mirror of
https://github.com/openbabel/openbabel.git
synced 2026-11-03 12:49:12 -06:00
Geoff Hutchison
31c21cf4a8
- Bind the molecule to a local so the OBAtom* doesn't dangle - Also fix a few null de-reference defensive tests in alias code Signed-off-by: Geoff Hutchison <geoff.hutchison@gmail.com>
402 lines
16 KiB
Python
402 lines
16 KiB
Python
r"""Test Ketcher KET (JSON) format using the OpenBabel Python bindings.
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Mirrors the structure of testcdjsonformat.py. Covers:
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- reading a single-molecule KET file
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- reading multi-molecule KET files
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- reading a reaction KET (arrow + plus -> OBReaction)
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- writing valid JSON output
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- minified -xm output option
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- SMILES <-> KET round-trip
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- KET -> KET round-trip preserving atom/bond counts and unknown sections
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Run directly while developing:
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python ../../test/testketformat.py
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"""
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import json
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import os
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import unittest
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from testbindings import pybel, PybelWrapper
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import faulthandler
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faulthandler.enable()
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filedir = os.path.join(os.path.dirname(__file__), "files", "ket")
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def _readket(name):
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"""Helper: read a KET file from test/ket/ as a list of pybel.Molecule."""
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return list(pybel.readfile("ket", os.path.join(filedir, name)))
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def _readketstring(text, opt=None):
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"""Helper: read a KET document from a string."""
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return pybel.readstring("ket", text, opt=opt)
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class TestKetFormat(PybelWrapper):
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"""Read/write/round-trip tests for the KET format."""
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# ------------------------------------------------------------------
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# Read
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# ------------------------------------------------------------------
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def test_read_single_molecule(self):
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"""Reads ethanol (C-C-O) and verifies atom/bond counts and structure."""
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mols = _readket("ethanol.ket")
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self.assertEqual(len(mols), 1)
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mol = mols[0]
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self.assertEqual(mol.OBMol.NumAtoms(), 3)
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self.assertEqual(mol.OBMol.NumBonds(), 2)
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self.assertEqual(
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sorted(a.atomicnum for a in mol.atoms), [6, 6, 8]
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)
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bond_elements = sorted(
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tuple(
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sorted(
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[
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bond.GetBeginAtom().GetAtomicNum(),
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bond.GetEndAtom().GetAtomicNum(),
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]
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)
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)
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for bond in pybel.ob.OBMolBondIter(mol.OBMol)
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)
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self.assertEqual(bond_elements, [(6, 6), (6, 8)])
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def test_rejects_unsupported_future_major_version(self):
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"""Future KET major versions fail explicitly instead of partial parsing."""
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text = json.dumps(
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{
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"ket_version": "3.0.0",
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"root": {"nodes": []},
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}
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)
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with self.assertRaises(OSError):
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_readketstring(text)
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def test_read_multi_component(self):
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"""Reads methoxide + sodium as a single OBMol with two components."""
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mols = _readket("multi.ket")
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self.assertEqual(len(mols), 1)
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mol = mols[0]
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# 1 carbon + 1 oxygen + 1 sodium = 3 atoms.
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self.assertEqual(mol.OBMol.NumAtoms(), 3)
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atoms = list(mol.atoms)
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charges = sorted(a.formalcharge for a in atoms)
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self.assertEqual(charges, [-1, 0, 1])
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self.assertIn(11, [a.atomicnum for a in atoms]) # sodium
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def test_read_reaction(self):
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"""Reads ethene + Br2 -> 1,2-dibromoethane as an OBReaction."""
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mols = _readket("reaction.ket")
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self.assertEqual(len(mols), 1)
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mol = mols[0]
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self.assertTrue(mol.OBMol.IsReaction())
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# OBReactionFacade exposes per-role component counts.
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facade = pybel.ob.OBReactionFacade(mol.OBMol)
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# 2 reactants (ethene + Br2), 1 product (1,2-dibromoethane)
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self.assertEqual(facade.NumComponents(pybel.ob.REACTANT), 2)
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self.assertEqual(facade.NumComponents(pybel.ob.PRODUCT), 1)
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# Sanity-check the product fragment has the expected element makeup.
