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//
// Copyright (C) 2020-2021 Brian P Kelley, Joann Prescott-Roy and other RDKit
// contributors
//
// @@ All Rights Reserved @@
// This file is part of the RDKit.
// The contents are covered by the terms of the BSD license
// which is included in the file license.txt, found at the root
// of the RDKit source tree.
//
#include "catch.hpp"
#include <GraphMol/RDKitBase.h>
#include <GraphMol/ROMol.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/SmilesParse/SmilesWrite.h>
#include <GraphMol/Deprotect/Deprotect.h>
#include <boost/algorithm/string.hpp>
using namespace RDKit;
using namespace RDKit::Deprotect;
TEST_CASE("Deprotection basics", "[deprotect]") {
const auto dps = getDeprotections();
DeprotectData cp = dps[0];
CHECK(cp == dps[0]);
CHECK(dps[0] == cp);
CHECK(dps[1] != dps[0]);
}
TEST_CASE("Standard deprotections", "[deprotect]") {
SECTION("simple deprotections") {
auto m = "N(C(=O)OC(C)(C)C)Cc1ccccc1NC(=O)OC(C)(C)C"_smiles;
auto res = deprotect(*m);
REQUIRE(res);
CHECK(MolToSmiles(*res) == "NCc1ccccc1N");
CHECK(res->getProp<int>("DEPROTECTION_COUNT") == 2);
std::vector<std::string> expected{"Boc", "Boc"};
CHECK(res->getProp<std::vector<std::string>>("DEPROTECTIONS") == expected);
}
SECTION("test deprotection examples") {
for (auto &data : getDeprotections()) {
std::vector<DeprotectData> vect = {data};
std::vector<std::string> examples;
boost::split(examples, data.example, boost::is_any_of(">"));
std::unique_ptr<ROMol> start(SmilesToMol(examples[0]));
std::unique_ptr<ROMol> end(SmilesToMol(examples[2]));
// check the one
auto res = deprotect(*start, vect);
CHECK(MolToSmiles(*res) == MolToSmiles(*end));
// check them all
res = deprotect(*start);
CHECK(MolToSmiles(*res) == MolToSmiles(*end));
}
}
}
TEST_CASE("Standard deprotections in place", "[deprotect]") {
SECTION("simple deprotections") {
auto m = "N(C(=O)OC(C)(C)C)Cc1ccccc1NC(=O)OC(C)(C)C"_smiles;
CHECK(deprotectInPlace(*m));
CHECK(MolToSmiles(*m) == "NCc1ccccc1N");
CHECK(m->getProp<int>("DEPROTECTION_COUNT") == 2);
std::vector<std::string> expected{"Boc", "Boc"};
CHECK(m->getProp<std::vector<std::string>>("DEPROTECTIONS") == expected);
}
SECTION("test deprotection examples") {
for (auto &data : getDeprotections()) {
std::vector<DeprotectData> vect = {data};
std::vector<std::string> examples;
boost::split(examples, data.example, boost::is_any_of(">"));
std::unique_ptr<RWMol> end(SmilesToMol(examples[2]));
// check the one
{
std::unique_ptr<RWMol> start(SmilesToMol(examples[0]));
deprotectInPlace(*start, vect);
CHECK(MolToSmiles(*start) == MolToSmiles(*end));
}
// check them all
{
std::unique_ptr<RWMol> start(SmilesToMol(examples[0]));
deprotectInPlace(*start);
CHECK(MolToSmiles(*start) == MolToSmiles(*end));
}
}
}
}
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