Prodrugs of Aza Nucleosides Based on Proton Transfer Reaction

Prodrugs of Aza nucleosides Based on Proton Transfer Reaction

Rafik Karaman*

Faculty of Pharmacy,

Al-QudsUniversity, P. O. Box 20002, Jerusalem, Palestine

Fax: + (972) 22790413

E-mail:

Supplementary Material

Xyz Cartesian Coordinates for 1GM-7GM and 1TS-7TS.

1GM

O 2.239130 2.982892 1.032071 -0.649762

H 2.234763 2.065037 1.369990 0.348993

O 2.136960 0.330447 1.971249 -0.522701

C 1.711017 -0.557630 0.943157 0.359918

O 0.539585 0.074354 0.424222 -0.616393

C -0.709456 -0.659994 0.373379 0.233724

C -0.595995 -1.849183 -0.613422 -0.185164

C -1.170564 -1.177462 1.756764 -0.186300

C -1.806390 0.261181 -0.155037 0.056967

C -1.752694 1.621109 -0.476715 0.146690

C -2.854618 2.291795 -1.012013 -0.087762

C -4.045802 1.604653 -1.211072 -0.096545

C -4.141553 0.259548 -0.851710 -0.119398

C -3.040568 -0.412489 -0.325007 0.102357

C -3.035214 -1.864659 0.128172 -0.049322

C -1.950081 -2.594605 -0.710438 -0.179828

C -2.559201 -1.860462 1.611233 -0.183910

C -4.386745 -2.569108 -0.000042 -0.331243

C 3.334131 0.297354 -0.818580 -0.133058

C 2.750996 -0.780390 -0.136433 0.109932

C 3.144695 -2.084784 -0.452373 -0.130297

C 4.281934 0.063690 -1.812852 -0.089016

C 4.661112 -1.243122 -2.132955 -0.076562

C 4.094256 -2.317762 -1.449033 -0.085728

C 3.195776 -0.182515 2.789717 -0.098249

C -0.770962 3.494339 0.830604 -0.207803

C 0.142780 2.952914 -1.426554 -0.206696

N -0.527981 2.415653 -0.193053 -0.512684

H 0.345585 2.116061 -2.094292 0.167608

H 1.073284 3.422507 -1.109791 0.185832

H -0.515208 3.671695 -1.913787 0.159390

H 0.140251 1.735878 0.217669 0.375206

H -1.280735 3.044986 1.682420 0.161347

H -1.398474 4.269301 0.391971 0.156024

H 0.201369 3.884888 1.127442 0.198231

H 3.112047 3.335079 1.244147 0.324642

H 3.389099 0.574044 3.550718 0.141234

H 4.104497 -0.364305 2.206744 0.136994

H 3.060222 1.315251 -0.558748 0.082434

H 4.731783 0.901602 -2.336811 0.107283

H 4.392409 -3.334375 -1.684884 0.113766

H 5.400923 -1.420294 -2.907231 0.115400

H -0.439965 -1.893889 2.143324 0.112476

H 0.190151 -2.524817 -0.265426 0.108629

H -1.202600 -0.340733 2.460257 0.117565

H -0.274614 -1.462728 -1.584224 0.123254

H -2.277213 -2.663269 -1.751895 0.121208

H -3.303809 -1.346528 2.226072 0.119917

H -1.854807 -3.620472 -0.339641 0.115402

H -2.514525 -2.894990 1.966214 0.118075

H -4.305159 -3.602152 0.350750 0.120400

H -5.158788 -2.077223 0.600167 0.118008

H -4.728864 -2.602166 -1.039240 0.118256

H -5.082561 -0.261663 -0.983886 0.118798

H -4.903012 2.121619 -1.628885 0.126853

H -2.790889 3.345308 -1.262958 0.111080

H 2.712276 -2.926398 0.083729 0.093551

H 2.886194 -1.113515 3.279933 0.124729

H 1.445699 -1.519357 1.398461 0.096369

1TS

O 0.529671 0.004649 0.268778 -0.574746

H 0.405821 1.206068 0.341936 0.403376

N -0.459709 2.337643 -0.242869 -0.598426