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product = pybel.ob.OBMol()
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facade.GetComponent(product, pybel.ob.PRODUCT, 0)
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atomic_nums = sorted(
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product.GetAtom(i).GetAtomicNum()
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for i in range(1, product.NumAtoms() + 1)
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)
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self.assertEqual(atomic_nums, [6, 6, 35, 35])
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def test_read_charges(self):
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"""Formal charges round-trip through the reader."""
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mols = _readket("multi.ket")
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mol = mols[0]
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# Oxygen is -1, sodium is +1, carbon is 0.
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by_elem = {a.atomicnum: a.formalcharge for a in mol.atoms}
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self.assertEqual(by_elem[8], -1)
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self.assertEqual(by_elem[11], 1)
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self.assertEqual(by_elem[6], 0)
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# ------------------------------------------------------------------
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# Write
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# ------------------------------------------------------------------
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def test_write_is_valid_json(self):
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"""Writer emits a parseable JSON document with the expected structure."""
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mols = _readket("ethanol.ket")
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text = mols[0].write("ket")
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doc = json.loads(text)
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self.assertIn("root", doc)
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self.assertIn("nodes", doc["root"])
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self.assertIn("mol0", doc)
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self.assertEqual(doc["mol0"]["type"], "molecule")
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self.assertEqual(len(doc["mol0"]["atoms"]), 3)
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self.assertEqual(len(doc["mol0"]["bonds"]), 2)
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def test_write_atom_coordinates(self):
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"""All emitted atom locations are 3-element [x, y, z] arrays."""
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mols = _readket("ethanol.ket")
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doc = json.loads(mols[0].write("ket"))
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for atom in doc["mol0"]["atoms"]:
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self.assertIn("location", atom)
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self.assertEqual(len(atom["location"]), 3)
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def test_write_minified(self):
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"""-xm produces no embedded newlines; default is pretty-printed."""
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mols = _readket("ethanol.ket")
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minified = mols[0].write("ket", opt={"m": None})
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self.assertNotIn("\n", minified)
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pretty = mols[0].write("ket")
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self.assertIn("\n", pretty)
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def test_write_reaction_has_arrow(self):
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"""Reaction output contains exactly one arrow meta object."""
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mols = _readket("reaction.ket")
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doc = json.loads(mols[0].write("ket"))
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nodes = doc["root"]["nodes"]
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arrows = [n for n in nodes if n.get("type") == "arrow"]
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self.assertEqual(len(arrows), 1)
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# Arrow head should be to the right of arrow tail (positive x delta).
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tail, head = arrows[0]["data"]["pos"]
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self.assertGreater(head["x"], tail["x"])
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def test_write_reaction_has_pluses(self):
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"""Reaction with 2 reactants emits at least one plus between them."""
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mols = _readket("reaction.ket")
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doc = json.loads(mols[0].write("ket"))
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nodes = doc["root"]["nodes"]
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pluses = [n for n in nodes if n.get("type") == "plus"]
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# 2 reactants and 1 product => at least 1 plus (between reactants).
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self.assertGreaterEqual(len(pluses), 1)
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# ------------------------------------------------------------------
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# Round-trip
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# ------------------------------------------------------------------
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def test_smiles_to_ket_to_smiles(self):
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"""SMILES -> KET -> SMILES preserves the canonical structure."""
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mol = pybel.readstring("smi", "C(=O)CO")
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mol.make2D()
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text = mol.write("ket")
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roundtrip = pybel.readstring("ket", text)
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self.assertEqual(roundtrip.write("smi").strip(), "C(=O)CO")
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def test_ket_to_ket_preserves_atom_bond_counts(self):
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"""KET -> KET -> KET preserves atom/bond counts after each pass."""
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mol = _readket("ethanol.ket")[0]
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first = mol.write("ket")
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m2 = pybel.readstring("ket", first)
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second = m2.write("ket")
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m3 = pybel.readstring("ket", second)
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self.assertEqual(m2.OBMol.NumAtoms(), mol.OBMol.NumAtoms())
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self.assertEqual(m2.OBMol.NumBonds(), mol.OBMol.NumBonds())
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self.assertEqual(m3.OBMol.NumAtoms(), mol.OBMol.NumAtoms())
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self.assertEqual(m3.OBMol.NumBonds(), mol.OBMol.NumBonds())
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# JSON structure remains stable across re-serialization.
