data_YVN
# 
_chem_comp.id                                    YVN 
_chem_comp.name                                  N-({(1R,2R,3S)-2-(methylcarbamoyl)-3-[4-(phosphonooxy)phenyl]cyclopropyl}carbonyl)-L-valyl-L-aspartamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H30 N5 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-08-01 
_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                        527.465 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     YVN 
_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        2HUW 
_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 
YVN OBH  OBH  O 0 1 N N N 22.387 81.731 22.758 7.426  1.758  -1.189 OBH  YVN 1  
YVN PBF  PBF  P 0 1 N N N 22.449 82.515 24.159 7.242  2.106  0.237  PBF  YVN 2  
YVN OBI  OBI  O 0 1 N N N 22.401 84.075 23.784 8.668  2.470  0.889  OBI  YVN 3  
YVN OBG  OBG  O 0 1 N N N 23.656 82.154 24.943 6.258  3.374  0.357  OBG  YVN 4  
YVN OBE  OBE  O 0 1 N N N 21.060 82.159 24.908 6.599  0.852  1.017  OBE  YVN 5  
YVN CBD  CBD  C 0 1 Y N N 20.691 83.087 25.847 5.440  0.398  0.473  CBD  YVN 6  
YVN CBC  CBC  C 0 1 Y N N 21.374 83.189 27.082 4.225  0.923  0.888  CBC  YVN 7  
YVN CBB  CBB  C 0 1 Y N N 20.870 84.029 28.101 3.047  0.459  0.334  CBB  YVN 8  
YVN CBJ  CBJ  C 0 1 Y N N 19.520 83.834 25.637 5.470  -0.587 -0.503 CBJ  YVN 9  
YVN CBK  CBK  C 0 1 Y N N 19.018 84.674 26.650 4.290  -1.047 -1.055 CBK  YVN 10 
YVN CBA  CBA  C 0 1 Y N N 19.684 84.772 27.888 3.079  -0.527 -0.635 CBA  YVN 11 
YVN CAZ  CAZ  C 0 1 N N S 19.062 85.611 29.038 1.794  -1.031 -1.237 CAZ  YVN 12 
YVN CAF  CAF  C 0 1 N N R 19.777 86.917 29.471 1.249  -2.366 -0.726 CAF  YVN 13 
YVN CAC  CAC  C 0 1 N N N 21.080 87.312 28.760 2.039  -3.076 0.343  CAC  YVN 14 
YVN OAD  OAD  O 0 1 N N N 21.113 87.503 27.546 2.976  -2.520 0.875  OAD  YVN 15 
YVN NAB  NAB  N 0 1 N N N 22.128 87.466 29.569 1.705  -4.330 0.707  NAB  YVN 16 
YVN CAA  CAA  C 0 1 N N N 22.752 88.631 29.634 2.473  -5.020 1.746  CAA  YVN 17 
YVN CAG  CAG  C 0 1 N N R 18.514 86.994 28.628 0.555  -1.058 -0.340 CAG  YVN 18 
YVN CAH  CAH  C 0 1 N N N 17.274 87.492 29.375 -0.776 -0.761 -0.981 CAH  YVN 19 
YVN OAI  OAI  O 0 1 N N N 17.120 87.270 30.576 -0.836 -0.512 -2.166 OAI  YVN 20 
YVN NAJ  NAJ  N 0 1 N N N 16.404 88.162 28.615 -1.900 -0.771 -0.237 NAJ  YVN 21 
