data_5CI
# 
_chem_comp.id                                    5CI 
_chem_comp.name                                  "8-bromo-5'-{[3-carboxy-2-(carboxymethyl)-2-hydroxypropanoyl]amino}-5'-deoxyadenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H19 Br N6 O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-01-06 
_chem_comp.pdbx_modified_date                    2012-03-09 
_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                        519.261 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5CI 
_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        3V8N 
_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 
5CI O41   O41 O  0 1 N N N 11.077 9.628  16.625 -6.903 -3.039 -0.054 O41 5CI 1  
5CI C51   C51 C  0 1 N N N 11.066 10.321 15.607 -5.939 -2.293 0.509  C51 5CI 2  
5CI O31   O31 O  0 1 N N N 10.793 11.525 15.541 -5.782 -2.313 1.707  O31 5CI 3  
5CI C41   C41 C  0 1 N N N 11.372 9.596  14.320 -5.052 -1.432 -0.353 C41 5CI 4  
5CI C31   C31 C  0 1 N N N 12.857 9.434  14.091 -4.152 -0.574 0.539  C31 5CI 5  
5CI C21   C21 C  0 1 N N N 13.236 7.973  14.257 -5.015 0.383  1.365  C21 5CI 6  
5CI C11   C11 C  0 1 N N N 14.234 7.737  15.394 -5.751 1.319  0.441  C11 5CI 7  
5CI O21   O21 O  0 1 N N N 15.091 8.604  15.605 -5.626 1.209  -0.756 O21 5CI 8  
5CI O11   O11 O  0 1 N N N 14.148 6.661  15.990 -6.545 2.275  0.948  O11 5CI 9  
5CI O71   O71 O  0 1 N N N 13.537 10.202 15.054 -3.406 -1.420 1.416  O71 5CI 10 
5CI C61   C61 C  0 1 N N N 13.101 10.029 12.719 -3.203 0.220  -0.321 C61 5CI 11 
5CI O51   O51 O  0 1 N N N 12.700 11.162 12.530 -3.469 0.426  -1.487 O51 5CI 12 
5CI "N5'" N5* N  0 1 N N N 13.678 9.304  11.768 -2.060 0.702  0.205  N5* 5CI 13 
5CI "C5'" C5* C  0 1 N N N 13.841 9.876  10.416 -1.191 1.565  -0.599 C5* 5CI 14 
5CI "C4'" C4* C  0 1 N N R 15.262 9.753  9.826  0.031  1.970  0.228  C4* 5CI 15 
5CI "O4'" O4* O  0 1 N N N 15.660 8.418  9.634  0.847  0.817  0.492  O4* 5CI 16 
5CI "C3'" C3* C  0 1 N N S 15.299 10.261 8.393  0.892  2.972  -0.565 C3* 5CI 17 
5CI "O3'" O3* O  0 1 N N N 15.313 11.673 8.317  0.999  4.210  0.142  O3* 5CI 18 
5CI "C2'" C2* C  0 1 N N R 16.619 9.683  7.941  2.275  2.284  -0.670 C2* 5CI 19 
5CI "O2'" O2* O  0 1 N N N 17.659 10.591 8.172  3.330  3.228  -0.475 O2* 5CI 20 
5CI "C1'" C1* C  0 1 N N R 16.823 8.496  8.851  2.220  1.264  0.500  C1* 5CI 21 
5CI N9    N9  N  0 1 Y N N 16.913 7.206  8.141  3.131  0.144  0.252  N9  5CI 22 
5CI C8    C8  C  0 1 Y N N 16.018 6.610  7.358  2.932  -0.877 -0.631 C8  5CI 23 
5CI BR8   BR8 BR 0 0 N N N 14.329 7.239  6.811  1.412  -1.074 -1.738 BR8 5CI 24 
