Backmerge: #5935 - Unable to establish hydrogen bond connection if monomer has no free attachment points

packages/ketcher-core/src/application/editor/modes/BaseMode.ts

@@ -26,6 +26,8 @@ import { PolymerBond } from 'domain/entities/PolymerBond';
 import { ketcherProvider } from 'application/utils';
 import { DrawingEntitiesManager } from 'domain/entities/DrawingEntitiesManager';
 import { HydrogenBond } from 'domain/entities/HydrogenBond';
+import { AttachmentPointName } from 'domain/types';
+import { MACROMOLECULES_BOND_TYPES } from 'application/editor/tools/Bond';
 
 export abstract class BaseMode {
   private _pasteIsInProgress = false;
@@ -115,10 +117,7 @@ export abstract class BaseMode {
           entity.position,
           entity,
         );
-      } else if (
-        (entity instanceof PolymerBond || entity instanceof HydrogenBond) &&
-        entity.secondMonomer
-      ) {
+      } else if (entity instanceof PolymerBond && entity.secondMonomer) {
         const firstAttachmentPoint =
           entity.firstMonomer.getAttachmentPointByBond(entity);
         const secondAttachmentPoint =
@@ -138,6 +137,15 @@ export abstract class BaseMode {
             entity,
           );
         }
+      } else if (entity instanceof HydrogenBond && entity.secondMonomer) {
+        drawingEntitiesManager.finishPolymerBondCreationModelChange(
+          entity.firstMonomer,
+          entity.secondMonomer,
+          AttachmentPointName.HYDROGEN,
+          AttachmentPointName.HYDROGEN,
+          MACROMOLECULES_BOND_TYPES.HYDROGEN,
+          entity,
+        );
       }
     });
     const ketSerializer = new KetSerializer();

packages/ketcher-core/src/application/editor/tools/Bond.ts

@@ -104,7 +104,7 @@ class PolymerBond implements BaseTool {
       const startAttachmentPoint =
         selectedRenderer.monomer.startBondAttachmentPoint;
 
-      if (!startAttachmentPoint) {
+      if (!startAttachmentPoint && !this.isHydrogenBond) {
         this.editor.events.error.dispatch(
           "Selected monomer doesn't have any free attachment points",
         );
@@ -339,14 +339,32 @@ class PolymerBond implements BaseTool {
 
   private finishBondCreation(secondMonomer: BaseMonomer) {
     assert(this.bondRenderer);
-    if (!secondMonomer.hasFreeAttachmentPoint) {
+
+    if (!this.isHydrogenBond && !secondMonomer.hasFreeAttachmentPoint) {
       this.editor.events.error.dispatch(
         "Monomers don't have any connection point available",
       );
+
       return this.editor.drawingEntitiesManager.cancelPolymerBondCreation(
         this.bondRenderer.polymerBond,
       );
     }
+
+    if (
+      this.isHydrogenBond &&
+      secondMonomer.hasHydrogenBondWithMonomer(
+        this.bondRenderer?.polymerBond.firstMonomer,
+      )
+    ) {
+      this.editor.events.error.dispatch(
+        'Unable to establish multiple hydrogen bonds between two monomers',
+      );
+
+      return this.editor.drawingEntitiesManager.cancelPolymerBondCreation(
+        this.bondRenderer.polymerBond,
+      );
+    }
+
     const firstMonomerAttachmentPoint = this.isHydrogenBond
       ? AttachmentPointName.HYDROGEN
       : this.bondRenderer.polymerBond.firstMonomer.getPotentialAttachmentPointByBond(

packages/ketcher-core/src/domain/entities/BaseMonomer.ts

@@ -40,6 +40,7 @@ export abstract class BaseMonomer extends DrawingEntity {
   public attachmentPointsVisible = false;
   public monomerItem: MonomerItemType;
   public isMonomerInRnaChainRow = false;
+  public hydrogenBonds: HydrogenBond[] = [];
 
   constructor(
     monomerItem: MonomerItemType,
@@ -108,16 +109,28 @@ export abstract class BaseMonomer extends DrawingEntity {
 
   public setPotentialBond(
     attachmentPoint: string | undefined,
-    potentialBond?: PolymerBond | null,
+    potentialBond?: PolymerBond | HydrogenBond | null,
   ) {
+    if (potentialBond instanceof HydrogenBond) {
+      this.hydrogenBonds.push(potentialBond);
+
+      return;
+    }
+
     if (attachmentPoint !== undefined) {
       this.potentialAttachmentPointsToBonds[attachmentPoint] = potentialBond;
     }
   }
 
   public getAttachmentPointByBond(
-    bond: PolymerBond | MonomerToAtomBond,
+    bond: PolymerBond | MonomerToAtomBond | HydrogenBond,
   ): AttachmentPointName | undefined {
+    if (bond instanceof HydrogenBond) {
+      return this.hydrogenBonds.find((hydrogenBond) => hydrogenBond === bond)
+        ? AttachmentPointName.HYDROGEN
+        : undefined;
+    }
+
     for (const attachmentPointName in this.attachmentPointsToBonds) {
       if (this.attachmentPointsToBonds[attachmentPointName] === bond) {
         return attachmentPointName as AttachmentPointName;
@@ -206,7 +219,7 @@ export abstract class BaseMonomer extends DrawingEntity {
 