YVN CAK  CAK  C 0 1 N N S 15.147 88.761 29.125 -3.194 -0.482 -0.860 CAK  YVN 22 
YVN CAW  CAW  C 0 1 N N N 14.324 89.308 27.937 -3.762 -1.764 -1.472 CAW  YVN 23 
YVN CAX  CAX  C 0 1 N N N 13.027 89.978 28.413 -2.873 -2.213 -2.633 CAX  YVN 24 
YVN CAY  CAY  C 0 1 N N N 15.151 90.311 27.127 -3.805 -2.862 -0.408 CAY  YVN 25 
YVN CAL  CAL  C 0 1 N N N 14.308 87.758 29.952 -4.147 0.043  0.182  CAL  YVN 26 
YVN OAM  OAM  O 0 1 N N N 13.775 88.116 31.000 -3.846 -0.000 1.356  OAM  YVN 27 
YVN NAN  NAN  N 0 1 N N N 14.208 86.521 29.457 -5.334 0.561  -0.190 NAN  YVN 28 
YVN CAO  CAO  C 0 1 N N S 13.419 85.485 30.155 -6.218 1.161  0.812  CAO  YVN 29 
YVN CAT  CAT  C 0 1 N N N 14.336 84.491 30.889 -7.053 0.084  1.455  CAT  YVN 30 
YVN OAV  OAV  O 0 1 N N N 13.903 83.409 31.288 -6.923 -1.071 1.110  OAV  YVN 31 
YVN NAU  NAU  N 0 1 N N N 15.593 84.890 31.048 -7.945 0.405  2.413  NAU  YVN 32 
YVN CAP  CAP  C 0 1 N N N 12.503 84.751 29.154 -7.136 2.182  0.136  CAP  YVN 33 
YVN CAQ  CAQ  C 0 1 N N N 13.286 84.026 28.044 -6.309 3.323  -0.401 CAQ  YVN 34 
YVN OAS  OAS  O 0 1 N N N 14.447 84.334 27.774 -5.105 3.319  -0.257 OAS  YVN 35 
YVN NAR  NAR  N 0 1 N N N 12.613 83.059 27.428 -6.908 4.346  -1.041 NAR  YVN 36 
YVN HOBI HOBI H 0 0 N N N 22.392 84.592 24.581 9.114  3.217  0.468  HOBI YVN 37 
YVN HOBG HOBG H 0 0 N N N 24.402 82.077 24.360 6.091  3.658  1.267  HOBG YVN 38 
YVN HBC  HBC  H 0 1 N N N 22.280 82.625 27.246 4.199  1.693  1.645  HBC  YVN 39 
YVN HBB  HBB  H 0 1 N N N 21.391 84.104 29.044 2.101  0.868  0.657  HBB  YVN 40 
YVN HBJ  HBJ  H 0 1 N N N 19.001 83.764 24.692 6.415  -0.994 -0.832 HBJ  YVN 41 
YVN HBK  HBK  H 0 1 N N N 18.118 85.246 26.477 4.312  -1.814 -1.815 HBK  YVN 42 
YVN HAZ  HAZ  H 0 1 N N N 18.688 84.726 29.574 1.646  -0.798 -2.292 HAZ  YVN 43 
YVN HAF  HAF  H 0 1 N N N 20.109 87.317 30.441 0.743  -3.011 -1.443 HAF  YVN 44 
YVN HNAB HNAB H 0 0 N N N 22.443 86.699 30.128 0.955  -4.775 0.282  HNAB YVN 45 
YVN HAA1 HAA1 H 0 0 N N N 22.925 88.897 30.687 2.420  -4.453 2.675  HAA1 YVN 46 
YVN HAA2 HAA2 H 0 0 N N N 23.717 88.560 29.111 2.058  -6.016 1.904  HAA2 YVN 47 
YVN HAA3 HAA3 H 0 0 N N N 22.133 89.405 29.158 3.513  -5.106 1.432  HAA3 YVN 48 
YVN HAG  HAG  H 0 1 N N N 18.238 87.451 27.666 0.670  -0.711 0.687  HAG  YVN 49 
YVN HNAJ HNAJ H 0 0 N N N 16.613 88.266 27.643 -1.852 -0.970 0.712  HNAJ YVN 50 
