Implement Compound CRUD (#22)

Co-authored-by: Tim Lorsbach <tim@lorsba.ch>
Reviewed-on: enviPath/enviPy#22

epdb/models.py

@@ -281,58 +281,121 @@ class Compound(EnviPathModel, AliasMixin, ScenarioMixin):
     def structures(self):
         return CompoundStructure.objects.filter(compound=self)
 
+    @property
+    def normalized_structure(self):
+        return CompoundStructure.objects.get(compound=self, normalized_structure=True)
+
     @property
     def url(self):
         return '{}/compound/{}'.format(self.package.url, self.uuid)
 
-    # @property
-    # def related_pathways(self):
-    #     pathways = Node.objects.filter(node_labels__in=[self.default_structure]).values_list('pathway', flat=True)
-    #     return Pathway.objects.filter(package=self.package, id__in=set(pathways)).order_by('name')
+    @transaction.atomic
+    def set_default_structure(self, cs: 'CompoundStructure'):
+        if cs.compound != self:
+            raise ValueError("Attempt to set a CompoundStructure stored in a different compound as default")
 
-    # @property
-    # def related_reactions(self):
-    #     return (
-    #             Reaction.objects.filter(package=self.package, educts__in=[self.default_structure])
-    #             |
-    #             Reaction.objects.filter(package=self.package, products__in=[self.default_structure])
-    #     ).order_by('name')
+        self.default_structure = cs
+        self.save()
+
+    @property
+    def related_pathways(self):
+        pathways = Node.objects.filter(node_labels__in=[self.default_structure]).values_list('pathway', flat=True)
+        return Pathway.objects.filter(package=self.package, id__in=set(pathways)).order_by('name')
+
+    @property
+    def related_reactions(self):
+        return (
+                Reaction.objects.filter(package=self.package, educts__in=[self.default_structure])
+                |
+                Reaction.objects.filter(package=self.package, products__in=[self.default_structure])
+        ).order_by('name')
 
     @staticmethod
     @transaction.atomic
-    def create(package: Package, smiles: str, name: str = None, description: str = None, *args, **kwargs):
+    def create(package: Package, smiles: str, name: str = None, description: str = None, *args, **kwargs) -> 'Compound':
 
-        # Pre check
-        # Validity of SMILES etc
+        if smiles is None or smiles == '':
+            raise ValueError('SMILES is required')
 
+        smiles = smiles.strip()
+
+        parsed = FormatConverter.from_smiles(smiles)
+        if parsed is None:
+            raise ValueError('Given SMILES is invalid')
+
+        standardized_smiles = FormatConverter.standardize(smiles)
+
+        # Check if we find a direct match for a given SMILES
         if CompoundStructure.objects.filter(smiles=smiles, compound__package=package).exists():
             return CompoundStructure.objects.get(smiles=smiles, compound__package=package).compound
 
+        # Check if we can find the standardized one
+        if CompoundStructure.objects.filter(smiles=standardized_smiles, compound__package=package).exists():
+            # TODO should we add a structure?
+            return CompoundStructure.objects.get(smiles=standardized_smiles, compound__package=package).compound
+
         # Generate Compound
         c = Compound()
         c.package = package
-        if name is not None:
+
+        # For name and description we have defaults so only set them if they carry a real value
+        if name is not None and name != '':
             c.name = name
 
-        if description is not None:
+        if description is not None and description != '':
             c.description = description
 
         c.save()
 
-        normalized_smiles = smiles  # chem.normalize(smiles)
+        is_standardized = standardized_smiles == smiles
 
-        if normalized_smiles != smiles:
-            _ = CompoundStructure.create(c, normalized_smiles, name='Normalized structure of {}'.format(name),
+        if not is_standardized:
+            _ = CompoundStructure.create(c, standardized_smiles, name='Normalized structure of {}'.format(name),
                                          description='{} (in its normalized form)'.format(description),
                                          normalized_structure=True)
 