   public forEachBond(
     callback: (
-      polymerBond: PolymerBond | MonomerToAtomBond,
+      polymerBond: PolymerBond | MonomerToAtomBond | HydrogenBond,
       attachmentPointName: AttachmentPointName,
     ) => void,
   ) {
@@ -218,21 +231,42 @@ export abstract class BaseMonomer extends DrawingEntity {
         );
       }
     }
+
+    this.hydrogenBonds.forEach((hydrogenBond) => {
+      callback(hydrogenBond, AttachmentPointName.HYDROGEN);
+    });
   }
 
   public setBond(
     attachmentPointName: AttachmentPointName,
     bond: PolymerBond | MonomerToAtomBond | HydrogenBond,
   ) {
-    this.attachmentPointsToBonds[
-      bond instanceof HydrogenBond
-        ? AttachmentPointName.HYDROGEN
-        : attachmentPointName
-    ] = bond;
+    if (!(bond instanceof HydrogenBond)) {
+      this.attachmentPointsToBonds[attachmentPointName] = bond;
+
+      return;
+    }
+
+    if (!this.hydrogenBonds.includes(bond)) {
+      this.hydrogenBonds.push(bond);
+    }
   }
 
-  public unsetBond(attachmentPointName: AttachmentPointName) {
-    this.attachmentPointsToBonds[attachmentPointName] = null;
+  public unsetBond(
+    attachmentPointName?: AttachmentPointName,
+    bondToDelete?: HydrogenBond | PolymerBond,
+  ) {
+    if (bondToDelete instanceof HydrogenBond) {
+      this.hydrogenBonds = this.hydrogenBonds.filter(
+        (bond) => bond !== bondToDelete,
+      );
+
+      return;
+    }
+
+    if (attachmentPointName) {
+      this.attachmentPointsToBonds[attachmentPointName] = null;
+    }
   }
 
   public get hasBonds() {
@@ -242,7 +276,14 @@ export abstract class BaseMonomer extends DrawingEntity {
         hasBonds = true;
       }
     }
-    return hasBonds;
+
+    return hasBonds || this.hydrogenBonds.length > 0;
+  }
+
+  public hasHydrogenBondWithMonomer(monomer: BaseMonomer) {
+    return this.hydrogenBonds.find(
+      (bond) => bond.firstMonomer === monomer || bond.secondMonomer === monomer,
+    );
   }
 
   public hasPotentialBonds() {

packages/ketcher-core/src/domain/entities/DrawingEntitiesManager.ts

@@ -698,11 +698,17 @@ export class DrawingEntitiesManager {
     polymerBond.secondMonomer?.removePotentialBonds();
     polymerBond.firstMonomer.turnOffSelection();
     polymerBond.secondMonomer?.turnOffSelection();
-    if (firstMonomerAttachmentPoint) {
-      polymerBond.firstMonomer.unsetBond(firstMonomerAttachmentPoint);
+    if (firstMonomerAttachmentPoint || polymerBond instanceof HydrogenBond) {
+      polymerBond.firstMonomer.unsetBond(
+        firstMonomerAttachmentPoint,
+        polymerBond,
+      );
     }
-    if (secondMonomerAttachmentPoint) {
-      polymerBond.secondMonomer?.unsetBond(secondMonomerAttachmentPoint);
+    if (secondMonomerAttachmentPoint || polymerBond instanceof HydrogenBond) {
+      polymerBond.secondMonomer?.unsetBond(
+        secondMonomerAttachmentPoint,
+        polymerBond,
+      );
     }
   }
 

packages/ketcher-core/src/domain/entities/HydrogenBond.ts

@@ -1,11 +1,11 @@
 import { BaseRenderer } from 'application/render/renderers/BaseRenderer';
-import { SnakeModePolymerBondRenderer } from 'application/render/renderers/PolymerBondRenderer/SnakeModePolymerBondRenderer';
 import { BaseMonomer } from './BaseMonomer';
 import { BaseBond } from './BaseBond';
+import { FlexOrSequenceOrSnakeModePolymerBondRenderer } from 'domain/entities/PolymerBond';
 
 export class HydrogenBond extends BaseBond {
   public secondMonomer?: BaseMonomer;
-  public renderer?: SnakeModePolymerBondRenderer = undefined;
+  public renderer?: FlexOrSequenceOrSnakeModePolymerBondRenderer = undefined;
 
   constructor(public firstMonomer: BaseMonomer, secondMonomer?: BaseMonomer) {
     super();
@@ -21,7 +21,9 @@ export class HydrogenBond extends BaseBond {
     this.secondMonomer = monomer;
   }
 
-  public setRenderer(renderer: SnakeModePolymerBondRenderer): void {
+  public setRenderer(
+    renderer: FlexOrSequenceOrSnakeModePolymerBondRenderer,
+  ): void {
     super.setBaseRenderer(renderer as BaseRenderer);
     this.renderer = renderer;
   }

packages/ketcher-core/src/domain/entities/PolymerBond.ts

@@ -12,7 +12,7 @@ import { AttachmentPointName } from 'domain/types';
 import { BaseMonomer } from './BaseMonomer';
 import { BaseBond } from 'domain/entities/BaseBond';
 
-type FlexOrSequenceOrSnakeModePolymerBondRenderer =
+export type FlexOrSequenceOrSnakeModePolymerBondRenderer =
   | BackBoneBondSequenceRenderer
   | FlexModePolymerBondRenderer
   | PolymerBondSequenceRenderer