YVN HAK  HAK  H 0 1 N N N 15.414 89.583 29.806 -3.061 0.266  -1.641 HAK  YVN 51 
YVN HAW  HAW  H 0 1 N N N 14.060 88.452 27.299 -4.771 -1.574 -1.839 HAW  YVN 52 
YVN HAX1 HAX1 H 0 0 N N N 13.074 90.138 29.500 -1.891 -2.494 -2.252 HAX1 YVN 53 
YVN HAX2 HAX2 H 0 0 N N N 12.907 90.946 27.905 -3.329 -3.070 -3.129 HAX2 YVN 54 
YVN HAX3 HAX3 H 0 0 N N N 12.171 89.330 28.175 -2.766 -1.395 -3.346 HAX3 YVN 55 
YVN HAY1 HAY1 H 0 0 N N N 15.349 91.203 27.740 -4.438 -2.542 0.420  HAY1 YVN 56 
YVN HAY2 HAY2 H 0 0 N N N 16.105 89.848 26.834 -4.210 -3.775 -0.844 HAY2 YVN 57 
YVN HAY3 HAY3 H 0 0 N N N 14.593 90.603 26.225 -2.796 -3.051 -0.041 HAY3 YVN 58 
YVN HNAN HNAN H 0 0 N N N 14.674 86.293 28.602 -5.603 0.536  -1.122 HNAN YVN 59 
YVN HAO  HAO  H 0 1 N N N 12.790 85.978 30.911 -5.619 1.660  1.573  HAO  YVN 60 
YVN HAU1 HAU1 H 0 0 N N N 16.078 84.162 31.533 -8.050 1.329  2.688  HAU1 YVN 61 
YVN HAU2 HAU2 H 0 0 N N N 15.983 85.758 30.739 -8.483 -0.288 2.827  HAU2 YVN 62 
YVN HAP1 HAP1 H 0 0 N N N 11.915 84.004 29.707 -7.670 1.704  -0.685 HAP1 YVN 63 
YVN HAP2 HAP2 H 0 0 N N N 11.867 85.507 28.671 -7.852 2.564  0.863  HAP2 YVN 64 
YVN HAR1 HAR1 H 0 0 N N N 13.221 82.669 26.737 -7.871 4.350  -1.156 HAR1 YVN 65 
YVN HAR2 HAR2 H 0 0 N N N 11.674 82.775 27.620 -6.376 5.080  -1.386 HAR2 YVN 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 
YVN OBH PBF  DOUB N N 1  
YVN PBF OBI  SING N N 2  
YVN PBF OBE  SING N N 3  
YVN PBF OBG  SING N N 4  
YVN OBI HOBI SING N N 5  
YVN OBG HOBG SING N N 6  
YVN OBE CBD  SING N N 7  
YVN CBD CBJ  DOUB Y N 8  
YVN CBD CBC  SING Y N 9  
YVN CBC CBB  DOUB Y N 10 
YVN CBC HBC  SING N N 11 
YVN CBB CBA  SING Y N 12 
YVN CBB HBB  SING N N 13 
YVN CBJ CBK  SING Y N 14 
YVN CBJ HBJ  SING N N 15 
YVN CBK CBA  DOUB Y N 16 
YVN CBK HBK  SING N N 17 
YVN CBA CAZ  SING N N 18 
YVN CAZ CAG  SING N N 19 
YVN CAZ CAF  SING N N 20 
YVN CAZ HAZ  SING N N 21 
YVN CAF CAG  SING N N 22 
YVN CAF CAC  SING N N 23 
YVN CAF HAF  SING N N 24 
YVN CAC OAD  DOUB N N 25 
YVN CAC NAB  SING N N 26 
YVN NAB CAA  SING N N 27 
YVN NAB HNAB SING N N 28 
YVN CAA HAA1 SING N N 29 
YVN CAA HAA2 SING N N 30 
YVN CAA HAA3 SING N N 31 
YVN CAG CAH  SING N N 32 
YVN CAG HAG  SING N N 33 
YVN CAH NAJ  SING N N 34 
YVN CAH OAI  DOUB N N 35 
YVN NAJ CAK  SING N N 36 
YVN NAJ HNAJ SING N N 37 
YVN CAK CAW  SING N N 38 
YVN CAK CAL  SING N N 39 
