data_MCN
# 
_chem_comp.id                                    MCN 
_chem_comp.name                                  "PTERIN CYTOSINE DINUCLEOTIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H22 N8 O13 P2 S2" 
_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                    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                        696.501 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MCN 
_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        1DGJ 
_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 
MCN N1     N1    N 0 1 N N N 6.645  48.058 70.202 0.121  0.689  -7.872  N1     MCN 1  
MCN C2     C2    C 0 1 N N N 7.907  47.479 69.922 1.092  -0.242 -7.867  C2     MCN 2  
MCN N3     N3    N 0 1 N N N 7.923  46.109 69.717 2.155  -0.131 -8.661  N3     MCN 3  
MCN C4     C4    C 0 1 N N N 6.827  45.367 69.775 2.284  0.904  -9.480  C4     MCN 4  
MCN C5     C5    C 0 1 N N N 5.510  45.955 70.067 1.287  1.900  -9.505  C5     MCN 5  
MCN C6     C6    C 0 1 N N N 5.517  47.311 70.266 0.209  1.771  -8.697  C6     MCN 6  
MCN O2     O2    O 0 1 N N N 8.950  48.170 69.863 0.996  -1.203 -7.122  O2     MCN 7  
MCN N4     N4    N 0 1 N N N 6.798  44.025 69.578 3.388  1.008  -10.295 N4     MCN 8  
MCN "C1'"  C1*   C 0 1 N N R 6.604  49.510 70.428 -1.037 0.540  -6.988  "C1'"  MCN 9  
MCN C2D    C2*   C 0 1 N N R 5.785  50.258 69.342 -1.769 -0.787 -7.280  C2D    MCN 10 
MCN "O2'"  O2*   O 0 1 N N N 6.616  50.616 68.242 -2.901 -0.567 -8.125  "O2'"  MCN 11 
MCN "C3'"  C3*   C 0 1 N N S 5.262  51.475 70.077 -2.221 -1.280 -5.885  "C3'"  MCN 12 
MCN C4D    C4*   C 0 1 N N R 5.035  50.950 71.484 -1.711 -0.189 -4.918  C4D    MCN 13 
MCN O4D    O4*   O 0 1 N N N 5.862  49.753 71.635 -0.608 0.433  -5.612  O4D    MCN 14 
MCN "O3'"  O3*   O 0 1 N N N 6.301  52.466 70.174 -3.646 -1.376 -5.825  "O3'"  MCN 15 
MCN "C5'"  C5*   C 0 1 N N N 3.594  50.637 71.739 -1.229 -0.818 -3.609  "C5'"  MCN 16 
MCN "O5'"  O5*   O 0 1 N N N 3.047  49.831 70.514 -0.696 0.199  -2.760  "O5'"  MCN 17 
MCN PA     PA    P 0 1 N N S 1.560  49.320 70.490 -0.211 -0.528 -1.408  PA     MCN 18 
MCN O1A    O1A   O 0 1 N N N 1.342  48.327 71.601 0.822  -1.536 -1.735  O1A    MCN 19 
MCN O2A    O2A   O 0 1 N N N 1.253  48.754 69.046 -1.466 -1.255 -0.710  O2A    MCN 20 
MCN O3A    O3A   O 0 1 N N N 0.625  50.596 70.858 0.404  0.565  -0.400  O3A    MCN 21 
MCN PB     PB    P 0 1 N N S 0.307  51.972 70.090 0.866  -0.228 0.921   PB     MCN 22 
MCN O1B    O1B   O 0 1 N N N 1.433  52.447 69.317 -0.304 -0.901 1.527   O1B    MCN 23 