C -1.725322 1.649277 -0.501204 0.223261

C -1.857459 0.291477 -0.198938 0.037443

C -3.117327 -0.336110 -0.326293 0.109284

C -4.201570 0.386522 -0.818812 -0.129419

C -4.046602 1.727534 -1.175985 -0.092654

C -2.819586 2.359422 -1.007831 -0.089899

C 0.232631 2.781714 -1.481269 -0.191943

C -0.608373 3.456507 0.729058 -0.191836

C 1.717135 -0.580506 0.915707 0.334847

O 2.036973 0.370361 1.902684 -0.518897

H 2.418284 2.197357 1.286785 0.331599

O 2.582201 3.089288 0.939239 -0.623630

C 2.989012 -0.096797 2.874821 -0.103906

C 2.794327 -0.839161 -0.105058 0.116292

C 3.487356 0.213641 -0.721023 -0.131200

C 4.469199 -0.066412 -1.669119 -0.088931

C 4.771355 -1.389423 -2.003718 -0.072777

C 4.092809 -2.438542 -1.383648 -0.085681

C 3.107483 -2.162828 -0.435348 -0.126787

C -0.802004 -0.674206 0.308245 0.186842

C -1.210165 -1.139939 1.718603 -0.185690

C -0.731058 -1.877699 -0.652204 -0.180242

C -2.117874 -2.571004 -0.699076 -0.179351

H -2.470330 -2.645467 -1.731343 0.127351

C -3.151622 -1.781348 0.150229 -0.050509

C -4.530769 -2.437795 0.074472 -0.331004

C -2.633522 -1.767548 1.620670 -0.185773

H -2.617639 -2.794156 1.999798 0.120046

H -2.049353 -3.592033 -0.310000 0.116557

H 0.039957 -2.573790 -0.307914 0.107876

H -0.502222 -1.885051 2.093924 0.111493

H -0.424771 -1.517633 -1.637293 0.133746

H -1.192130 -0.291372 2.407905 0.127558

H -3.335054 -1.206591 2.244003 0.126902

H -4.478885 -3.468596 0.437672 0.118795

H -4.904659 -2.469600 -0.953579 0.120980

H -5.264473 -1.906806 0.688853 0.120538

H -5.170994 -0.087359 -0.922674 0.114245

H -4.890505 2.285912 -1.567716 0.122865

H -2.714853 3.410238 -1.256313 0.111622

H -1.187792 4.279649 0.298284 0.132465

H 0.388763 3.807583 0.998294 0.174783

H -1.125238 3.088732 1.617197 0.133853

H 1.194926 3.210759 -1.197079 0.169147

H -0.360670 3.529956 -2.017579 0.138028

H 0.390051 1.919268 -2.131401 0.137837

H 3.432199 3.361782 1.306842 0.323393

H 3.104870 0.711119 3.596924 0.151580

H 3.952132 -0.324522 2.408163 0.145373

H 2.606521 -0.987618 3.386065 0.132701

H 3.274495 1.244419 -0.453746 0.099047

H 5.004532 0.749071 -2.145159 0.117468

H 5.539356 -1.600561 -2.741084 0.121898

H 4.332243 -3.467495 -1.631689 0.119187

H 2.587319 -2.983483 0.052836 0.096969

H 1.396964 -1.518325 1.379893 0.116331

2GM

C -3.343895 0.825885 -0.424334

C -2.019357 1.331922 -0.351903

C -0.927543 0.455024 -0.001963

C -1.268725 -0.914474 0.246566

C -2.567232 -1.365632 0.187485

C -3.619345 -0.490733 -0.155315

C -1.775728 2.705593 -0.614173

C -0.512087 3.233466 -0.512824

C 0.565790 2.399743 -0.150855

C 0.367084 1.055369 0.071968

O 1.477016 0.286538 0.467951

C 2.412338 -0.049179 -0.548945

O 1.954869 -1.255392 -1.119819

C 2.839915 -1.791991 -2.112571

N -0.207942 -1.891467 0.635943

C -0.389854 -3.276136 0.079928

C 0.004566 -1.921464 2.127238

H -2.617295 3.335734 -0.883302

H -0.334798 4.287920 -0.693890