-        cs = CompoundStructure.create(c, smiles, name=name, description=description)
+        cs = CompoundStructure.create(c, smiles, name=name, description=description, normalized_structure=is_standardized)
 
         c.default_structure = cs
         c.save()
 
         return c
 
+    @transaction.atomic
+    def add_structure(self, smiles: str, name: str = None, description: str = None, default_structure: bool = False,
+                      *args, **kwargs) -> 'CompoundStructure':
+
+        if smiles is None or smiles == '':
+            raise ValueError('SMILES is required')
+
+        smiles = smiles.strip()
+
+        parsed = FormatConverter.from_smiles(smiles)
+        if parsed is None:
+            raise ValueError('Given SMILES is invalid')
+
+        standardized_smiles = FormatConverter.standardize(smiles)
+
+        is_standardized = standardized_smiles == smiles
+
+        if self.normalized_structure.smiles != standardized_smiles:
+            raise ValueError('The standardized SMILES does not match the compounds standardized one!')
+
+        if is_standardized:
+            CompoundStructure.objects.get(smiles__in=smiles, compound__package=self.package)
+
+        # Check if we find a direct match for a given SMILES and/or its standardized SMILES
+        if CompoundStructure.objects.filter(smiles__in=smiles, compound__package=self.package).exists():
+            return CompoundStructure.objects.get(smiles__in=smiles, compound__package=self.package)
+
+        cs = CompoundStructure.create(self, smiles, name=name, description=description, normalized_structure=is_standardized)
+
+        if default_structure:
+            self.default_structure = cs
+            self.save()
+
+        return cs
+
     class Meta:
         unique_together = [('uuid', 'package')]
 
@@ -391,6 +454,10 @@ class CompoundStructure(EnviPathModel, AliasMixin, ScenarioMixin):
     def InChIKey(self):
         return FormatConverter.InChIKey(self.smiles)
 
+    @property
+    def canonical_smiles(self):
+        return FormatConverter.canonicalize(self.smiles)
+
     @property
     def as_svg(self):
         return IndigoUtils.mol_to_svg(self.smiles)
@@ -401,10 +468,10 @@ class Rule(PolymorphicModel, EnviPathModel, AliasMixin, ScenarioMixin):
 
     # I think this only affects Django Admin which we are barely using
     # # https://github.com/django-polymorphic/django-polymorphic/issues/229
-    # _non_polymorphic = models.Manager()
-    #
-    # class Meta:
-    #     base_manager_name = '_non_polymorphic'
+    _non_polymorphic = models.Manager()
+
+    class Meta:
+        base_manager_name = '_non_polymorphic'
 
     @abc.abstractmethod
     def apply(self, *args, **kwargs):

epdb/views.py

@@ -684,7 +684,7 @@ def package_compound(request, package_uuid, compound_uuid):
 
         return render(request, 'objects/compound.html', context)
 
-    if request.method == 'POST':
+    elif request.method == 'POST':
         if hidden := request.POST.get('hidden', None):
             if hidden == 'delete-compound':
                 current_compound.delete()
@@ -706,6 +706,8 @@ def package_compound(request, package_uuid, compound_uuid):
             return redirect(current_compound.url)
         else:
             return HttpResponseBadRequest()
+    else:
+        return HttpResponseBadRequest()
 
 
 # https://envipath.org/package/<uuid>/compound/<uuid>/structure
@@ -724,7 +726,7 @@ def package_compound_structures(request, package_uuid, compound_uuid):
         reviewed_compound_structure_qs = CompoundStructure.objects.none()
         unreviewed_compound_structure_qs = CompoundStructure.objects.none()
 
-        if package.reviewed:
+        if current_package.reviewed:
             reviewed_compound_structure_qs = current_compound.structures.order_by('name')
         else:
             unreviewed_compound_structure_qs = current_compound.structures.order_by('name')
@@ -734,13 +736,24 @@ def package_compound_structures(request, package_uuid, compound_uuid):
 
         return render(request, 'collections/objects_list.html', context)
 
+    elif request.method == 'POST':
+        structure_name = request.POST.get('structure-name')
+        structure_smiles = request.POST.get('structure-smiles')
+        structure_description = request.POST.get('structure-description')
+
+        cs = current_compound.add_structure(structure_smiles, structure_name, structure_description)
+
+        return redirect(cs.url)
+
+    else:
+        return HttpResponseBadRequest()
 