5CI N7    N7  N  0 1 Y N N 16.477 5.453  6.956  3.945  -1.695 -0.599 N7  5CI 25 
5CI C5    C5  C  0 1 Y N N 17.669 5.293  7.473  4.854  -1.253 0.303  C5  5CI 26 
5CI C4    C4  C  0 1 Y N N 17.942 6.396  8.225  4.343  -0.068 0.860  C4  5CI 27 
5CI N3    N3  N  0 1 Y N N 19.093 6.476  8.870  5.055  0.573  1.780  N3  5CI 28 
5CI C2    C2  C  0 1 Y N N 19.963 5.514  8.785  6.222  0.106  2.172  C2  5CI 29 
5CI N1    N1  N  0 1 Y N N 19.740 4.447  8.074  6.741  -1.005 1.681  N1  5CI 30 
5CI C6    C6  C  0 1 Y N N 18.614 4.300  7.403  6.104  -1.711 0.752  C6  5CI 31 
5CI N6    N6  N  0 1 N N N 18.412 3.219  6.687  6.658  -2.872 0.241  N6  5CI 32 
5CI H1    H1  H  0 1 N N N 10.840 10.162 17.374 -7.446 -3.575 0.539  H1  5CI 33 
5CI H2    H2  H  0 1 N N N 10.945 10.167 13.482 -4.435 -2.067 -0.988 H2  5CI 34 
5CI H3    H3  H  0 1 N N N 10.909 8.599  14.357 -5.669 -0.785 -0.976 H3  5CI 35 
5CI H4    H4  H  0 1 N N N 12.323 7.396  14.467 -5.734 -0.190 1.950  H4  5CI 36 
5CI H5    H5  H  0 1 N N N 13.685 7.619  13.318 -4.378 0.960  2.035  H5  5CI 37 
5CI H6    H6  H  0 1 N N N 14.841 6.600  16.636 -6.996 2.852  0.317  H6  5CI 38 
5CI H7    H7  H  0 1 N N N 14.252 9.693  15.419 -2.835 -2.054 0.960  H7  5CI 39 
5CI H8    H8  H  0 1 N N N 14.000 8.378  11.966 -1.812 0.477  1.115  H8  5CI 40 
5CI H9    H9  H  0 1 N N N 13.582 10.944 10.463 -0.865 1.026  -1.488 H9  5CI 41 
5CI H10   H10 H  0 1 N N N 13.144 9.359  9.740  -1.740 2.458  -0.896 H10 5CI 42 
5CI H11   H11 H  0 1 N N N 15.977 10.312 10.448 -0.290 2.420  1.168  H11 5CI 43 
5CI H12   H12 H  0 1 N N N 14.471 9.827  7.813  0.471  3.136  -1.557 H12 5CI 44 
5CI H13   H13 H  0 1 N N N 14.475 12.014 8.605  1.530  4.878  -0.312 H13 5CI 45 
5CI H14   H14 H  0 1 N N N 16.565 9.364  6.890  2.384  1.774  -1.627 H14 5CI 46 
5CI H15   H15 H  0 1 N N N 18.481 10.212 7.882  3.349  3.938  -1.132 H15 5CI 47 
5CI H16   H16 H  0 1 N N N 17.716 8.652  9.474  2.458  1.751  1.446  H16 5CI 48 
5CI H17   H17 H  0 1 N N N 20.897 5.603  9.319  6.775  0.651  2.922  H17 5CI 49 
5CI H18   H18 H  0 1 N N N 19.206 2.616  6.761  6.182  -3.379 -0.435 H18 5CI 50 
5CI H19   H19 H  0 1 N N N 17.600 2.743  7.024  7.522  -3.178 0.559  H19 5CI 51 
# 
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 
5CI N6    C6    SING N N 1  
5CI BR8   C8    SING N N 2  
5CI N7    C8    DOUB Y N 3  
5CI N7    C5    SING Y N 4  
5CI C8    N9    SING Y N 5  
5CI C6    C5    DOUB Y N 6  
5CI C6    N1    SING Y N 7  
5CI C5    C4    SING Y N 8  
5CI "C2'" "O2'" SING N N 9  
5CI "C2'" "C3'" SING N N 10 
5CI "C2'" "C1'" SING N N 11 
5CI N1    C2    DOUB Y N 12 
5CI N9    C4    SING Y N 13 
5CI N9    "C1'" SING N N 14 
5CI C4    N3    DOUB Y N 15 
