCA OS1 OS1 O 0 1 N N N -22.116 92.706 50.100 -0.153 -2.834 13.839 OS1 MCA 50 MCA CS2 CS2 C 0 1 N N R -20.024 92.187 51.003 -1.339 -2.448 15.843 CS2 MCA 51 MCA CS3 CS3 C 0 1 N N N -19.248 91.676 49.816 -0.861 -1.389 16.838 CS3 MCA 52 MCA CS4 CS4 C 0 1 N N N -20.480 90.974 51.780 -0.768 -3.790 16.224 CS4 MCA 53 MCA OS4 OS4 O 0 1 N N N -20.373 90.893 52.984 -1.049 -4.322 17.424 OS4 MCA 54 MCA OS5 OS5 O 0 1 N N N -20.942 90.090 51.051 -0.058 -4.386 15.449 OS5 MCA 55 MCA H8 H8 H 0 1 N N N -26.405 111.263 42.719 -2.132 1.280 -7.616 H8 MCA 56 MCA H2 H2 H 0 1 N N N -29.982 114.989 38.839 -4.234 -2.787 -12.245 H2 MCA 57 MCA HN61 1HN6 H 0 0 N N N -25.998 113.724 37.007 -6.704 1.011 -11.729 HN61 MCA 58 MCA HN62 2HN6 H 0 0 N N N -25.901 112.310 37.823 -5.967 1.880 -10.493 HN62 MCA 59 MCA "H1'" "H1'" H 0 1 N N N -29.737 113.297 43.020 -1.217 -2.308 -8.596 "H1'" MCA 60 MCA "H2'" "H2'" H 0 1 N N N -29.133 110.245 42.742 0.233 0.301 -9.312 "H2'" MCA 61 MCA "HO2'" "'HO2" H 0 0 N N N -31.337 110.260 42.397 -0.367 -1.231 -10.954 "HO2'" MCA 62 MCA "H3'" "H3'" H 0 1 N N N -30.253 109.877 45.000 2.110 -0.425 -8.093 "H3'" MCA 63 MCA "H4'" "H4'" H 0 1 N N N -29.000 111.804 46.323 0.654 -2.354 -6.458 "H4'" MCA 64 MCA "H5'1" "1H5'" H 0 0 N N N -26.744 110.987 45.955 1.139 0.646 -6.143 "H5'1" MCA 65 MCA "H5'2" "2H5'" H 0 0 N N N -27.866 109.763 46.297 2.261 -0.639 -5.634 "H5'2" MCA 66 MCA HOC HOC H 0 1 N N N -28.938 107.046 44.734 2.776 -0.786 -2.988 HOC MCA 67 MCA HOM HOM H 0 1 N N N -25.228 106.443 48.067 2.776 0.158 -0.599 HOM MCA 68 MCA HPB1 1HPB H 0 0 N N N -26.142 105.093 44.644 1.139 3.361 0.721 HPB1 MCA 69 MCA HPB2 2HPB H 0 0 N N N -25.563 104.430 46.082 2.260 2.075 1.229 HPB2 MCA 70 MCA H7 H7 H 0 1 N N N -28.133 103.302 47.392 2.374 3.047 3.579 H7 MCA 71 MCA H91 1H9 H 0 1 N N N -27.642 101.764 44.186 1.745 0.749 3.369 H91 MCA 72 MCA H92 2H9 H 0 1 N N N -26.830 103.212 43.369 0.145 0.964 4.119 H92 MCA 73 MCA H93 3H9 H 0 1 N N N -25.904 102.331 44.470 0.277 0.253 2.492 H93 MCA 74 MCA H81 1H8 H 0 1 N N N -29.580 103.075 44.953 -0.948 3.785 2.025 H81 MCA 75 MCA H82 2H8 H 0 1 N N N -29.304 104.669 45.835 -1.411 2.077 1.841 H82 MCA 76 MCA H83 3H8 H 0 1 N N N -28.915 104.614 44.187 -1.314 2.803 3.463 H83 MCA 77 MCA HO3 HO3 H 0 1 N N N -27.997 100.835 47.211 0.426 4.927 2.698 HO3 MCA 78 MCA HN2 HN2 H 0 1 N N N -26.458 100.520 47.078 1.330 1.717 5.469 HN2 MCA 79 MCA H51 1H5 H 0 1 N N N -23.713 100.988 47.691 -0.963 2.668 6.815 H51 MCA 80 MCA H52 2H5 H 0 1 N N N -24.450 101.411 49.164 0.466 3.472 7.506 H52 MCA 81 MCA H41 1H4 H 0 1 N N N -25.611 99.078 49.213 1.492 1.261 7.959 H41 MCA 82 MCA H42 2H4 H 0 1 N N N -24.775 98.664 47.779 0.062 0.456 7.268 H42 MCA 83 MCA HN1 HN1 H 0 1 N N N -24.008 96.945 49.089 0.382 -0.337 9.823 HN1 MCA 84 MCA H21 1H2 H 0 1 N N N -21.235 97.640 50.201 -1.911 0.613 11.169 H21 MCA 85 MCA H22 2H2 H 0 1 N N N -22.257 97.340 51.482 -0.481 1.417 11.860 H22 MCA 86 MCA H11 1H1 H 0 1 N N N -22.934 95.064 50.601 0.544 -0.794 12.313 H11 MCA 87 MCA H12 2H1 H 0 1 N N N -22.242 95.382 49.064 -0.885 -1.598 11.622 H12 MCA 88 MCA HOW HOW H 0 1 N N N -34.319 111.980 45.901 5.152 -3.360 -9.298 HOW MCA 89 MCA HOX HOX H 0 1 N N N -33.366 109.756 46.463 3.309 -1.437 -10.707 HOX MCA 90 MCA HS2 HS2 H 0 1 N N N -19.430 92.804 51.717 -2.428 -2.498 15.861 HS2 MCA 91 MCA H31 1H3 H 0 1 N N N -18.456 90.978 50.178 0.227 -1.339 16.820 H31 MCA 92 MCA H32 2H3 H 0 1 N N N -19.905 91.210 49.045 -1.274 -0.419 16.563 H32 MCA 93 MCA H33 3H3 H 0 1 N N N -18.835 92.500 49.189 -1.196 -1.655 17.841 H33 MCA 94 MCA HO4 HO4 H 0 1 N N N -20.659 90.130 53.472 -0.682 -5.183 17.668 HO4 MCA 95 # 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 MCA C8 N9 SING Y N 1 MCA C8 N7 DOUB Y N 2 MCA C8 H8 SING N N 3 MCA N9 C4 SING Y N 4 MCA N9 "C1'" SING N N 5 MCA C4 C5 SING Y N 6 MCA C4 N3 DOUB Y N 7 MCA C5 N7 SING Y N 8 MCA C5 C6 DOUB Y N 9 MCA N3 C2 SING Y N 10 MCA C2 N1 DOUB Y N 11 MCA C2 H2 SING N N 12 MCA N1 C6 SING Y N 13 MCA C6 N6 SING N N 14 MCA N6 HN61 SING N N 15 MCA N6 HN62 SING N N 16 MCA "C1'" "C2'" SING N N 17 MCA "C1'" "O4'" SING N N 18 MCA "C1'" "H1'" SING N N 19 MCA "C2'" "O2'" SING N N 20 MCA "C2'" "C3'" SING N N 21 MCA "C2'" "H2'" SING N N 22 MCA "O2'" "HO2'" SING N N 23 MCA "C3'" "O3'" SING N N 24 MCA "C3'" "C4'" SING N N 25 MCA "C3'" "H3'" SING N N 26 MCA "O3'" P3 SING N N 27 MCA "C4'" "O4'" SING N N 28 MCA "C4'" "C5'" SING N N 29 MCA "C4'" "H4'" SING N N 30 MCA "C5'" "O5'" SING N N 31 MCA "C5'" "H5'1" SING N N 32 MCA "C5'" "H5'2" SING N N 33 MCA "O5'" P1 SING N N 34 MCA P1 O11 DOUB N N 35 MCA P1 O12 SING N N 36 MCA P1 O6 SING N N 37 MCA O12 HOC SING N N 38 MCA O6 P2 SING N N 39 MCA P2 O21 DOUB N N 40 MCA P2 O22 SING N N 41 MCA P2 O7 SING N N 42 MCA O22 HOM SING N N 43 MCA O7 CPB SING N N 44 MCA CPB CPA SING N N 45 MCA CPB HPB1 SING N N 46 MCA CPB HPB2 SING N N 47 MCA CPA CP7 SING N N 48 MCA CPA CP9 SING N N 49 MCA CPA CP8 SING N N 50 MCA CP7 OP3 SING N N 51 MCA CP7 CP6 SING N N 52 MCA CP7 H7 SING N N 53 