YVN CAK HAK  SING N N 40 
YVN CAW CAY  SING N N 41 
YVN CAW CAX  SING N N 42 
YVN CAW HAW  SING N N 43 
YVN CAX HAX1 SING N N 44 
YVN CAX HAX2 SING N N 45 
YVN CAX HAX3 SING N N 46 
YVN CAY HAY1 SING N N 47 
YVN CAY HAY2 SING N N 48 
YVN CAY HAY3 SING N N 49 
YVN CAL NAN  SING N N 50 
YVN CAL OAM  DOUB N N 51 
YVN NAN CAO  SING N N 52 
YVN NAN HNAN SING N N 53 
YVN CAO CAP  SING N N 54 
YVN CAO CAT  SING N N 55 
YVN CAO HAO  SING N N 56 
YVN CAT NAU  SING N N 57 
YVN CAT OAV  DOUB N N 58 
YVN NAU HAU1 SING N N 59 
YVN NAU HAU2 SING N N 60 
YVN CAP CAQ  SING N N 61 
YVN CAP HAP1 SING N N 62 
YVN CAP HAP2 SING N N 63 
YVN CAQ NAR  SING N N 64 
YVN CAQ OAS  DOUB N N 65 
YVN NAR HAR1 SING N N 66 
YVN NAR HAR2 SING N N 67 
# 
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 
YVN SMILES           ACDLabs              10.04 O=C(N)CC(C(=O)N)NC(=O)C(NC(=O)C2C(C(=O)NC)C2c1ccc(OP(=O)(O)O)cc1)C(C)C 
YVN InChI            InChI                1.02b 
;InChI=1/C21H30N5O9P/c1-9(2)17(21(31)25-12(18(23)28)8-13(22)27)26-20(30)16-14(15(16)19(29)24-3)10-4-6-11(7-5-10)35-36(32,33)34/h4-7,9,12,14-17H,8H2,1-3H3,(H2,22,27)(H2,23,28)(H,24,29)(H,25,31)(H,26,30)(H2,32,33,34)/t12-,14-,15+,16+,17-/m0/s1/f/h24-26,32-33H,22-23H2
;
YVN InChIKey         InChI                1.02b LVYNAUCEOQBVSW-BFGMZVHBDP 
YVN SMILES_CANONICAL CACTVS               3.341 CNC(=O)[C@H]1[C@@H]([C@H]1c2ccc(O[P](O)(O)=O)cc2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(N)=O 
YVN SMILES           CACTVS               3.341 CNC(=O)[CH]1[CH]([CH]1c2ccc(O[P](O)(O)=O)cc2)C(=O)N[CH](C(C)C)C(=O)N[CH](CC(N)=O)C(N)=O 
YVN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)N)NC(=O)[C@@H]1[C@H]([C@H]1C(=O)NC)c2ccc(cc2)OP(=O)(O)O 
YVN SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)C(C(=O)NC(CC(=O)N)C(=O)N)NC(=O)C1C(C1C(=O)NC)c2ccc(cc2)OP(=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 
YVN "SYSTEMATIC NAME" ACDLabs              10.04 N-({(1R,2R,3S)-2-(methylcarbamoyl)-3-[4-(phosphonooxy)phenyl]cyclopropyl}carbonyl)-L-valyl-L-aspartamide                                                                    
YVN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[4-[(1S,2R,3R)-2-[[(2S)-1-[[(2S)-1,4-diamino-1,4-dioxo-butan-2-yl]amino]-3-methyl-1-oxo-butan-2-yl]carbamoyl]-3-(methylcarbamoyl)cyclopropyl]phenyl] dihydrogen phosphate" 
# 
