diff --git a/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts
index 17e942e3ab..8495791e09 100644
--- a/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts
+++ b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts
@@ -157,4 +157,72 @@ test.describe('Rectangle Selection Tool', () => {
     await page.mouse.click(betaAlaninePosition.x, betaAlaninePosition.y);
     await takeEditorScreenshot(page);
   });
+
+  test('Group selection using `Shift+LClick`', async ({ page }) => {
+    /* 
+    Test case: #3728 - Group selection using Shift+LClick for Macromolecules editor
+    Description: Selection elements pointly
+    */
+
+    // Create 4 peptides on canvas
+    const MONOMER_NAME = 'Tza___3-thiazolylalanine';
+    const MONOMER_ALIAS = 'Tza';
+
+    const peptide1 = await addMonomerToCanvas(
+      page,
+      MONOMER_NAME,
+      MONOMER_ALIAS,
+      300,
+      300,
+      0,
+    );
+    const peptide2 = await addMonomerToCanvas(
+      page,
+      MONOMER_NAME,
+      MONOMER_ALIAS,
+      400,
+      400,
+      1,
+    );
+    const peptide3 = await addMonomerToCanvas(
+      page,
+      MONOMER_NAME,
+      MONOMER_ALIAS,
+      500,
+      500,
+      2,
+    );
+    const peptide4 = await addMonomerToCanvas(
+      page,
+      MONOMER_NAME,
+      MONOMER_ALIAS,
+      500,
+      200,
+      3,
+    );
+
+    // Select bond tool
+    await selectSingleBondTool(page);
+
+    // Create bonds between peptides
+    await bondTwoMonomers(page, peptide1, peptide2);
+    await bondTwoMonomers(page, peptide3, peptide2);
+    await bondTwoMonomers(page, peptide3, peptide4);
+
+    await takeEditorScreenshot(page);
+
+    // Select rectangle selection tool
+    await selectRectangleSelectionTool(page);
+
+    // Select monomers pointly by clicking Shift+LClick
+    await page.keyboard.down('Shift');
+
+    await page.mouse.click(300, 300);
+    await page.mouse.click(400, 400);
+    await page.mouse.click(500, 350);
+
+    await page.keyboard.up('Shift');
+
+    await takeEditorScreenshot(page);
+  });
 });
diff --git a/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-1-chromium-linux.png b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-1-chromium-linux.png
new file mode 100644
index 0000000000..73ce120816
Binary files /dev/null and b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-1-chromium-linux.png differ
diff --git a/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-2-chromium-linux.png b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-2-chromium-linux.png
new file mode 100644
index 0000000000..ef0d3232e5
Binary files /dev/null and b/ketcher-autotests/tests/Macromolecule-editor/Rectangle-Selection-Tool/rectangle-selection-tool.spec.ts-snapshots/Rectangle-Selection-Tool-Group-selection-using-Shift-LClick-2-chromium-linux.png differ
diff --git a/packages/ketcher-core/src/application/editor/tools/SelectRectangle.ts b/packages/ketcher-core/src/application/editor/tools/SelectRectangle.ts
index c4134726ea..1897b4a59c 100644
--- a/packages/ketcher-core/src/application/editor/tools/SelectRectangle.ts
+++ b/packages/ketcher-core/src/application/editor/tools/SelectRectangle.ts
@@ -101,7 +101,7 @@ class SelectRectangle implements BaseTool {
   mousedown(event) {
     const renderer = event.target.__data__;
     let modelChanges: Command;
-    if (renderer instanceof BaseRenderer) {
+    if (renderer instanceof BaseRenderer && !event.shiftKey) {
       this.moveStarted = true;
       this.mousePositionAfterMove = this.editor.lastCursorPositionOfCanvas;
       this.mousePositionBeforeMove = this.editor.lastCursorPositionOfCanvas;
@@ -112,6 +112,12 @@ class SelectRectangle implements BaseTool {
           renderer.drawingEntity,
         );
       }
+    } else if (renderer instanceof BaseRenderer && event.shiftKey) {
+      const drawingEntity = renderer.drawingEntity;
+      modelChanges =
+        this.editor.drawingEntitiesManager.selectCurrentDrawingEntities(
+          drawingEntity,
+        );
     } else {
       modelChanges =
         this.editor.drawingEntitiesManager.unselectAllDrawingEntities();
diff --git a/packages/ketcher-core/src/domain/entities/DrawingEntitiesManager.ts b/packages/ketcher-core/src/domain/entities/DrawingEntitiesManager.ts
index c315e1e5a2..de7a0945f0 100644
--- a/packages/ketcher-core/src/domain/entities/DrawingEntitiesManager.ts
+++ b/packages/ketcher-core/src/domain/entities/DrawingEntitiesManager.ts
@@ -175,6 +175,29 @@ export class DrawingEntitiesManager {
     return command;
   }
 
+  public selectCurrentDrawingEntities(drawingEntity: DrawingEntity) {
+    const command = new Command();
+
+    this.allEntities.forEach(([, drawingEntity]) => {
+      if (drawingEntity.selected) {
+        const operation = new DrawingEntitySelectOperation(drawingEntity);
+        command.addOperation(operation);
+      }
+    });
+
+    if (drawingEntity.selected) {
+      drawingEntity.turnOffSelection();
+      const operation = new DrawingEntitySelectOperation(drawingEntity);
+      command.addOperation(operation);
+    } else {
+      drawingEntity.turnOnSelection();
+      const operation = new DrawingEntitySelectOperation(drawingEntity);
+      command.addOperation(operation);
+    }
+
+    return command;
+  }
+
   public moveDrawingEntityModelChange(
     drawingEntity: DrawingEntity,
     offset?: Vec2,