H 1.559988 2.812698 -0.006696

H -2.803004 -2.402194 0.396998

H -4.633865 -0.869750 -0.204125

H -4.142840 1.510193 -0.691812

H 0.670226 -1.556756 0.206576

H 0.249808 -0.915101 2.459709

H 0.828742 -2.600597 2.350402

H -0.914079 -2.266288 2.601342

H -1.200266 -3.787381 0.596209

H 0.541522 -3.819564 0.240827

H -0.602922 -3.198702 -0.984935

H 3.380389 -0.185339 -0.051336

H 2.474840 0.746855 -1.302073

H 2.957879 -1.090480 -2.946220

H 2.383937 -2.711424 -2.479206

H 3.823137 -2.016818 -1.682228

H 2.837923 1.648840 1.293664

O 3.477143 2.290346 1.627058

H 3.128473 2.562133 2.485165

2TS

N -0.339026 -1.581174 -0.565044

H -1.195522 -0.406081 -0.057924

O -1.116788 0.736930 -0.447059

C -2.148289 1.565699 0.327997

O -3.273700 0.815792 0.459871

H -2.680306 -0.610107 1.666552

O -2.377427 -1.341515 2.220901

H -3.167838 -1.658804 2.673130

H -1.708054 1.755532 1.307329

C -4.173620 0.791815 -0.673925

H -5.050763 0.234839 -0.349028

H -3.707850 0.294605 -1.529003

H -4.461557 1.812817 -0.940824

C 0.230417 1.208163 -0.249865

C 0.490729 2.555942 -0.252317

H -0.286578 3.285667 -0.443172

C 1.810611 2.999487 0.002019

H 2.013509 4.064634 0.008285

C 2.814209 2.094411 0.249509

H 3.821568 2.437196 0.462616

C 2.562045 0.697307 0.213542

C 1.236654 0.226632 -0.067470

C 1.002430 -1.171957 -0.172167

C 2.027543 -2.065992 0.045517

C 3.323172 -1.602760 0.372976

C 3.588024 -0.256186 0.443235

H 4.588800 0.097742 0.669157

H 4.112480 -2.325449 0.549744

H 1.854255 -3.132868 -0.028106

H -0.231456 -0.610874 -2.457686

H 0.155671 -2.345944 -2.490346

C -0.495190 -1.584886 -2.047286

H -1.533830 -1.814129 -2.295359

C -0.771870 -2.886316 0.003596

H -1.834433 -3.013779 -0.206510

H -0.224615 -3.719528 -0.448749

H -0.636881 -2.869505 1.083004

H -2.291285 2.474436 -0.259678

3GM

C 1.194391 -0.940171 0.412453

C 0.333091 -0.135870 -0.601983

C 0.994899 1.110203 -1.246286

C 2.489839 1.261247 -0.918693

C 3.205121 -0.084957 -1.042692

C 2.562595 -1.260285 -0.274343

O 2.123006 -2.271026 -1.215447

C 0.726180 -2.333273 -1.036427

O 0.133456 -1.149294 -1.591839

O 0.533326 -2.207357 0.344953

O -0.882603 0.187715 0.065355

C -2.024853 0.539042 -0.778610

O -2.056627 1.914897 -1.034613

C -2.451741 2.786774 0.035966

N 2.675858 1.980771 0.446977

C 2.565006 3.469108 0.267560

O 3.547492 -1.735274 0.585856

C 3.305938 -2.967191 1.290765

C 3.942643 1.642298 1.178046

C -3.280314 -0.039381 -0.152645

C -3.234769 -1.018978 0.844067

C -4.419345 -1.564764 1.343289

C -5.652654 -1.143333 0.847615

C -5.701354 -0.176438 -0.159380

C -4.521891 0.370300 -0.660316

O 0.332269 1.791724 1.924887

H -0.134038 1.221066 1.272882

H -6.571580 -1.570609 1.236704

H -6.657418 0.149104 -0.557305

H -4.559566 1.117158 -1.447878

H -1.845959 0.080942 -1.754306

H -2.276559 -1.365681 1.212457

H -4.375546 -2.324858 2.117406

H -1.713478 2.790185 0.844844

H -2.506649 3.783522 -0.404065