 # https://envipath.org/package/<id>/compound/<id>/structure/<id>
 def package_compound_structure(request, package_uuid, compound_uuid, structure_uuid):
     current_user = _anonymous_or_real(request)
     current_package = PackageManager.get_package_by_id(current_user, package_uuid)
     current_compound = Compound.objects.get(package=current_package, uuid=compound_uuid)
-    current_structure = CompoundStructure.get(compound=current_compound, uuid=structure_uuid)
+    current_structure = CompoundStructure.objects.get(compound=current_compound, uuid=structure_uuid)
 
     if request.method == 'GET':
         context = get_base_context(request)
@@ -818,6 +831,8 @@ def package_rules(request, package_uuid):
         r = Rule.create(current_package, rule_type, name=rule_name, description=rule_description, **params)
         return redirect(r.url)
 
+    else:
+        return HttpResponseBadRequest()
 
 # https://envipath.org/package/<id>/rule/<id>
 def package_rule(request, package_uuid, rule_uuid):

templates/actions/objects/compound.html

@@ -2,6 +2,10 @@
     <a role="button" data-toggle="modal" data-target="#edit_compound_modal">
         <i class="glyphicon glyphicon-edit"></i> Edit Compound</a>
 </li>
+<li>
+    <a role="button" data-toggle="modal" data-target="#add_structure_modal">
+        <i class="glyphicon glyphicon-plus"></i> Add Structure</a>
+</li>
 <li>
     <a class="button" data-toggle="modal" data-target="#delete_compound_modal">
         <i class="glyphicon glyphicon-trash"></i> Delete Compound</a>

templates/modals/collections/new_compound_modal.html

@@ -16,12 +16,13 @@
                     <input id="compound-name" class="form-control" name="compound-name" placeholder="Name"/>
                     <label for="compound-description">Description</label>
                     <input id="compound-description" class="form-control" name="compound-description" placeholder="Description"/>
+                    <label for="compound-smiles">SMILES</label>
+                    <input type="text" class="form-control" name="compound-smiles" placeholder="SMILES" id="compound-smiles">
                     <p></p>
                     <div>
                         <iframe id="new_compound_ketcher" src="{% static '/js/ketcher2/ketcher.html' %}" width="100%"
                                 height="510"></iframe>
                     </div>
-                    <input type="hidden" name="compound-smiles" id="compound-smiles">
                     <p></p>
                 </form>
             </div>
@@ -35,16 +36,43 @@
 
 </div>
 <script>
+
+function newCompoundModalketcherToNewCompoundModalTextInput() {
+    $('#compound-smiles').val(this.ketcher.getSmiles());
+}
+
+$(function() {
+
+    $('#new_compound_ketcher').on('load', function() {
+        const checkKetcherReady = () => {
+            win = this.contentWindow
+            if (win.ketcher && 'editor' in win.ketcher) {
+                win.ketcher.editor.event.change.handlers.push({
+                    once: false,
+                    priority: 0,
+                    f: newCompoundModalketcherToNewCompoundModalTextInput,
+                    ketcher: win.ketcher
+                });
+            } else {
+                setTimeout(checkKetcherReady, 100);
+            }
+        };
+
+        checkKetcherReady();
+    })
+
     $(function() {
         $('#new_compound_modal_form_submit').on('click', function(e) {
             e.preventDefault();
             $(this).prop("disabled",true);
 
-        k = getKetcher('new_compound_ketcher');
-        $('#compound-smiles').val(k.getSmiles());
+
 
