data_MAD
# 
_chem_comp.id                                    MAD 
_chem_comp.name                                  "6-HYDRO-1-METHYLADENOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H16 N5 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               A 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-08-28 
_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                        361.248 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     MAD 
_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        1H3E 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
MAD P      P    P 0 1 N N N 142.800 27.386 10.352 -1.005 0.125  -5.019 P      MAD 1  
MAD OP1    O1P  O 0 1 N N N 142.757 28.646 11.140 -2.129 1.111  -5.615 OP1    MAD 2  
MAD OP2    O2P  O 0 1 N N N 144.108 26.786 10.003 -1.593 -1.213 -4.793 OP2    MAD 3  
MAD "O5'"  O5*  O 0 1 N N N 141.945 26.262 11.096 -0.459 0.715  -3.623 "O5'"  MAD 4  
MAD "C5'"  C5*  C 0 1 N N N 140.694 26.576 11.748 0.529  -0.199 -3.147 "C5'"  MAD 5  
MAD "C4'"  C4*  C 0 1 N N R 140.855 26.500 13.252 1.091  0.304  -1.817 "C4'"  MAD 6  
MAD "O4'"  O4*  O 0 1 N N N 141.354 25.178 13.580 0.044  0.378  -0.825 "O4'"  MAD 7  
MAD "C3'"  C3*  C 0 1 N N S 141.905 27.480 13.783 2.108  -0.707 -1.242 "C3'"  MAD 8  
MAD "O3'"  O3*  O 0 1 N N N 141.627 27.818 15.141 3.444  -0.302 -1.548 "O3'"  MAD 9  
MAD "C2'"  C2*  C 0 1 N N R 143.197 26.676 13.702 1.863  -0.660 0.284  "C2'"  MAD 10 
MAD "O2'"  O2*  O 0 1 N N N 144.172 27.108 14.635 3.042  -0.228 0.967  "O2'"  MAD 11 
MAD "C1'"  C1*  C 0 1 N N R 142.697 25.265 14.013 0.725  0.371  0.448  "C1'"  MAD 12 
MAD N9     N9   N 0 1 Y N N 143.449 24.181 13.384 -0.189 -0.044 1.513  N9     MAD 13 
MAD C8     C8   C 0 1 Y N N 144.562 24.230 12.575 -1.285 -0.849 1.370  C8     MAD 14 
MAD N7     N7   N 0 1 Y N N 144.998 23.049 12.206 -1.874 -1.003 2.528  N7     MAD 15 
MAD C5     C5   C 0 1 Y N N 144.108 22.164 12.805 -1.201 -0.319 3.454  C5     MAD 16 
MAD C6     C6   C 0 1 N N N 144.020 20.763 12.807 -1.388 -0.118 4.900  C6     MAD 17 
MAD N6     N6   N 0 1 N N N 144.872 19.965 12.159 -2.520 -0.345 5.524  N6     MAD 18 
MAD N1     N1   N 0 1 N N N 143.006 20.204 13.510 -0.234 0.343  5.538  N1     MAD 19 
MAD CM1    CM1  C 0 1 N N N 142.816 18.726 13.587 0.018  0.017  6.944  CM1    MAD 20 
MAD C2     C2   C 0 1 N N N 142.150 20.995 14.157 0.654  1.096  4.830  C2     MAD 21 
MAD N3     N3   N 0 1 N N N 142.130 22.320 14.230 0.752  1.059  3.525  N3     MAD 22 
MAD C4     C4   C 0 1 Y N N 143.149 22.850 13.525 -0.105 0.298  2.822  C4     MAD 23 
MAD OXT    OXT  O 0 1 N Y N 142.025 27.617 8.968  0.213  0.007  -6.064 OXT    MAD 24 
MAD H1P    H1P  H 0 1 N N N 141.917 29.030 11.363 -2.428 0.723  -6.448 H1P    MAD 25 
MAD "H5'"  1H5* H 0 1 N N N 139.861 25.930 11.385 1.336  -0.274 -3.877 "H5'"  MAD 26 
MAD "H5''" 2H5* H 0 0 N N N 140.290 27.563 11.422 0.078  -1.180 -3.003 "H5''" MAD 27 
MAD "H4'"  H4*  H 0 1 N N N 139.875 26.677 13.753 1.560  1.279  -1.948 "H4'"  MAD 28 
MAD "H3'"  H3*  H 0 1 N N N 141.960 28.393 13.146 1.914  -1.706 -1.631 "H3'"  MAD 29 
MAD HA     HA   H 0 1 N N N 142.278 28.426 15.470 4.032  -0.968 -1.167 HA     MAD 30 
MAD "H2'"  H2*  H 0 1 N N N 143.611 26.717 12.667 1.547  -1.637 0.650  "H2'"  MAD 31 
MAD HB     HB   H 0 1 N N N 144.977 26.607 14.585 3.730  -0.880 0.776  HB     MAD 32 
MAD "H1'"  H1*  H 0 1 N N N 142.722 25.117 15.118 1.136  1.357  0.665  "H1'"  MAD 33 
MAD H8     H8   H 0 1 N N N 145.042 25.174 12.266 -1.614 -1.290 0.441  H8     MAD 34 
MAD H6     H6   H 0 1 N N N 144.669 19.096 12.654 -2.585 -0.194 6.480  H6     MAD 35 