H -3.430583 2.515560 0.438310

H 0.031235 1.513101 2.799301

H 0.422675 2.000880 -0.981551

H 1.881100 1.744694 1.085808

H 1.653020 3.700668 -0.280322

H 2.521722 3.936471 1.251034

H 3.436435 3.825872 -0.283115

H 2.948616 1.952351 -1.630649

H 3.972863 0.573993 1.390080

H 4.799986 1.927094 0.566621

H 3.166174 -0.339231 -2.105384

H 4.261110 -0.027459 -0.777942

H 3.036509 -3.761937 0.593304

H 4.250487 -3.207236 1.778723

H 2.520105 -2.857711 2.044316

H 1.238976 -0.567172 1.432184

H 0.299056 -3.231131 -1.471941

H 0.906995 1.007695 -2.330924

H 3.954078 2.210199 2.109028

3TS

O -0.805318 0.144251 -0.001939

H -0.511729 0.769212 0.707520

O -0.075479 1.629707 1.608428

H 0.913302 1.771951 1.285458

N 2.264482 2.103465 0.592650

C 3.408054 1.932695 1.516976

C 2.020438 3.553998 0.391518

C 2.452015 1.446619 -0.757335

C 3.357386 0.198504 -0.808188

C 2.752868 -1.091671 -0.219568

O 3.707568 -1.608373 0.638863

C 3.526038 -2.917606 1.204828

C 1.338469 -0.912035 0.383221

O 0.794317 -2.232967 0.274143

O 2.395909 -2.047129 -1.278714

C 1.034043 -2.316110 -1.098230

C 0.485901 -0.179698 -0.704111

C 1.085543 1.076527 -1.365440

O 0.266236 -1.197193 -1.630444

C -2.622811 2.726248 -0.201342

O -2.126540 1.775302 -1.174370

C -2.064625 0.447603 -0.861513

C -3.245255 -0.170450 -0.146964

C -3.117766 -1.088095 0.900948

C -4.258067 -1.665459 1.462927

C -5.524481 -1.343396 0.976765

C -5.653116 -0.445419 -0.085257

C -4.520274 0.137217 -0.647663

H -4.621796 0.828012 -1.479385

H -6.634591 -0.200562 -0.478278

H -6.407600 -1.796725 1.415466

H -4.152247 -2.374167 2.278161

H -2.136621 -1.369881 1.263852

H -1.818580 -0.084297 -1.781565

H -3.572162 2.401800 0.226135

H -1.885139 2.878708 0.590065

H -2.766809 3.649975 -0.760807

H 0.720807 -3.244824 -1.564240

H -0.116337 1.494477 2.563432

H 1.283459 -0.533581 1.397841

H 3.329720 -3.655373 0.424382

H 2.717830 -2.936210 1.941905

H 4.472192 -3.146814 1.695055

H 3.565721 0.878481 1.750098

H 3.184777 2.463357 2.445817

H 4.337950 2.346378 1.105333

H 4.320862 0.368078 -0.328228

H 1.778825 4.018318 1.350219

H 2.902103 4.053555 -0.030257

H 2.924300 2.187828 -1.415220

H 1.175391 3.707465 -0.282323

H 1.222955 0.842927 -2.423605

H 0.375776 1.904063 -1.318110

H 3.566570 0.007978 -1.864423

4GM

C -2.153064 -1.716463 0.646233

O -3.057351 -1.534117 -0.424428

H -3.756893 0.136150 -0.216116

O -4.085571 1.040816 -0.084408

C -3.955337 -2.637337 -0.609638

H -4.555349 -2.400011 -1.481959

H -4.605956 -2.776474 0.256488

H -1.659236 -2.685171 0.572053

H -2.666070 -1.633308 1.606617

H -5.042465 1.001518 -0.037410

C -1.635392 2.644609 1.307495

H -1.267995 3.665816 1.284133

H -1.249589 2.129339 2.181068

H -2.719811 2.617715 1.290791

O -1.238262 -0.649983 0.543302

N -1.153941 1.938380 0.067893

H -1.558254 0.993164 0.113002

C -1.681978 2.599670 -1.179379

H -2.763908 2.533178 -1.144799

