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 H26 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                    2009-01-07 
_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                        463.446 
_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        ? 
_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 -2.429 1.833  -6.970 OP3    MIA 1  
MIA P      P    P 0 1 N N N 27.665 43.645 -30.146 -1.619 0.509  -6.543 P      MIA 2  
MIA OP1    O1P  O 0 1 N N N 28.001 42.610 -29.130 -2.577 -0.561 -6.186 OP1    MIA 3  
MIA OP2    O2P  O 0 1 N N N 26.242 44.014 -30.375 -0.703 0.020  -7.774 OP2    MIA 4  
MIA "O5'"  O5*  O 0 1 N N N 28.469 44.977 -29.789 -0.684 0.837  -5.275 "O5'"  MIA 5  
MIA "C5'"  C5*  C 0 1 N N N 29.783 44.912 -29.203 0.004  -0.370 -4.946 "C5'"  MIA 6  
MIA "C4'"  C4*  C 0 1 N N R 30.486 46.249 -29.309 0.915  -0.126 -3.741 "C4'"  MIA 7  
MIA "O4'"  O4*  O 0 1 N N N 30.537 46.647 -30.706 0.135  0.265  -2.591 "O4'"  MIA 8  
MIA "C3'"  C3*  C 0 1 N N S 29.834 47.435 -28.613 1.613  -1.437 -3.317 "C3'"  MIA 9  
MIA "O3'"  O3*  O 0 1 N N N 30.117 47.523 -27.221 2.937  -1.496 -3.853 "O3'"  MIA 10 
MIA "C2'"  C2*  C 0 1 N N R 30.402 48.619 -29.385 1.656  -1.358 -1.773 "C2'"  MIA 11 
MIA "O2'"  O2*  O 0 1 N N N 31.697 49.014 -28.973 3.007  -1.368 -1.308 "O2'"  MIA 12 
MIA "C1'"  C1*  C 0 1 N N R 30.438 48.059 -30.804 0.975  -0.010 -1.449 "C1'"  MIA 13 
MIA N9     N9   N 0 1 Y N N 29.165 48.396 -31.428 0.163  -0.127 -0.235 N9     MIA 14 
MIA C8     C8   C 0 1 Y N N 28.145 47.581 -31.863 -1.143 -0.511 -0.172 C8     MIA 15 
MIA N7     N7   N 0 1 Y N N 27.092 48.236 -32.275 -1.549 -0.504 1.063  N7     MIA 16 
MIA C5     C5   C 0 1 Y N N 27.433 49.556 -32.119 -0.531 -0.116 1.870  C5     MIA 17 
MIA C6     C6   C 0 1 Y N N 26.736 50.727 -32.385 -0.387 0.070  3.256  C6     MIA 18 
MIA N6     N6   N 0 1 N N N 25.457 50.809 -32.838 -1.449 -0.157 4.114  N6     MIA 19 
MIA N1     N1   N 0 1 Y N N 27.387 51.915 -32.138 0.788  0.471  3.724  N1     MIA 20 
MIA C2     C2   C 0 1 Y N N 28.658 51.886 -31.641 1.812  0.692  2.909  C2     MIA 21 
MIA N3     N3   N 0 1 Y N N 29.405 50.813 -31.372 1.718  0.533  1.598  N3     MIA 22 
MIA C4     C4   C 0 1 Y N N 28.723 49.682 -31.625 0.579  0.130  1.046  C4     MIA 23 
MIA S10    S10  S 0 1 N N N 29.436 53.434 -31.351 3.346  1.223  3.594  S10    MIA 24 
MIA C11    C11  C 0 1 N N N 31.066 52.985 -30.692 2.906  1.274  5.349  C11    MIA 25 
MIA C12    C12  C 0 1 N N N 24.884 52.233 -32.581 -1.282 0.042  5.555  C12    MIA 26 
MIA C13    C13  C 0 1 N N N 23.650 52.745 -33.358 -2.597 -0.276 6.270  C13    MIA 27 
MIA C14    C14  C 0 1 N N N 23.528 54.128 -33.291 -2.423 -0.067 7.775  C14    MIA 28 
MIA C15    C15  C 0 1 N N N 22.852 55.030 -34.243 -3.737 -0.386 8.490  C15    MIA 29 
MIA C16    C16  C 0 1 N N N 24.529 54.909 -32.423 -1.322 -0.994 8.295  C16    MIA 30 
MIA HOP3   3HOP H 0 0 N N N 28.058 43.829 -32.210 -2.976 1.593  -7.731 HOP3   MIA 31 
MIA HOP2   2HOP H 0 0 N N N 25.883 44.294 -29.541 -0.095 0.745  -7.974 HOP2   MIA 32 
MIA "H5'"  1H5* H 0 1 N N N 29.747 44.546 -28.150 0.605  -0.689 -5.797 "H5'"  MIA 33 
MIA "H5''" 2H5* H 0 0 N N N 30.391 44.089 -29.645 -0.720 -1.147 -4.701 "H5''" MIA 34 
MIA "H4'"  H4*  H 0 1 N N N 31.465 46.054 -28.813 1.656  0.639  -3.976 "H4'"  MIA 35 
MIA "H3'"  H3*  H 0 1 N N N 28.721 47.368 -28.628 1.033  -2.301 -3.641 "H3'"  MIA 36 