             // submit form
             $('#new_compound_modal_form').submit();
         });
     });
+
+});
+
 </script>

templates/modals/objects/add_structure_modal.html

@@ -0,0 +1,78 @@
+{% load static %}
+<div class="modal fade bs-modal-lg" id="add_structure_modal" tabindex="-1" aria-labelledby="add_structure_modal" aria-modal="true"
+     role="dialog">
+    <div class="modal-dialog modal-lg">
+        <div class="modal-content">
+            <div class="modal-header">
+                <button type="button" class="close" data-dismiss="modal" aria-label="Close">
+                    <span aria-hidden="true">×</span>
+                </button>
+                <h4 class="modal-title">Create a new Structure</h4>
+            </div>
+            <div class="modal-body">
+                <form id="add_structure_modal_form" accept-charset="UTF-8" action="{% url 'package compound structure list' meta.current_package.uuid compound.uuid %}" data-remote="true" method="post">
+                    {% csrf_token %}
+                    <label for="structure-name">Name</label>
+                    <input id="structure-name" class="form-control" name="structure-name" placeholder="Name"/>
+                    <label for="structure-description">Description</label>
+                    <input id="structure-description" class="form-control" name="structure-description" placeholder="Description"/>
+                    <label for="structure-smiles">SMILES</label>
+                    <input type="text" class="form-control" name="structure-smiles" placeholder="SMILES" id="structure-smiles">
+                    <p></p>
+                    <div>
+                        <iframe id="add_structure_ketcher" src="{% static '/js/ketcher2/ketcher.html' %}" width="100%"
+                                height="510"></iframe>
+                    </div>
+                    <p></p>
+                </form>
+            </div>
+            <div class="modal-footer">
+                <button type="button" class="btn btn-secondary pull-left" data-dismiss="modal">Close
+                </button>
+                <button type="button" class="btn btn-primary" id="add_structure_modal_form_submit">Submit</button>
+            </div>
+        </div>
+    </div>
+
+</div>
+<script>
+
+function newStructureModalketcherToNewStructureModalTextInput() {
+    $('#structure-smiles').val(this.ketcher.getSmiles());
+}
+
+$(function() {
+
+    $('#add_structure_ketcher').on('load', function() {
+        const checkKetcherReady = () => {
+            win = this.contentWindow
+            if (win.ketcher && 'editor' in win.ketcher) {
+                win.ketcher.editor.event.change.handlers.push({
+                    once: false,
+                    priority: 0,
+                    f: newStructureModalketcherToNewStructureModalTextInput,
+                    ketcher: win.ketcher
+                });
+            } else {
+                setTimeout(checkKetcherReady, 100);
+            }
+        };
+
+        checkKetcherReady();
+    })
+
+    $(function() {
+        $('#add_structure_modal_form_submit').on('click', function(e) {
+            e.preventDefault();
+            $(this).prop("disabled",true);
+
+
+
+            // submit form
+            $('#add_structure_modal_form').submit();
+        });
+    });
+
+});
+
+</script>

templates/objects/compound.html

@@ -4,6 +4,7 @@
 
 {% block action_modals %}
 {% include "modals/objects/edit_compound_modal.html" %}
+{% include "modals/objects/add_structure_modal.html" %}
 {% include "modals/objects/delete_compound_modal.html" %}
 {% endblock action_modals %}
 
@@ -71,7 +72,20 @@
             </div>
         </div>
 
-        <!-- SMILES -->
+        <!-- Canonical SMILES -->
+        <div class="panel panel-default panel-heading list-group-item" style="background-color:silver">
+            <h4 class="panel-title">
+                <a id="compound-canonical-smiles-link" data-toggle="collapse" data-parent="#compound-detail"
+                   href="#compound-canonical-smiles">Canonical SMILES Representation</a>
+            </h4>
+        </div>
+        <div id="compound-canonical-smiles" class="panel-collapse collapse in">
+            <div class="panel-body list-group-item">
+                {{ compound.default_structure.canonical_smiles }}
+            </div>
+        </div>
+
+        <!-- InChiKey -->
         <div class="panel panel-default panel-heading list-group-item" style="background-color:silver">
             <h4 class="panel-title">
                 <a id="compound-inchi-link" data-toggle="collapse" data-parent="#compound-detail"
@@ -84,10 +98,35 @@
             </div>
         </div>
 
-
         <!-- Reactions -->
+        <div class="panel panel-default panel-heading list-group-item" style="background-color:silver">
+            <h4 class="panel-title">
+                <a id="compound-reaction-link" data-toggle="collapse" data-parent="#compound-detail"
+                   href="#compound-reaction">Reactions</a>
+            </h4>
+        </div>
+        <div id="compound-reaction" class="panel-collapse collapse in">
+            <div class="panel-body list-group-item">
+                {% for r in compound.related_reactions %}
+                <a class="list-group-item" href="{{ r.url }}">{{ r.name }} <i>({{ r.package.name }})</i></a>
+                {% endfor %}
+            </div>
+        </div>
 