MCN O2B    O2B   O 0 1 N N N -1.069 51.770 69.472 1.973  -1.329 0.527   O2B    MCN 24 
MCN O3B    O3B   O 0 1 N N N 0.236  52.942 71.404 1.495  0.810  1.979   O3B    MCN 25 
MCN C10    C10   C 0 1 N N N -0.996 52.975 72.204 1.884  0.049  3.124   C10    MCN 26 
MCN "C9'"  "C9'" C 0 1 N N R -0.771 52.446 73.613 2.492  0.981  4.173   "C9'"  MCN 27 
MCN "C8'"  "C8'" C 0 1 N N N -2.029 52.717 74.329 2.919  0.168  5.368   "C8'"  MCN 28 
MCN "S8'"  "S8'" S 0 1 N N N -3.389 52.092 73.569 4.601  -0.311 5.582   "S8'"  MCN 29 
MCN "C7'"  "C7'" C 0 1 N N N -2.046 53.371 75.481 1.972  -0.183 6.272   "C7'"  MCN 30 
MCN "S7'"  "S7'" S 0 1 N N N -3.429 53.741 76.371 2.349  -1.139 7.704   "S7'"  MCN 31 
MCN "C6'"  "C6'" C 0 1 Y N N -0.806 53.763 76.262 0.601  0.287  5.978   "C6'"  MCN 32 
MCN C7     C7    C 0 1 Y N N 0.392  53.079 75.629 0.447  1.367  5.071   C7     MCN 33 
MCN "O9'"  "O9'" O 0 1 N N N 0.392  53.097 74.211 1.533  1.964  4.535   "O9'"  MCN 34 
MCN "N5'"  "N5'" N 0 1 Y N N -0.576 55.223 76.163 -0.447 -0.290 6.533   "N5'"  MCN 35 
MCN C4A    C4A   C 0 1 Y N N 0.753  55.621 76.518 -1.672 0.141  6.221   C4A    MCN 36 
MCN "N8'"  "N8'" N 0 1 Y N N 1.682  53.415 76.076 -0.761 1.791  4.757   "N8'"  MCN 37 
MCN C4B    C4B   C 0 1 Y N N 1.808  54.684 76.480 -1.834 1.208  5.304   C4B    MCN 38 
MCN "N1'"  "N1'" N 0 1 Y N N 3.082  55.037 76.818 -3.075 1.614  5.005   "N1'"  MCN 39 
MCN "C2'"  "C2'" C 0 1 Y N N 3.408  56.347 77.232 -4.123 1.032  5.558   "C2'"  MCN 40 
MCN "N2'"  "N2'" N 0 1 N N N 4.654  56.749 77.569 -5.387 1.481  5.221   "N2'"  MCN 41 
MCN "N3'"  "N3'" N 0 1 Y N N 2.347  57.316 77.282 -4.013 0.030  6.426   "N3'"  MCN 42 
MCN "C4'"  "C4'" C 0 1 Y N N 1.071  56.971 76.961 -2.831 -0.443 6.784   "C4'"  MCN 43 
MCN "O4'"  "O4'" O 0 1 N N N 0.179  57.879 77.041 -2.732 -1.463 7.668   "O4'"  MCN 44 
MCN H5     H5    H 0 1 N N N 4.557  45.402 70.133 1.378  2.749  -10.167 H5     MCN 45 
MCN H6     H6    H 0 1 N N N 4.567  47.826 70.488 -0.569 2.518  -8.701  H6     MCN 46 
MCN HN41   1HN4  H 0 0 N N N 5.954  43.453 69.622 4.074  0.323  -10.272 HN41   MCN 47 
MCN HN42   2HN4  H 0 0 N N N 7.468  43.615 70.227 3.477  1.764  -10.895 HN42   MCN 48 
MCN "H1'"  H1*   H 0 1 N N N 7.662  49.860 70.442 -1.717 1.383  -7.108  "H1'"  MCN 49 
MCN "H2'"  H2*   H 0 1 N N N 4.965  49.644 68.900 -1.088 -1.505 -7.736  "H2'"  MCN 50 
MCN "HO2'" *HO2  H 0 0 N N N 6.114  51.073 67.577 -3.349 -1.418 -8.220  "HO2'" MCN 51 
MCN "H3'"  H3*   H 0 1 N N N 4.368  51.923 69.582 -1.765 -2.242 -5.652  "H3'"  MCN 52 