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self.assertEqual(json.loads(first)["mol0"]["atoms"],
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json.loads(second)["mol0"]["atoms"])
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def test_round_trip_preserves_charges(self):
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"""Round-trip through KET preserves per-atom formal charges."""
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mols = _readket("multi.ket")
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text = mols[0].write("ket")
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rt = pybel.readstring("ket", text)
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rt_charges = sorted(a.formalcharge for a in rt.atoms)
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self.assertEqual(rt_charges, [-1, 0, 1])
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def test_round_trip_preserves_explicit_zero_implicit_h_count(self):
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"""Explicit implicitHCount: 0 survives a KET round-trip."""
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text = json.dumps(
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{
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"root": {"nodes": [{"$ref": "mol0"}]},
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"mol0": {
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"type": "molecule",
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"atoms": [
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{
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"label": "N",
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"location": [0.0, 0.0, 0.0],
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"implicitHCount": 0,
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}
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],
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"bonds": [],
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},
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}
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)
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doc = json.loads(_readketstring(text).write("ket"))
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self.assertEqual(doc["mol0"]["atoms"][0]["implicitHCount"], 0)
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def test_atom_alias_is_available_as_alias_data(self):
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"""KET atom aliases are exposed through Open Babel AliasData."""
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text = json.dumps(
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{
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"root": {"nodes": [{"$ref": "mol0"}]},
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"mol0": {
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"type": "molecule",
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"atoms": [
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{
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"label": "*",
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"alias": "COOH",
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"location": [0.0, 0.0, 0.0],
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}
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],
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"bonds": [],
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},
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}
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)
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mol = _readketstring(text)
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atom = mol.atoms[0].OBAtom
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data = atom.GetData(pybel.ob.AliasDataType)
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self.assertTrue(data)
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self.assertEqual(pybel.ob.toAliasData(data).GetAlias(), "COOH")
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def test_atom_alias_expands_with_read_option(self):
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"""The -ia read option expands chemically meaningful KET atom aliases."""
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text = json.dumps(
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{
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"root": {"nodes": [{"$ref": "mol0"}]},
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"mol0": {
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"type": "molecule",
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"atoms": [
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{
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"label": "C",
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"location": [0.0, 0.0, 0.0],
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},
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{
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"label": "*",
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"alias": "COOH",
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"location": [1.0, 0.0, 0.0],
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}
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],
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"bonds": [{"type": 1, "atoms": [0, 1]}],
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},
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}
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)
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mol = _readketstring(text, opt={"a": None})
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self.assertEqual(mol.OBMol.NumAtoms(), 4)
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self.assertEqual(mol.OBMol.NumBonds(), 3)
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self.assertEqual(sorted(a.atomicnum for a in mol.atoms), [6, 6, 8, 8])
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data = mol.atoms[1].OBAtom.GetData(pybel.ob.AliasDataType)
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self.assertTrue(data)
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alias = pybel.ob.toAliasData(data)
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self.assertTrue(alias.IsExpanded())
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self.assertEqual(alias.GetAlias(), "COOH")
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def test_round_trip_preserves_reaction(self):
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"""A reaction KET stays a reaction after a round-trip."""
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mol = _readket("reaction.ket")[0]
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text = mol.write("ket")
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rt = pybel.readstring("ket", text)
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self.assertTrue(rt.OBMol.IsReaction())
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facade = pybel.ob.OBReactionFacade(rt.OBMol)
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self.assertEqual(facade.NumComponents(pybel.ob.REACTANT), 2)
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self.assertEqual(facade.NumComponents(pybel.ob.PRODUCT), 1)
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def test_round_trip_preserves_connections(self):
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"""root.connections is preserved verbatim across a round-trip."""
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mol = _readket("with_connections.ket")[0]
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text = mol.write("ket")
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doc = json.loads(text)
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self.assertIn("connections", doc["root"])
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self.assertEqual(len(doc["root"]["connections"]), 1)
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conn = doc["root"]["connections"][0]
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self.assertEqual(conn["connectionType"], "single")
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self.assertEqual(conn["endpoint1"]["monomerId"], "monomer0")
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self.assertEqual(conn["endpoint1"]["attachmentPointId"], "R1")
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self.assertEqual(conn["endpoint2"]["moleculeId"], "mol5")
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def test_round_trip_preserves_ref_name(self):
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"""Original $ref name (mol5, not mol0) survives a round-trip."""