H -1.346790 3.630978 -1.208702

H -1.295492 2.061708 -2.039406

C 0.315781 1.735919 0.022151

C 0.863409 0.454196 0.069697

C 2.259028 0.313169 -0.093313

C 3.062623 1.437736 -0.236087

C 2.498908 2.712142 -0.229932

C 1.125684 2.862879 -0.112564

H 0.691631 3.851800 -0.134439

H 3.127406 3.584644 -0.332208

H 4.129840 1.330610 -0.354439

C 4.252156 -1.278685 -0.344082

H 4.557999 -0.844201 -1.296758

H 4.522355 -2.334859 -0.362480

H 4.831189 -0.805507 0.450099

C 2.748422 -1.128567 -0.109949

C 1.945679 -1.854137 -1.230286

H 2.253543 -2.900168 -1.256717

H 2.205965 -1.421758 -2.196338

C 2.337198 -1.767071 1.245093

H 2.584918 -2.829231 1.218252

H 2.924392 -1.325661 2.050132

C 0.824362 -1.564458 1.502252

H 0.333936 -2.522558 1.682663

C 0.165996 -0.890111 0.280050

C 0.412971 -1.747638 -0.979931

H -0.013679 -2.740971 -0.837670

H -0.101082 -1.295442 -1.827643

H 0.645273 -0.941588 2.378293

H -3.397494 -3.557222 -0.794343

4TS

N -1.302286 1.770467 0.068997

H -1.636841 0.291953 0.340419

O -1.213111 -0.841072 0.311994

C -2.099187 -1.968011 0.657469

O -3.273817 -1.849135 -0.040498

H -3.995518 -0.100665 0.282626

O -4.383216 0.763843 0.486954

H -5.218889 0.570586 0.927824

C -3.226707 -2.261984 -1.422090

H -4.253743 -2.231432 -1.781629

H -2.840904 -3.283525 -1.494765

H -2.605878 -1.582595 -2.012443

H -1.545659 -2.880979 0.425243

C 0.265244 -0.906269 0.224142

C 0.820204 0.491130 -0.004910

C 0.143282 1.714249 -0.086781

C 0.860595 2.893239 -0.316983

C 2.243774 2.859219 -0.452107

C 2.929060 1.647656 -0.347588

C 2.229869 0.463300 -0.123973

C 2.856884 -0.916850 0.029461

C 2.404172 -1.456246 1.418798

C 2.222199 -1.828769 -1.060440

C 0.671598 -1.796268 -0.974022

C 0.853933 -1.475949 1.525284

H 2.590157 -2.850329 -0.923806

H 2.807175 -2.463592 1.559848

H 0.274179 -2.807424 -0.839078

H 0.490997 -2.498436 1.675652

H 0.227967 -1.387148 -1.885461

H 2.552588 -1.499619 -2.048832

C 4.382830 -0.933746 -0.078616

H 4.848341 -0.319719 0.698196

H 4.723231 -0.569727 -1.052507

H 4.755884 -1.955124 0.041266

H 4.008281 1.632600 -0.442482

H 2.790940 3.779384 -0.626872

H 0.334488 3.839348 -0.385626

C -2.011826 2.207244 -1.162926

H -3.083566 2.087246 -0.997511

H -1.786877 3.253110 -1.395441

H -1.691310 1.584776 -2.000421

C -1.735808 2.562310 1.252270

H -2.807262 2.405157 1.381366

H -1.525997 3.627596 1.113137

H -1.199290 2.208976 2.134397

H 2.830237 -0.828233 2.205332

H 0.503745 -0.874575 2.368606

H -2.330016 -1.895475 1.720434

5GM

O -1.547114 -1.154696 0.640918

H -1.578542 0.396911 1.444539

O -1.560704 1.287079 1.863582

H -0.370090 1.960434 0.747109

N 0.059196 2.450025 -0.073135

C 1.307526 3.125600 0.416337

C -0.968669 3.478137 -0.454827

C 0.262596 1.440178 -1.238968

C -0.815624 0.344479 -1.186298

C 1.658863 0.823409 -1.323905

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O 2.205093 -1.527175 -0.939433