         <!-- Pathways -->
+        <div class="panel panel-default panel-heading list-group-item" style="background-color:silver">
+            <h4 class="panel-title">
+                <a id="compound-pathway-link" data-toggle="collapse" data-parent="#compound-detail"
+                   href="#compound-pathway">Pathways</a>
+            </h4>
+        </div>
+        <div id="compound-pathway" class="panel-collapse collapse in">
+            <div class="panel-body list-group-item">
+                {% for r in compound.related_pathways %}
+                <a class="list-group-item" href="{{ r.url }}">{{ r.name }} <i>({{ r.package.name }})</i></a>
+                {% endfor %}
+            </div>
+        </div>
 
         <!-- External Identifiers -->
 

tests/test_compound_model.py

@@ -0,0 +1,196 @@
+from django.test import TestCase
+
+from epdb.logic import PackageManager
+from epdb.models import Compound, User, CompoundStructure
+
+
+class CompoundTest(TestCase):
+    fixtures = ["test_fixture.json.gz"]
+
+    def setUp(self):
+        pass
+
+    @classmethod
+    def setUpClass(cls):
+        super(CompoundTest, cls).setUpClass()
+        cls.user = User.objects.get(username='anonymous')
+        cls.package = PackageManager.create_package(cls.user, 'Anon Test Package', 'No Desc')
+
+    @classmethod
+    def tearDownClass(cls):
+        pass
+
+    def tearDown(self):
+        pass
+
+    def test_smoke(self):
+        c = Compound.create(
+            self.package,
+            smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+            name='Afoxolaner',
+            description='No Desc'
+        )
+
+        self.assertEqual(c.default_structure.smiles,
+                         'C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F')
+        self.assertEqual(c.name, 'Afoxolaner')
+        self.assertEqual(c.description, 'No Desc')
+
+    def test_missing_smiles(self):
+        with self.assertRaises(ValueError):
+            _ = Compound.create(
+                self.package,
+                smiles=None,
+                name='Afoxolaner',
+                description='No Desc'
+            )
+
+        with self.assertRaises(ValueError):
+            _ = Compound.create(
+                self.package,
+                smiles='',
+                name='Afoxolaner',
+                description='No Desc'
+            )
+
+    def test_smiles_are_trimmed(self):
+        c = Compound.create(
+            self.package,
+            smiles='   C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F   ',
+            name='Afoxolaner',
+            description='No Desc'
+        )
+
+        self.assertEqual(c.default_structure.smiles,
+                         'C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F')
+
+    def test_name_and_description_optional(self):
+        c = Compound.create(
+            self.package,
+            smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+        )
+
+        self.assertEqual(c.name, 'no name')
+        self.assertEqual(c.description, 'no description')
+
+    def test_empty_name_and_description_are_ignored(self):
+        c = Compound.create(
+            self.package,
+            smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+            name='',
+            description='',
+        )
+
+        self.assertEqual(c.name, 'no name')
+        self.assertEqual(c.description, 'no description')
+
+    def test_deduplication(self):
+        c1 = Compound.create(
+            self.package,
+            smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+            name='Afoxolaner',
+            description='No Desc'
+        )
+
+        c2 = Compound.create(
+            self.package,
+            smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+            name='Afoxolaner',
+            description='No Desc'
+        )
+
+        # Check if create detects that this Compound already exist
+        # In this case the existing object should be returned
+        self.assertEqual(c1.pk, c2.pk)
+        self.assertEqual(len(self.package.compounds), 1)
+
+    def test_wrong_smiles(self):
