data_MIA
#

_chem_comp.id                                   MIA
_chem_comp.name                                 "2-METHYLTHIO-N6-ISOPENTENYL-ADENOSINE-5'-MONOPHOSPHATE"
_chem_comp.type                                 "RNA LINKING"
_chem_comp.pdbx_type                            ATOMN
_chem_comp.formula                              "C16 H24 N5 O7 P S"
_chem_comp.mon_nstd_parent_comp_id              A
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    1999-07-08
_chem_comp.pdbx_modified_date                   2019-06-13
_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                       461.430
_chem_comp.one_letter_code                      A
_chem_comp.three_letter_code                    MIA
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       1B23
_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
MIA  OP3     O3P     O  0  1  N  Y  N  28.273  43.169  -31.562   6.510  -2.754  -1.685  OP3     MIA   1  
MIA  P       P       P  0  1  N  N  N  27.665  43.645  -30.146   6.383  -1.827  -0.375  P       MIA   2  
MIA  OP1     O1P     O  0  1  N  N  N  28.001  42.610  -29.130   6.044  -2.668   0.794  OP1     MIA   3  
MIA  OP2     O2P     O  0  1  N  N  N  26.242  44.014  -30.375   7.783  -1.078  -0.109  OP2     MIA   4  
MIA  "O5'"   "O5'"   O  0  1  N  N  N  28.469  44.977  -29.789   5.224  -0.733  -0.603  "O5'"   MIA   5  
MIA  "C5'"   "C5'"   C  0  1  N  N  N  29.783  44.912  -29.203   4.797   0.173   0.417  "C5'"   MIA   6  
MIA  "C4'"   "C4'"   C  0  1  N  N  R  30.486  46.249  -29.309   3.686   1.071  -0.131  "C4'"   MIA   7  
MIA  "O4'"   "O4'"   O  0  1  N  N  N  30.537  46.647  -30.706   2.515   0.286  -0.409  "O4'"   MIA   8  
MIA  "C3'"   "C3'"   C  0  1  N  N  S  29.834  47.435  -28.613   3.293   2.122   0.926  "C3'"   MIA   9  
MIA  "O3'"   "O3'"   O  0  1  N  N  N  30.117  47.523  -27.221   3.511   3.442   0.424  "O3'"   MIA  10  
MIA  "C2'"   "C2'"   C  0  1  N  N  R  30.402  48.619  -29.385   1.784   1.874   1.164  "C2'"   MIA  11  
MIA  "O2'"   "O2'"   O  0  1  N  N  N  31.697  49.014  -28.973   1.076   3.111   1.280  "O2'"   MIA  12  
MIA  "C1'"   "C1'"   C  0  1  N  N  R  30.438  48.059  -30.804   1.371   1.120  -0.126  "C1'"   MIA  13  
MIA  N9      N9      N  0  1  Y  N  N  29.165  48.396  -31.428   0.181   0.300   0.114  N9      MIA  14  
MIA  C8      C8      C  0  1  Y  N  N  28.145  47.581  -31.863   0.167  -1.000   0.527  C8      MIA  15  
MIA  N7      N7      N  0  1  Y  N  N  27.092  48.236  -32.275  -1.061  -1.417   0.639  N7      MIA  16  
MIA  C5      C5      C  0  1  Y  N  N  27.433  49.556  -32.119  -1.910  -0.414   0.306  C5      MIA  17  
MIA  C6      C6      C  0  1  Y  N  N  26.736  50.727  -32.385  -3.309  -0.286   0.242  C6      MIA  18  
MIA  N6      N6      N  0  1  N  N  N  25.457  50.809  -32.838  -4.131  -1.350   0.567  N6      MIA  19  
MIA  N1      N1      N  0  1  Y  N  N  27.387  51.915  -32.138  -3.824   0.878  -0.136  N1      MIA  20  
MIA  C2      C2      C  0  1  Y  N  N  28.658  51.886  -31.641  -3.042   1.905  -0.449  C2      MIA  21  
MIA  N3      N3      N  0  1  Y  N  N  29.405  50.813  -31.372  -1.722   1.827  -0.403  N3      MIA  22  
MIA  C4      C4      C  0  1  Y  N  N  28.723  49.682  -31.625  -1.123   0.701  -0.029  C4      MIA  23  
MIA  S10     S10     S  0  1  N  N  N  29.436  53.434  -31.351  -3.788   3.423  -0.943  S10     MIA  24  
MIA  C11     C11     C  0  1  N  N  N  31.066  52.985  -30.692  -5.536   2.966  -0.827  C11     MIA  25  