MCN "H4'"  H4*   H 0 1 N N N 5.318  51.729 72.229 -2.496 0.540  -4.721  "H4'"  MCN 53 
MCN "HO3'" *HO3  H 0 0 N N N 5.973  53.229 70.634 -3.906 -2.069 -6.447  "HO3'" MCN 54 
MCN "H5'1" 1H5*  H 0 0 N N N 3.432  50.109 72.708 -2.067 -1.305 -3.110  "H5'1" MCN 55 
MCN "H5'2" 2H5*  H 0 0 N N N 2.988  51.546 71.960 -0.455 -1.555 -3.823  "H5'2" MCN 56 
MCN HOA2   2HOA  H 0 0 N N N 0.354  48.445 69.031 -2.115 -0.565 -0.514  HOA2   MCN 57 
MCN HOB2   2HOB  H 0 0 N N N -1.256 52.583 69.018 2.717  -0.850 0.137   HOB2   MCN 58 
MCN H101   1H10  H 0 0 N N N -1.441 53.997 72.220 1.009  -0.448 3.544   H101   MCN 59 
MCN H102   2H10  H 0 0 N N N -1.825 52.431 71.694 2.621  -0.698 2.830   H102   MCN 60 
MCN "H9'"  "H9'" H 0 1 N N N -0.541 51.355 73.646 3.366  1.475  3.747   "H9'"  MCN 61 
MCN HS8    HS8   H 0 1 N N N -4.200 52.266 74.030 4.499  -1.026 6.793   HS8    MCN 62 
MCN HS7    HS7   H 0 1 N N N -3.441 54.210 77.197 1.127  -1.219 8.260   HS7    MCN 63 
MCN HN21   1HN2  H 0 0 N N N 4.889  57.695 77.868 -6.170 1.067  5.616   HN21   MCN 64 
MCN HN22   2HN2  H 0 0 N N N 5.262  56.524 76.782 -5.489 2.211  4.590   HN22   MCN 65 
MCN HO4    HO4   H 0 1 N N N 0.386  58.759 77.330 -2.743 -2.281 7.153   HO4    MCN 66 
# 
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 
MCN N1    C2     SING N N 1  
MCN N1    C6     SING N N 2  
MCN N1    "C1'"  SING N N 3  
MCN C2    N3     SING N N 4  
MCN C2    O2     DOUB N N 5  
MCN N3    C4     DOUB N N 6  
MCN C4    C5     SING N N 7  
MCN C4    N4     SING N N 8  
MCN C5    C6     DOUB N N 9  
MCN C5    H5     SING N N 10 
MCN C6    H6     SING N N 11 
MCN N4    HN41   SING N N 12 
MCN N4    HN42   SING N N 13 
MCN "C1'" C2D    SING N N 14 
MCN "C1'" O4D    SING N N 15 
MCN "C1'" "H1'"  SING N N 16 
MCN C2D   "O2'"  SING N N 17 
MCN C2D   "C3'"  SING N N 18 
MCN C2D   "H2'"  SING N N 19 
MCN "O2'" "HO2'" SING N N 20 
MCN "C3'" C4D    SING N N 21 
MCN "C3'" "O3'"  SING N N 22 
MCN "C3'" "H3'"  SING N N 23 
MCN C4D   O4D    SING N N 24 
MCN C4D   "C5'"  SING N N 25 
MCN C4D   "H4'"  SING N N 26 
MCN "O3'" "HO3'" SING N N 27 
MCN "C5'" "O5'"  SING N N 28 
MCN "C5'" "H5'1" SING N N 29 
MCN "C5'" "H5'2" SING N N 30 
MCN "O5'" PA     SING N N 31 
MCN PA    O1A    DOUB N N 32 
MCN PA    O2A    SING N N 33 
MCN PA    O3A    SING N N 34 
MCN O2A   HOA2   SING N N 35 
MCN O3A   PB     SING N N 36 
MCN PB    O1B    DOUB N N 37 
MCN PB    O2B    SING N N 38 
MCN PB    O3B    SING N N 39 
MCN O2B   HOB2   SING N N 40 
MCN O3B   C10    SING N N 41 