C 1.195086 -2.371398 -0.437226

O 1.086961 -2.042993 0.917619

C 0.789460 -0.668610 0.654726

C -0.468060 -0.836489 -0.242096

O -0.066433 -1.974489 -1.004910

C -2.712958 -1.790354 0.052826

O -3.594781 -0.890458 -0.524342

C -4.492227 -0.250694 0.390169

H -5.204723 0.310375 -0.215585

H -3.965023 0.437317 1.061791

H -5.036864 -0.993991 0.984992

H -2.370667 -2.474776 -0.723660

H -1.793633 0.747529 -0.920779

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H -1.862957 2.976169 -0.820717

H -1.221710 4.064024 0.428571

H -0.554503 4.123439 -1.230743

H 1.028095 3.795399 1.230452

H 1.747356 3.704504 -0.396878

H 2.018693 2.379876 0.770469

H 2.451234 1.571949 -1.311910

H 1.705869 0.340059 -2.303572

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H 3.163789 -0.919570 2.193890

H 4.688666 -0.201511 1.605070

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H 1.403548 -3.418407 -0.633817

H -3.163285 -2.336148 0.888416

H -1.532511 1.141537 2.818033

5TS

N -0.165776 2.371221 0.019819

H -1.008990 1.652957 1.049815

O -1.714523 1.056170 1.635068

H -1.590416 -0.152789 1.146073

O -1.457534 -1.053396 0.744480

C -0.352562 -0.803747 -0.254873

C -0.754108 0.300379 -1.251802

C 0.191969 1.513266 -1.181006

C 0.976782 3.080016 0.644563

C -1.184404 3.371964 -0.393327

C 3.936526 -0.644910 1.131734

C 0.901100 -0.561904 0.644897

O 3.210328 0.286691 0.309713

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H 3.401659 -0.876511 2.057274

H 4.874035 -0.141944 1.368005

H 4.141496 -1.566444 0.583507

O 1.264053 -1.917581 0.928017

C -2.670667 -1.860361 0.331969

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H -5.189131 -0.081071 -0.691372

H -2.227677 -2.725359 -0.156760

H -0.696499 -0.140898 -2.249591

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H -5.070838 -0.977372 0.840850

H -4.072596 0.491084 0.588314

H -1.622621 1.234978 2.579753

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H 0.602746 3.647406 1.500348

H -1.531488 3.921458 0.484596

H 1.451067 3.785364 -0.049209

H -0.771906 4.085516 -1.117346

H -2.043336 2.869885 -0.843306

H 0.019698 2.126415 -2.073596

H 2.361258 1.839100 -1.140561

C 1.649649 1.024977 -1.272670

C 2.039120 -0.112917 -0.306879

C -4.511866 -0.387356 0.106128

H -3.115469 -2.102340 1.301516

6GM

N -1.005393 1.586319 0.288472

C -1.456148 0.193379 0.058125

C -2.794604 -0.176235 -0.010441

C -3.094147 -1.524678 -0.205125

C -2.066927 -2.469029 -0.304511

C -0.727739 -2.087907 -0.214659

C -0.417794 -0.739448 -0.037979

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C 1.657079 -0.381848 -1.150748

O 2.962466 -0.071790 -0.885154

C 3.256928 1.313658 -0.659652

H 2.868583 1.929811 -1.480274

H 4.342817 1.396236 -0.628922

H 2.848050 1.650703 0.298547

H 0.068643 -2.823393 -0.250978

H 1.621429 -1.423788 -1.475679

H 1.192886 0.273230 -1.909670

H -3.591147 0.554654 0.089957

H -4.130036 -1.839083 -0.265566

H -2.312649 -3.517265 -0.437444

H -2.472104 2.617687 -0.853498

H -1.017978 2.131291 -1.762727

H -0.941266 3.507545 -0.616502

C -1.386123 2.532532 -0.819120

C -1.395530 2.111035 1.648075

H -1.041801 1.406984 2.400453

H -0.934827 3.089238 1.791704

H -2.480797 2.195904 1.693536

H 0.023381 1.471313 0.289871

H 3.135009 -0.995051 0.972127

O 3.214736 -1.377974 1.856082

H 4.085710 -1.793560 1.858315

6TS

N -1.610473 -1.349207 -0.109394

H -0.190846 -1.299809 -0.704222

O 0.604511 -0.438475 -0.404869

C 1.486484 -1.097542 0.701751

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H 3.345217 1.126829 0.097039