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mol = _readket("with_connections.ket")[0]
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doc = json.loads(mol.write("ket"))
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refs = [n["$ref"] for n in doc["root"]["nodes"] if "$ref" in n]
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self.assertIn("mol5", refs)
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self.assertIn("mol5", doc)
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def test_round_trip_preserves_node_order(self):
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"""The text meta object stays between mol5 and monomer0."""
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mol = _readket("with_connections.ket")[0]
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doc = json.loads(mol.write("ket"))
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nodes = doc["root"]["nodes"]
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kinds = [
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("ref", n["$ref"]) if "$ref" in n else ("type", n.get("type"))
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for n in nodes
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]
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self.assertEqual(
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kinds, [("ref", "mol5"), ("type", "text"), ("ref", "monomer0")]
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)
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def test_sgroup_bonds_remain_local_per_molecule(self):
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"""S-group bond indices are local to their owning molecule."""
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mol = _readket("full_fidelity.ket")[0]
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doc = json.loads(mol.write("ket"))
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# mol0: 3 bonds, S-group references bonds 0 and 2.
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self.assertIn("sgroups", doc["mol0"])
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gen0 = next(s for s in doc["mol0"]["sgroups"] if s["type"] == "GEN")
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self.assertEqual(gen0["bonds"], [0, 2])
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# mol1: 1 bond, S-group references bond 0 (local!), NOT 3 (global).
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gen1 = next(s for s in doc["mol1"]["sgroups"] if s["type"] == "GEN")
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self.assertEqual(gen1["bonds"], [0])
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def test_per_component_highlight_and_properties_scope(self):
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"""Highlight and properties don't leak across components."""
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mol = _readket("full_fidelity.ket")[0]
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doc = json.loads(mol.write("ket"))
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self.assertIn("highlight", doc["mol0"])
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self.assertIn("properties", doc["mol0"])
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self.assertNotIn("highlight", doc["mol1"])
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self.assertNotIn("properties", doc["mol1"])
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def test_no_duplicate_arrow_on_reaction_round_trip(self):
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"""Original arrow is preserved; no extra synthesized one."""
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mol = _readket("reaction.ket")[0]
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doc = json.loads(mol.write("ket"))
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arrows = [n for n in doc["root"]["nodes"] if n.get("type") == "arrow"]
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self.assertEqual(len(arrows), 1)
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# Original arrow tail at x=2, head at x=5 (not the synthesized values).
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tail, head = arrows[0]["data"]["pos"]
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self.assertAlmostEqual(tail["x"], 2.0, places=2)
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self.assertAlmostEqual(head["x"], 5.0, places=2)
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def test_empty_obmol_emits_valid_empty_document(self):
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"""Writing an empty OBMol does not produce dangling refs."""
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mol = pybel.ob.OBMol()
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text = pybel.Molecule(mol).write("ket")
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doc = json.loads(text)
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self.assertEqual(doc["root"]["nodes"], [])
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# No mol* members.
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mol_members = [k for k in doc if k.startswith("mol")]
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self.assertEqual(mol_members, [])
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def test_round_trip_preserves_passthrough(self):
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"""Unknown sections (monomer / monomerTemplate / image) survive a round-trip."""
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mol = _readket("with_passthrough.ket")[0]
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text = mol.write("ket")
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doc = json.loads(text)
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# The monomer ref and its top-level object must reappear.
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node_refs = [n.get("$ref") for n in doc["root"]["nodes"] if "$ref" in n]
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self.assertIn("monomer0", node_refs)
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self.assertIn("monomer0", doc)
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self.assertEqual(doc["monomer0"]["type"], "monomer")
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# The template ref + top-level object must reappear under root.templates.
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self.assertIn("templates", doc["root"])
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template_refs = [t.get("$ref") for t in doc["root"]["templates"]]
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self.assertIn("monomerTemplate-A___Adenine", template_refs)
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self.assertIn("monomerTemplate-A___Adenine", doc)
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# The inline image meta object survives.
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images = [n for n in doc["root"]["nodes"] if n.get("type") == "image"]
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self.assertEqual(len(images), 1)
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self.assertEqual(images[0]["format"], "image/png")
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# ket_version 2.0.0 round-trips since the input requested it.
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self.assertEqual(doc.get("ket_version"), "2.0.0")
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if __name__ == "__main__":
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unittest.main()
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