MAD HM11   1HM1 H 0 0 N N N 141.981 18.266 14.166 0.964  0.461  7.255  HM11   MAD 36 
MAD HM12   2HM1 H 0 0 N N N 143.770 18.280 13.954 -0.788 0.414  7.560  HM12   MAD 37 
MAD HM13   3HM1 H 0 0 N N N 142.761 18.336 12.544 0.068  -1.064 7.063  HM13   MAD 38 
MAD H2     H2   H 0 1 N N N 141.347 20.477 14.708 1.311  1.759  5.374  H2     MAD 39 
MAD HXT    HXT  H 0 1 N N N 142.052 26.811 8.464  0.567  0.899  -6.183 HXT    MAD 40 
# 
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 
MAD P     OP1    SING N N 1  
MAD P     OP2    DOUB N N 2  
MAD P     "O5'"  SING N N 3  
MAD P     OXT    SING N N 4  
MAD OP1   H1P    SING N N 5  
MAD "O5'" "C5'"  SING N N 6  
MAD "C5'" "C4'"  SING N N 7  
MAD "C5'" "H5'"  SING N N 8  
MAD "C5'" "H5''" SING N N 9  
MAD "C4'" "O4'"  SING N N 10 
MAD "C4'" "C3'"  SING N N 11 
MAD "C4'" "H4'"  SING N N 12 
MAD "O4'" "C1'"  SING N N 13 
MAD "C3'" "O3'"  SING N N 14 
MAD "C3'" "C2'"  SING N N 15 
MAD "C3'" "H3'"  SING N N 16 
MAD "O3'" HA     SING N N 17 
MAD "C2'" "O2'"  SING N N 18 
MAD "C2'" "C1'"  SING N N 19 
MAD "C2'" "H2'"  SING N N 20 
MAD "O2'" HB     SING N N 21 
MAD "C1'" N9     SING N N 22 
MAD "C1'" "H1'"  SING N N 23 
MAD N9    C8     SING Y N 24 
MAD N9    C4     SING Y N 25 
MAD C8    N7     DOUB Y N 26 
MAD C8    H8     SING N N 27 
MAD N7    C5     SING Y N 28 
MAD C5    C6     SING N N 29 
MAD C5    C4     DOUB Y N 30 
MAD C6    N6     DOUB N N 31 
MAD C6    N1     SING N N 32 
MAD N6    H6     SING N N 33 
MAD N1    CM1    SING N N 34 
MAD N1    C2     SING N N 35 
MAD CM1   HM11   SING N N 36 
MAD CM1   HM12   SING N N 37 
MAD CM1   HM13   SING N N 38 
MAD C2    N3     DOUB N N 39 
MAD C2    H2     SING N N 40 
MAD N3    C4     SING N N 41 
MAD OXT   HXT    SING N N 42 
# 
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 
MAD SMILES           ACDLabs              10.04 "O=P(O)(O)OCC3OC(n2cnc1c2N=CN(C1=[N@H])C)C(O)C3O"                                                                                                                               
MAD InChI            InChI                1.02b "InChI=1/C11H16N5O7P/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(18)7(17)5(23-11)2-22-24(19,20)21/h3-5,7-8,11-12,17-18H,2H2,1H3,(H2,19,20,21)/b12-9-/t5-,7-,8-,11-/m1/s1/f/h19-20H" 
MAD InChIKey         InChI                1.02b BKBYKEWNXKDACS-HCIVTNLXDR                                                                                                                                                       
MAD SMILES_CANONICAL CACTVS               3.341 "CN1C=Nc2n(cnc2C1=N)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]3O"                                                                                                               
MAD SMILES           CACTVS               3.341 "CN1C=Nc2n(cnc2C1=N)[CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O"                                                                                                                     
MAD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CN1C=Nc2c(ncn2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)C1=N"                                                                                                               
MAD SMILES           "OpenEye OEToolkits" 1.5.0 "CN1C=Nc2c(ncn2C3C(C(C(O3)COP(=O)(O)O)O)O)C1=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 
MAD "SYSTEMATIC NAME" ACDLabs              10.04 
;1-methyladenosine 5'-(dihydrogen phosphate)
;
MAD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-imino-1-methyl-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