+        with self.assertRaises(ValueError):
+            _ = Compound.create(
+                self.package,
+                smiles='C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+                name='Afoxolaner',
+                description='No Desc'
+            )
+
+    def test_create_with_standardized_smiles(self):
+        c = Compound.create(
+            self.package,
+            smiles='O=C(O)C1=CC=C([N+](=O)[O-])C=C1',
+            name='Standardized SMILES',
+            description='No Desc'
+        )
+        self.assertEqual(len(c.structures.all()), 1)
+
+        cs = c.structures.all()[0]
+        self.assertEqual(cs.normalized_structure, True)
+        self.assertEqual(cs.smiles, 'O=C(O)C1=CC=C([N+](=O)[O-])C=C1')
+
+    def test_create_with_non_standardized_smiles(self):
+        c = Compound.create(
+            self.package,
+            smiles='[O-][N+](=O)c1ccc(C(=O)[O-])cc1',
+            name='Non Standardized SMILES',
+            description='No Desc'
+        )
+
+        self.assertEqual(len(c.structures.all()), 2)
+        for cs in c.structures.all():
+            if cs.normalized_structure:
+                self.assertEqual(cs.smiles, 'O=C(O)C1=CC=C([N+](=O)[O-])C=C1')
+                break
+        else:
+            # Loop finished without break, lets fail...
+            self.assertEqual(1, 2)
+
+    def test_add_structure_smoke(self):
+        c = Compound.create(
+            self.package,
+            smiles='O=C(O)C1=CC=C([N+](=O)[O-])C=C1',
+            name='Standardized SMILES',
+            description='No Desc'
+        )
+
+        c.add_structure('[O-][N+](=O)c1ccc(C(=O)[O-])cc1', 'Non Standardized SMILES')
+
+        self.assertEqual(len(c.structures.all()), 2)
+
+    def test_add_structure_with_different_normalized_smiles(self):
+        c = Compound.create(
+            self.package,
+            smiles='O=C(O)C1=CC=C([N+](=O)[O-])C=C1',
+            name='Standardized SMILES',
+            description='No Desc'
+        )
+
+        with self.assertRaises(ValueError):
+            c.add_structure(
+                'C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F',
+                'Different Standardized SMILES')
+
+    def test_delete(self):
+        c = Compound.create(
+            self.package,
+            smiles='O=C(O)C1=CC=C([N+](=O)[O-])C=C1',
+            name='Standardization Test',
+            description='No Desc'
+        )
+
+        c.delete()
+
+        self.assertEqual(Compound.objects.filter(package=self.package).count(), 0)
+        self.assertEqual(CompoundStructure.objects.filter(compound__package=self.package).count(), 0)
+
+    def test_set_as_default_structure(self):
+        c1 = Compound.create(
+            self.package,
+            smiles='O=C(O)C1=CC=C([N+](=O)[O-])C=C1',
+            name='Standardized SMILES',
+            description='No Desc'
+        )
+        default_structure = c1.default_structure
+
+        c2 = c1.add_structure('[O-][N+](=O)c1ccc(C(=O)[O-])cc1', 'Non Standardized SMILES')
+
+        c1.set_default_structure(c2)
+        self.assertNotEqual(default_structure, c2)

utilities/chem.py

@@ -70,13 +70,17 @@ class FormatConverter(object):
         return Chem.MolFromSmiles(smiles)
 
     @staticmethod
-    def to_smiles(mol):
-        return Chem.MolToSmiles(mol)
+    def to_smiles(mol, canonical=False):
+        return Chem.MolToSmiles(mol, canonical=canonical)
 
     @staticmethod
     def InChIKey(smiles):
         return Chem.MolToInchiKey(FormatConverter.from_smiles(smiles))
 
+    @staticmethod
+    def canonicalize(smiles: str):
+        return FormatConverter.to_smiles(FormatConverter.from_smiles(smiles), canonical=True)
+
     @staticmethod
     def maccs(smiles):
         mol = Chem.MolFromSmiles(smiles)

utilities/plugin.py

@@ -36,7 +36,8 @@ def ensure_plugins_installed():
         if not is_installed(package_name):
             install_wheel(wheel_path)
         else:
-            print(f"Plugin already installed: {package_name}")
+            # print(f"Plugin already installed: {package_name}")
+            pass
 
 
 def discover_plugins(_cls: Type = None) -> Dict[str, Type]: