diff --git a/packages/server/src/models/relation/path.test.ts b/packages/server/src/models/relation/path.test.ts
new file mode 100644
index 000000000..e250419cd
--- /dev/null
+++ b/packages/server/src/models/relation/path.test.ts
@@ -0,0 +1,56 @@
+import "ts-jest";
+import Superclass from "./superclass";
+import Path from "./path";
+import { RelationEnums } from "@shared/enums";
+import { IRelationModel } from "./relation";
+import Synonym from "./synonym";
+
+describe("test Path for superclasses", () => {
+  let pathInstance = new Path(RelationEnums.Type.Superclass);
+  let entries: IRelationModel[] = [];
+
+  beforeAll(async () => {
+    const ab = new Superclass({ entityIds: ["A", "B"] })
+    const bc = new Superclass({ entityIds: ["B", "C"] });
+    const cd = new Superclass({ entityIds: ["C", "D"] });
+    entries = [ab, bc, cd];
+  })
+
+  test("test Path.build", async () => {
+    pathInstance.build(entries);
+    expect(Object.keys(pathInstance.trees)).toHaveLength(entries.length);
+  })
+
+  test("test existing path from A->D", () => {
+    expect(pathInstance.pathExists("A", "D")).toBeTruthy();
+  })
+
+  test("test existing path D -> A", () => {
+    expect(pathInstance.pathExists("D", "A")).toBeFalsy();
+  })
+});
+
+describe("test Path for synonyms & superclass", () => {
+  let pathInstance = new Path(RelationEnums.Type.Synonym);
+  let entries: IRelationModel[] = [];
+
+  beforeAll(async () => {
+    const ab = new Synonym({ entityIds: ["A", "B"] })
+    const bc = new Synonym({ entityIds: ["B", "C"] });
+    const cd = new Superclass({ entityIds: ["C", "D"] });
+    entries = [ab, bc, cd];
+  })
+
+  test("test Path.build", async () => {
+    pathInstance.build(entries);
+    expect(Object.keys(pathInstance.trees)).toHaveLength(2); // only two synonyms
+  })
+
+  test("test existing path from A->D", () => {
+    expect(pathInstance.pathExists("A", "D")).toBeFalsy();
+  })
+
+  test("test existing path D -> A", () => {
+    expect(pathInstance.pathExists("D", "A")).toBeFalsy();
+  })
+});
\ No newline at end of file
diff --git a/packages/server/src/models/relation/path.ts b/packages/server/src/models/relation/path.ts
new file mode 100644
index 000000000..41603f827
--- /dev/null
+++ b/packages/server/src/models/relation/path.ts
@@ -0,0 +1,59 @@
+import { RelationEnums } from "@shared/enums";
+import { IRelationModel } from "./relation";
+
+interface PathTree {
+    mainId: string;
+    ids: string[];
+}
+
+export default class Path {
+    type: RelationEnums.Type;
+    trees: Record<string, PathTree>
+
+    constructor(type: RelationEnums.Type) {
+        this.type = type;
+        this.trees = {};
+    }
+    
+
+    async build(entries: IRelationModel[]) {
+        this.trees = {};
+        for (const entry of entries.filter(e => e.type === this.type)) {
+            this.trees[entry.entityIds[0]] = {
+                mainId: entry.entityIds[0],
+                ids: entry.entityIds,
+            }
+        }
+    }
+
+    /**
+     * Tests if there exists path from entity A -> B through relations
+     * @param a 
+     * @param b 
+     */
+    pathExists(a: string, b: string): boolean {
+        if (!this.trees[a]) {
+            return false;
+        }
+
+        let start = [this.trees[a]]
+        while (start.length) {
+            const nextStart = [];
+            for (const subtree of start) {
+                for (const entityId of subtree.ids) {
+                    if (entityId === b) {
+                        return true;
+                    }
+
+                    // entry from 'entityId' -> X must exists to be added to nextStat
+                    if (entityId !== subtree.mainId && this.trees[entityId]) {
+                        nextStart.push(this.trees[entityId]);
+                    }
+                }
+            }
+            start = nextStart;
+        }
+
+        return false;
+    }
+}
\ No newline at end of file
diff --git a/packages/server/src/models/relation/relation.ts b/packages/server/src/models/relation/relation.ts
index 63e6a0431..03fc6441b 100644
--- a/packages/server/src/models/relation/relation.ts
+++ b/packages/server/src/models/relation/relation.ts
@@ -3,11 +3,12 @@ import { r as rethink, Connection, WriteResult } from "rethinkdb-ts";
 import { IEntity, Relation as RelationTypes } from "@shared/types";
 import { DbEnums, EntityEnums, RelationEnums, UserEnums } from "@shared/enums";
 import { EnumValidators } from "@shared/enums";
-import { InternalServerError, ModelNotValidError } from "@shared/types/errors";
+import { InternalServerError, ModelNotValidError, RelationAsymetricalPathExist } from "@shared/types/errors";
 import User from "@models/user/user";
 import { IRequest } from "../../custom_typings/request";
 import { nonenumerable } from "@common/decorators";
 import Entity from "@models/entity/entity";
+import Path from "./path";
 
 export interface IRelationModel extends RelationTypes.IRelation, IDbModel {
   beforeSave(request: IRequest): Promise<void>;
@@ -178,6 +179,15 @@ export default class Relation implements IRelationModel {
    * @param request
    */
   async beforeSave(request: IRequest): Promise<void> {
+    if (RelationTypes.RelationRules[this.type]?.asymmetrical) {
+      const pathHelper = new Path(this.type);
+      await pathHelper.build(await Relation.getByType(request.db.connection, this.type))
+    
+      if (pathHelper.pathExists(this.entityIds[1], this.entityIds[0])) {
+        throw new RelationAsymetricalPathExist();
+      }
+    }
+
     if (!this.entities || this.entities.length !== this.entityIds.length) {
       this.entities = await Entity.findEntitiesByIds(
         request.db.connection,
@@ -403,6 +413,15 @@ export default class Relation implements IRelationModel {
     return items;
   }
 
+  static async getByType<T extends RelationTypes.IRelation>(db: Connection, relType: RelationEnums.Type): Promise<T[]> {
+    const items: T[] = await rethink
+      .table(Relation.table)
+      .filter({ type: relType })
+      .run(db)
+
+    return items;
+  }
+
   /**
    * searches for relations with specific entity id and returns both relation ids and connected entity ids
    * @param request IRequest
diff --git a/packages/shared/types/errors.ts b/packages/shared/types/errors.ts
index d68b34c8f..0b2625277 100644
--- a/packages/shared/types/errors.ts
+++ b/packages/shared/types/errors.ts
@@ -339,6 +339,22 @@ class RelationDoesNotExist extends CustomError {
   }
 }
 
+
+/**
+ * RelationAsymetricalPathExist will be thrown when attempting to add asymetrical relation while there could already be path from A -> B
+ */
+class RelationAsymetricalPathExist extends CustomError {
+  public static code = 400;
+  public static title = "Asymetrical constraint check failed";
+  public static message = "Relation cannot be created";
+
+  static forId(id: string): RelationAsymetricalPathExist {
+    return new RelationAsymetricalPathExist(
+      RelationAsymetricalPathExist.message.replace("$1", id)
+    );
+  }
+}
+
 /**
  * DocumentDoesNotExist will be thrown when attempting to retrieve document by id, which does not exist
  */
@@ -461,6 +477,7 @@ const allErrors: Record<string, any> = {
   StatementInvalidMove,
   EmailError,
   RelationDoesNotExist,
+  RelationAsymetricalPathExist,
   DocumentDoesNotExist,
   NetworkError,
   UnsafePasswordError,
@@ -509,6 +526,7 @@ export {
   StatementInvalidMove,
   EmailError,
   RelationDoesNotExist,
+  RelationAsymetricalPathExist,
   DocumentDoesNotExist,
   NetworkError,
   UnsafePasswordError,