MIA "HO3'" H3T  H 0 0 N Y N 29.710 48.263 -26.786 3.321  -2.332 -3.556 "HO3'" MIA 37 
MIA "H2'"  H2*  H 0 1 N N N 29.796 49.544 -29.243 1.095  -2.183 -1.333 "H2'"  MIA 38 
MIA "HO2'" 2HO* H 0 0 N N N 32.051 49.752 -29.454 3.394  -2.208 -1.593 "HO2'" MIA 39 
MIA "H1'"  H1*  H 0 1 N N N 31.291 48.468 -31.392 1.723  0.773  -1.331 "H1'"  MIA 40 
MIA H8     H8   H 0 1 N N N 28.169 46.478 -31.880 -1.752 -0.782 -1.022 H8     MIA 41 
MIA HN6    HN6  H 0 1 N N N 24.864 50.082 -32.437 -2.304 -0.450 3.760  HN6    MIA 42 
MIA H111   1H11 H 0 0 N N N 31.559 53.967 -30.507 3.770  1.593  5.932  H111   MIA 43 
MIA H112   2H11 H 0 0 N N N 31.032 52.313 -29.802 2.087  1.978  5.498  H112   MIA 44 
MIA H113   3H11 H 0 0 N N N 31.649 52.292 -31.342 2.595  0.281  5.675  H113   MIA 45 
MIA H121   1H12 H 0 0 N N N 24.671 52.329 -31.490 -0.498 -0.618 5.925  H121   MIA 46 
MIA H122   2H12 H 0 0 N N N 25.710 52.969 -32.718 -1.005 1.078  5.749  H122   MIA 47 
MIA H131   1H13 H 0 0 N N N 23.662 52.391 -34.415 -3.381 0.383  5.900  H131   MIA 48 
MIA H132   2H13 H 0 0 N N N 22.717 52.239 -33.014 -2.873 -1.313 6.076  H132   MIA 49 
MIA H14    H14  H 0 1 N N N 22.588 53.711 -32.858 -2.146 0.968  7.969  H14    MIA 50 
MIA H151   1H15 H 0 0 N N N 22.754 56.139 -34.189 -3.613 -0.237 9.563  H151   MIA 51 
MIA H152   2H15 H 0 0 N N N 23.308 54.815 -35.237 -4.521 0.273  8.120  H152   MIA 52 
MIA H153   3H15 H 0 0 N N N 21.812 54.640 -34.341 -4.014 -1.423 8.297  H153   MIA 53 
MIA H161   1H16 H 0 0 N N N 24.431 56.018 -32.369 -1.598 -2.031 8.102  H161   MIA 54 
MIA H162   2H16 H 0 0 N N N 24.514 54.492 -31.388 -0.385 -0.767 7.786  H162   MIA 55 
MIA H163   3H16 H 0 0 N N N 25.565 54.651 -32.743 -1.198 -0.845 9.368  H163   MIA 56 
# 
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    SING N N 47 
MIA C13   H131   SING N N 48 
MIA C13   H132   SING N N 49 
MIA C14   C15    SING N N 50 
MIA C14   C16    SING N N 51 
MIA C14   H14    SING N N 52 
MIA C15   H151   SING N N 53 
MIA C15   H152   SING N N 54 
MIA C15   H153   SING N N 55 
MIA C16   H161   SING N N 56 
MIA C16   H162   SING N N 57 
MIA C16   H163   SING N N 58 
# 
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              10.04 "O=P(O)(O)OCC3OC(n2cnc1c(nc(SC)nc12)NCCC(C)C)C(O)C3O" 
MIA InChI            InChI                1.02b 
"InChI=1/C16H26N5O7PS/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/h7-9,11-12,15,22-23H,4-6H2,1-3H3,(H,17,19,20)(H2,24,25,26)/t9-,11-,12-,15-/m1/s1/f/h17,24-25H" 
MIA InChIKey         InChI                1.02b LCHGAOHLDYRACA-AWVQMGAODT 
MIA SMILES_CANONICAL CACTVS               3.341 "CSc1nc(NCCC(C)C)c2ncn([C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]3O)c2n1" 
MIA SMILES           CACTVS               3.341 "CSc1nc(NCCC(C)C)c2ncn([CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O)c2n1" 
MIA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(C)CCNc1c2c(nc(n1)SC)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O" 
MIA SMILES           "OpenEye OEToolkits" 1.5.0 "CC(C)CCNc1c2c(nc(n1)SC)n(cn2)C3C(C(C(O3)COP(=O)(O)O)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 
MIA "SYSTEMATIC NAME" ACDLabs              10.04 
;N-(3-methylbutyl)-2-(methylsulfanyl)adenosine 5'-(dihydrogen phosphate)
;
MIA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(3-methylbutylamino)-2-methylsulfanyl-purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate" 
# 