5CI "O3'" "C3'" SING N N 16 
5CI "C3'" "C4'" SING N N 17 
5CI C2    N3    SING Y N 18 
5CI "C1'" "O4'" SING N N 19 
5CI "O4'" "C4'" SING N N 20 
5CI "C4'" "C5'" SING N N 21 
5CI "C5'" "N5'" SING N N 22 
5CI "N5'" C61   SING N N 23 
5CI O51   C61   DOUB N N 24 
5CI C61   C31   SING N N 25 
5CI C31   C21   SING N N 26 
5CI C31   C41   SING N N 27 
5CI C31   O71   SING N N 28 
5CI C21   C11   SING N N 29 
5CI C41   C51   SING N N 30 
5CI C11   O21   DOUB N N 31 
5CI C11   O11   SING N N 32 
5CI O31   C51   DOUB N N 33 
5CI C51   O41   SING N N 34 
5CI O41   H1    SING N N 35 
5CI C41   H2    SING N N 36 
5CI C41   H3    SING N N 37 
5CI C21   H4    SING N N 38 
5CI C21   H5    SING N N 39 
5CI O11   H6    SING N N 40 
5CI O71   H7    SING N N 41 
5CI "N5'" H8    SING N N 42 
5CI "C5'" H9    SING N N 43 
5CI "C5'" H10   SING N N 44 
5CI "C4'" H11   SING N N 45 
5CI "C3'" H12   SING N N 46 
5CI "O3'" H13   SING N N 47 
5CI "C2'" H14   SING N N 48 
5CI "O2'" H15   SING N N 49 
5CI "C1'" H16   SING N N 50 
5CI C2    H17   SING N N 51 
5CI N6    H18   SING N N 52 
5CI N6    H19   SING N N 53 
# 
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 
5CI SMILES           ACDLabs              12.01 "O=C(O)CC(O)(C(=O)NCC3OC(n2c(Br)nc1c(ncnc12)N)C(O)C3O)CC(=O)O" 
5CI InChI            InChI                1.03  
"InChI=1S/C16H19BrN6O9/c17-15-22-8-11(18)20-4-21-12(8)23(15)13-10(29)9(28)5(32-13)3-19-14(30)16(31,1-6(24)25)2-7(26)27/h4-5,9-10,13,28-29,31H,1-3H2,(H,19,30)(H,24,25)(H,26,27)(H2,18,20,21)/t5-,9-,10-,13-/m1/s1" 
5CI InChIKey         InChI                1.03  QQTQAKWRRPPHOE-MSTPSEHLSA-N 
5CI SMILES_CANONICAL CACTVS               3.370 "Nc1ncnc2n([C@@H]3O[C@H](CNC(=O)C(O)(CC(O)=O)CC(O)=O)[C@@H](O)[C@H]3O)c(Br)nc12" 
5CI SMILES           CACTVS               3.370 "Nc1ncnc2n([CH]3O[CH](CNC(=O)C(O)(CC(O)=O)CC(O)=O)[CH](O)[CH]3O)c(Br)nc12" 
5CI SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(c(n2)Br)[C@H]3[C@@H]([C@@H]([C@H](O3)CNC(=O)C(CC(=O)O)(CC(=O)O)O)O)O)N" 
5CI SMILES           "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(c(n2)Br)C3C(C(C(O3)CNC(=O)C(CC(=O)O)(CC(=O)O)O)O)O)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 
5CI "SYSTEMATIC NAME" ACDLabs              12.01 "8-bromo-5'-{[3-carboxy-2-(carboxymethyl)-2-hydroxypropanoyl]amino}-5'-deoxyadenosine"                                            
5CI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "3-[[(2R,3S,4R,5R)-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methylcarbamoyl]-3-oxidanyl-pentanedioic 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 
5CI "Create component" 2012-01-06 RCSB 
# 