MIA  C12     C12     C  0  1  N  N  N  24.884  52.233  -32.581  -5.587  -1.200   0.495  C12     MIA  26  
MIA  C13     C13     C  0  1  N  N  N  23.650  52.745  -33.358  -6.246  -2.494   0.896  C13     MIA  27  
MIA  C14     C14     C  0  1  N  N  N  23.528  54.128  -33.291  -7.088  -3.080   0.081  C14     MIA  28  
MIA  C15     C15     C  0  1  N  N  N  22.852  55.030  -34.243  -7.505  -2.393  -1.194  C15     MIA  29  
MIA  C16     C16     C  0  1  N  N  N  24.529  54.909  -32.423  -7.639  -4.441   0.418  C16     MIA  30  
MIA  HOP3    HOP3    H  0  0  N  Y  N  28.715  42.335  -31.453   7.191  -3.438  -1.618  HOP3    MIA  31  
MIA  HOP2    HOP2    H  0  0  N  N  N  25.685  43.503  -29.799   8.068  -0.507  -0.836  HOP2    MIA  32  
MIA  "H5'"   "H5'1"  H  0  1  N  N  N  29.691  44.636  -28.142   4.420  -0.392   1.270  "H5'"   MIA  33  
MIA  "H5''"  "H5'2"  H  0  0  N  N  N  30.376  44.150  -29.730   5.640   0.788   0.733  "H5''"  MIA  34  
MIA  "H4'"   "H4'"   H  0  1  N  N  N  31.510  46.138  -28.923   4.025   1.566  -1.041  "H4'"   MIA  35  
MIA  "H3'"   "H3'"   H  0  1  N  N  N  28.747  47.391  -28.778   3.857   1.967   1.846  "H3'"   MIA  36  
MIA  "HO3'"  H3T     H  0  0  N  Y  N  29.679  48.283  -26.856   3.280   4.143   1.048  "HO3'"  MIA  37  
MIA  "H2'"   "H2'"   H  0  1  N  N  N  29.697  49.462  -29.339   1.625   1.253   2.046  "H2'"   MIA  38  
MIA  "HO2'"  "HO'2"  H  0  0  N  N  N  31.984  49.753  -29.496   1.364   3.660   2.022  "HO2'"  MIA  39  
MIA  "H1'"   "H1'"   H  0  1  N  N  N  31.282  48.491  -31.362   1.197   1.822  -0.942  "H1'"   MIA  40  
MIA  H8      H8      H  0  1  N  N  N  28.209  46.503  -31.864   1.044  -1.596   0.730  H8      MIA  41  
MIA  HN6     HN6     H  0  1  N  N  N  25.442  50.619  -33.820  -3.744  -2.196   0.842  HN6     MIA  42  
MIA  H111    H111    H  0  0  N  N  N  31.639  53.899  -30.475  -5.767   2.672   0.196  H111    MIA  43  
MIA  H112    H112    H  0  0  N  N  N  30.940  52.403  -29.767  -6.154   3.819  -1.108  H112    MIA  44  
MIA  H113    H113    H  0  0  N  N  N  31.608  52.380  -31.434  -5.739   2.133  -1.500  H113    MIA  45  
MIA  H121    H121    H  0  0  N  N  N  24.622  52.277  -31.514  -5.904  -0.406   1.171  H121    MIA  46  
MIA  H122    H122    H  0  0  N  N  N  25.700  52.941  -32.788  -5.876  -0.945  -0.525  H122    MIA  47  
MIA  H131    H131    H  0  0  N  N  N  22.963  52.104  -33.890  -6.024  -2.939   1.855  H131    MIA  48  
MIA  H151    H151    H  0  0  N  N  N  22.941  56.068  -33.891  -6.771  -2.597  -1.974  H151    MIA  49  
MIA  H152    H152    H  0  0  N  N  N  23.322  54.937  -35.233  -8.480  -2.766  -1.506  H152    MIA  50  
MIA  H153    H153    H  0  0  N  N  N  21.789  54.757  -34.315  -7.565  -1.318  -1.025  H153    MIA  51  
MIA  H161    H161    H  0  0  N  N  N  24.300  55.984  -32.475  -8.180  -4.390   1.363  H161    MIA  52  
MIA  H162    H162    H  0  0  N  N  N  24.453  54.568  -31.380  -8.318  -4.764  -0.371  H162    MIA  53  
MIA  H163    H163    H  0  0  N  N  N  25.550  54.733  -32.793  -6.819  -5.154   0.507  H163    MIA  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
MIA  OP3    P       SING  N  N   1  
MIA  OP3    HOP3    SING  N  N   2  
MIA  P      OP1     DOUB  N  N   3  
MIA  P      OP2     SING  N  N   4  
MIA  P      "O5'"   SING  N  N   5  
MIA  OP2    HOP2    SING  N  N   6  
MIA  "O5'"  "C5'"   SING  N  N   7  