MCA CP9 H91 SING N N 54 MCA CP9 H92 SING N N 55 MCA CP9 H93 SING N N 56 MCA CP8 H81 SING N N 57 MCA CP8 H82 SING N N 58 MCA CP8 H83 SING N N 59 MCA OP3 HO3 SING N N 60 MCA CP6 OP2 DOUB N N 61 MCA CP6 NP2 SING N N 62 MCA NP2 CP5 SING N N 63 MCA NP2 HN2 SING N N 64 MCA CP5 CP4 SING N N 65 MCA CP5 H51 SING N N 66 MCA CP5 H52 SING N N 67 MCA CP4 CP3 SING N N 68 MCA CP4 H41 SING N N 69 MCA CP4 H42 SING N N 70 MCA CP3 OP1 DOUB N N 71 MCA CP3 NP1 SING N N 72 MCA NP1 CP2 SING N N 73 MCA NP1 HN1 SING N N 74 MCA CP2 CP1 SING N N 75 MCA CP2 H21 SING N N 76 MCA CP2 H22 SING N N 77 MCA CP1 S SING N N 78 MCA CP1 H11 SING N N 79 MCA CP1 H12 SING N N 80 MCA P3 O31 DOUB N N 81 MCA P3 O32 SING N N 82 MCA P3 O33 SING N N 83 MCA O32 HOW SING N N 84 MCA O33 HOX SING N N 85 MCA S CS1 SING N N 86 MCA CS1 OS1 DOUB N N 87 MCA CS1 CS2 SING N N 88 MCA CS2 CS3 SING N N 89 MCA CS2 CS4 SING N N 90 MCA CS2 HS2 SING N N 91 MCA CS3 H31 SING N N 92 MCA CS3 H32 SING N N 93 MCA CS3 H33 SING N N 94 MCA CS4 OS4 SING N N 95 MCA CS4 OS5 DOUB N N 96 MCA OS4 HO4 SING N N 97 # 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 MCA SMILES ACDLabs 10.04 "O=C(O)C(C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3OP(=O)(O)O)C" MCA SMILES_CANONICAL CACTVS 3.341 "C[C@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23" MCA SMILES CACTVS 3.341 "C[CH](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[CH](O)C(C)(C)CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23" MCA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H](C(=O)O)C(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)CO[P@@](=O)(O)O[P@@](=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O" MCA SMILES "OpenEye OEToolkits" 1.5.0 "CC(C(=O)O)C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O" MCA InChI InChI 1.03 ;InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13-,16-,17-,18+,22-/m1/s1 ; MCA InChIKey InChI 1.03 MZFOKIKEPGUZEN-AGCMQPJKSA-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 MCA "SYSTEMATIC NAME" ACDLabs 10.04 ;(3S,5R,9R,20R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8,20-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphahenicosan-21-oic acid 3,5-dioxide (non-preferred name) ; MCA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-3-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethylsulfanyl]-2-methyl-3-oxo-propanoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site MCA "Create component" 1999-07-08 RCSB MCA "Modify descriptor" 2011-06-04 RCSB #