O 3.620569 2.025505 -0.123915

H 4.328626 2.230539 0.498889

C 3.421409 -1.567101 -0.595795

H 3.165819 -2.628728 -0.516106

H 4.491478 -1.433037 -0.448678

H 3.122280 -1.166367 -1.566456

H 1.230256 -2.156908 0.606105

H 1.163772 -0.647210 1.640013

C -0.327300 0.592828 -0.248363

C -0.010789 1.930122 -0.083280

C -1.088558 2.812784 0.054626

C -2.403802 2.336280 0.113854

C -2.686057 0.964304 0.054777

H -3.704443 0.615673 0.183089

H -3.225100 3.036681 0.219770

H -0.897765 3.876751 0.143988

H 1.018616 2.274121 -0.135743

H -2.741711 -2.178795 1.494518

C -1.690631 -2.023118 1.221466

H -1.192473 -2.994249 1.166954

H -1.220693 -1.403521 1.985132

C -2.577667 -1.954382 -1.069893

H -2.384211 -3.027472 -1.131659

H -2.435876 -1.505607 -2.054105

H -3.612314 -1.801912 -0.748937

C -1.622626 0.072021 -0.060045

7GM

O -3.262859 -0.343724 -0.160827

H -2.312039 1.039239 -0.655493

O -1.740048 1.797812 -0.903756

H -1.966831 2.033051 -1.810749

C -4.667821 -0.609452 -0.116341

C -2.511158 -1.104986 0.774518

O -1.171356 -0.725664 0.684406

C -0.482759 -1.185032 -0.492685

C 1.002844 -0.992905 -0.294415

C 1.847635 -2.106264 -0.378634

C 3.225391 -1.997775 -0.203226

C 3.790092 -0.757362 0.081185

C 2.973630 0.368246 0.174820

C 1.599917 0.250218 -0.026676

N 0.765551 1.476546 0.095192

C 1.306739 2.658702 -0.661803

C 0.496933 1.830467 1.536209

H -5.077734 -0.394232 0.877154

H -5.137589 0.044839 -0.849348

H -4.874893 -1.653302 -0.377272

H -2.833454 -0.885274 1.798781

H -2.638973 -2.178272 0.562160

H 3.850794 -2.880017 -0.277763

H 4.858712 -0.658741 0.232882

H 3.420410 1.328772 0.402742

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H 2.197191 3.045917 -0.171277

H 1.438299 2.097805 2.014547

H -0.197877 2.669925 1.554763

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H -0.693658 -2.246994 -0.657308

H -0.844936 -0.634113 -1.368497

H 1.409811 -3.077491 -0.583540

7TS

N -0.451768 1.388569 -0.276698

H 0.833710 0.571539 -0.503870

O 1.041195 -0.532297 -0.953977

C 2.459383 -0.720722 -1.110497

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C 4.503701 -0.468226 0.072191

C 0.270332 -1.440426 -0.066978

C -1.146411 -0.959778 -0.008237

C -2.144175 -1.943205 0.102057

C -3.483678 -1.596425 0.202390

C -3.837455 -0.244970 0.211687

C -2.848481 0.724507 0.100324

C -1.494694 0.370060 -0.042629

C -0.537710 1.970914 -1.650866

C -0.329027 2.419555 0.784546

H -0.497863 1.151708 -2.373782

H 0.316222 2.635309 -1.807233

H -1.457305 2.542528 -1.797664

H -0.206811 1.926371 1.747833

H 0.559238 3.020272 0.583509

H -1.205671 3.074348 0.797204

H -3.125971 1.772859 0.109400

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H -4.242903 -2.366570 0.277982

H -1.857375 -2.990194 0.109095

H 0.367149 -2.437888 -0.496122

H 0.733554 -1.396677 0.923317

H 2.649603 -1.795411 -1.226292

H 2.718657 -0.183907 -2.029238

H 4.678459 -1.547848 0.131032

H 5.021000 -0.053765 -0.798993

H 4.873348 0.015033 0.974810