MCN C10   "C9'"  SING N N 42 
MCN C10   H101   SING N N 43 
MCN C10   H102   SING N N 44 
MCN "C9'" "C8'"  SING N N 45 
MCN "C9'" "O9'"  SING N N 46 
MCN "C9'" "H9'"  SING N N 47 
MCN "C8'" "S8'"  SING N N 48 
MCN "C8'" "C7'"  DOUB N N 49 
MCN "S8'" HS8    SING N N 50 
MCN "C7'" "S7'"  SING N N 51 
MCN "C7'" "C6'"  SING N N 52 
MCN "S7'" HS7    SING N N 53 
MCN "C6'" C7     SING Y N 54 
MCN "C6'" "N5'"  DOUB Y N 55 
MCN C7    "O9'"  SING N N 56 
MCN C7    "N8'"  DOUB Y N 57 
MCN "N5'" C4A    SING Y N 58 
MCN C4A   C4B    SING Y N 59 
MCN C4A   "C4'"  DOUB Y N 60 
MCN "N8'" C4B    SING Y N 61 
MCN C4B   "N1'"  DOUB Y N 62 
MCN "N1'" "C2'"  SING Y N 63 
MCN "C2'" "N2'"  SING N N 64 
MCN "C2'" "N3'"  DOUB Y N 65 
MCN "N2'" HN21   SING N N 66 
MCN "N2'" HN22   SING N N 67 
MCN "N3'" "C4'"  SING Y N 68 
MCN "C4'" "O4'"  SING N N 69 
MCN "O4'" HO4    SING N N 70 
# 
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 
MCN SMILES           ACDLabs              10.04 O=P(O)(OCC1Oc2nc3nc(nc(O)c3nc2C(S)=C1S)N)OP(=O)(O)OCC5OC(N4C(=O)N=C(N)C=C4)C(O)C5O 
MCN InChI            InChI                1.02b 
;InChI=1/C19H22N8O13P2S2/c20-7-1-2-27(19(31)22-7)17-11(29)10(28)5(39-17)3-36-41(32,33)40-42(34,35)37-4-6-12(43)13(44)8-16(38-6)24-14-9(23-8)15(30)26-18(21)25-14/h1-2,5-6,10-11,17,28-29,43-44H,3-4H2,(H,32,33)(H,34,35)(H2,20,22,31)(H3,21,24,25,26,30)/t5-,6-,10-,11-,17-/m1/s1/f/h30,32,34H,20-21H2
;
MCN InChIKey         InChI                1.02b RBWYFPNWTRZKKZ-LQYLAPPJDQ 
MCN SMILES_CANONICAL CACTVS               3.341 NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]3Oc4nc5nc(N)nc(O)c5nc4C(=C3S)S)[C@@H](O)[C@H]2O 
MCN SMILES           CACTVS               3.341 NC1=NC(=O)N(C=C1)[CH]2O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]3Oc4nc5nc(N)nc(O)c5nc4C(=C3S)S)[CH](O)[CH]2O 
MCN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]3C(=C(c4c(nc5c(n4)c(nc(n5)N)O)O3)S)S)O)O 
MCN SMILES           "OpenEye OEToolkits" 1.5.0 C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OCC3C(=C(c4c(nc5c(n4)c(nc(n5)N)O)O3)S)S)O)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 
MCN "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(S)-{[(8R)-2-amino-4-hydroxy-6,7-disulfanyl-8H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine"                                                      
MCN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(8R)-2-amino-4-hydroxy-6,7-bis-sulfanyl-8H-pyrano[5,6-g]pteridin-8-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl hydrogen phosphate" 
# 