MIA  "C5'"  "C4'"   SING  N  N   8  
MIA  "C5'"  "H5'"   SING  N  N   9  
MIA  "C5'"  "H5''"  SING  N  N  10  
MIA  "C4'"  "O4'"   SING  N  N  11  
MIA  "C4'"  "C3'"   SING  N  N  12  
MIA  "C4'"  "H4'"   SING  N  N  13  
MIA  "O4'"  "C1'"   SING  N  N  14  
MIA  "C3'"  "O3'"   SING  N  N  15  
MIA  "C3'"  "C2'"   SING  N  N  16  
MIA  "C3'"  "H3'"   SING  N  N  17  
MIA  "O3'"  "HO3'"  SING  N  N  18  
MIA  "C2'"  "O2'"   SING  N  N  19  
MIA  "C2'"  "C1'"   SING  N  N  20  
MIA  "C2'"  "H2'"   SING  N  N  21  
MIA  "O2'"  "HO2'"  SING  N  N  22  
MIA  "C1'"  N9      SING  N  N  23  
MIA  "C1'"  "H1'"   SING  N  N  24  
MIA  N9     C8      SING  Y  N  25  
MIA  N9     C4      SING  Y  N  26  
MIA  C8     N7      DOUB  Y  N  27  
MIA  C8     H8      SING  N  N  28  
MIA  N7     C5      SING  Y  N  29  
MIA  C5     C6      SING  Y  N  30  
MIA  C5     C4      DOUB  Y  N  31  
MIA  C6     N6      SING  N  N  32  
MIA  C6     N1      DOUB  Y  N  33  
MIA  N6     C12     SING  N  N  34  
MIA  N6     HN6     SING  N  N  35  
MIA  N1     C2      SING  Y  N  36  
MIA  C2     N3      DOUB  Y  N  37  
MIA  C2     S10     SING  N  N  38  
MIA  N3     C4      SING  Y  N  39  
MIA  S10    C11     SING  N  N  40  
MIA  C11    H111    SING  N  N  41  
MIA  C11    H112    SING  N  N  42  
MIA  C11    H113    SING  N  N  43  
MIA  C12    C13     SING  N  N  44  
MIA  C12    H121    SING  N  N  45  
MIA  C12    H122    SING  N  N  46  
MIA  C13    C14     DOUB  N  N  47  
MIA  C13    H131    SING  N  N  48  
MIA  C14    C15     SING  N  N  49  
MIA  C14    C16     SING  N  N  50  
MIA  C15    H151    SING  N  N  51  
MIA  C15    H152    SING  N  N  52  
MIA  C15    H153    SING  N  N  53  
MIA  C16    H161    SING  N  N  54  
MIA  C16    H162    SING  N  N  55  
MIA  C16    H163    SING  N  N  56  
#   #
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
MIA  SMILES            ACDLabs               12.01  "OP(=O)(O)OCC1OC(C(C1O)O)n2cnc3c(NC\C=C(\C)C)nc(nc23)SC"  
MIA  InChI             InChI                 1.03   "InChI=1S/C16H24N5O7PS/c1-8(2)4-5-17-13-10-14(20-16(19-13)30-3)21(7-18-10)15-12(23)11(22)9(28-15)6-27-29(24,25)26/h4,7,9,11-12,15,22-23H,5-6H2,1-3H3,(H,17,19,20)(H2,24,25,26)/t9-,11-,12-,15-/m1/s1"  
MIA  InChIKey          InChI                 1.03   XBXAAXAANNIENQ-SDBHATRESA-N  
MIA  SMILES_CANONICAL  CACTVS                3.385  "CSc1nc(NCC=C(C)C)c2ncn([C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]3O)c2n1"  
MIA  SMILES            CACTVS                3.385  "CSc1nc(NCC=C(C)C)c2ncn([CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O)c2n1"  
MIA  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "CC(=CCNc1c2c(nc(n1)SC)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)C"  
MIA  SMILES            "OpenEye OEToolkits"  2.0.7  "CC(=CCNc1c2c(nc(n1)SC)n(cn2)C3C(C(C(O3)COP(=O)(O)O)O)O)C"  
#   #
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
MIA  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-(3-methylbut-2-en-1-yl)-2-(methylsulfanyl)adenosine 5'-(dihydrogen phosphate)"  
MIA  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.7  "[(2~{R},3~{S},4~{R},5~{R})-5-[6-(3-methylbut-2-enylamino)-2-methylsulfanyl-purin-9-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl dihydrogen 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
MIA  "Create component"    1999-07-08  RCSB  
MIA  "Modify descriptor"   2011-06-04  RCSB  
MIA  "Other modification"  2019-06-13  RCSB  
##
