1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
|
import os
import sys
import unittest
from rdkit import Chem, RDConfig
from rdkit.Chem import rdMolHash
class TestCase(unittest.TestCase):
def setUp(self):
pass
def test1(self):
m = Chem.MolFromSmiles('C1CCCC(O)C1c1ccnc(OC)c1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.AnonymousGraph),
'***1****(*2*****2*)*1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.ElementGraph),
'COC1CC(C2CCCCC2O)CCN1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.CanonicalSmiles),
'COc1cc(C2CCCCC2O)ccn1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.MurckoScaffold),
'c1cc(C2CCCCC2)ccn1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.ExtendedMurcko),
'*c1cc(C2CCCCC2*)ccn1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.MolFormula), 'C12H17NO2')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.AtomBondCounts), '15,16')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.DegreeVector), '0,4,9,2')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.Mesomer),
'CO[C]1[CH][C](C2CCCCC2O)[CH][CH][N]1_0')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.Regioisomer),
'*O.*O*.C.C1CCCCC1.c1ccncc1')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.NetCharge), '0')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.SmallWorldIndexBR), 'B16R2')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.SmallWorldIndexBRL), 'B16R2L9')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.ArthorSubstructureOrder),
'000f001001000c000300005f000000')
def testTautomerV2(self):
m = Chem.MolFromSmiles('CCC=O')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomer), "CC[CH][O]_0_0")
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomerv2),
"[CH3]-[C]:[C]:[O]_3_0")
m = Chem.MolFromSmiles('CC=CO')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomer),
"C[CH][CH][O]_1_0")
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomerv2),
"[CH3]-[C]:[C]:[O]_3_0")
def testProtomerV2(self):
m = Chem.MolFromSmiles('CCC=O')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomProtomer), "CC[CH][O]_0")
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomProtomerv2),
"[CH3]-[C]:[C]:[O]_3")
m = Chem.MolFromSmiles('CC=CO')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomProtomer), "C[CH][CH][O]_1")
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomProtomerv2),
"[CH3]-[C]:[C]:[O]_3")
def testCxSmiles(self):
m = Chem.MolFromSmiles(
'C[C@@H](O)[C@@H](C)[C@@H](C)C[C@H](C1=CN=CN1)C1=CNC=N1 |o1:8,5,&1:1,3,r,c:11,18,t:9,15|')
self.assertEqual(rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomer),
'C[C@H]([C@@H](C)[O])[C@@H](C)CC([C]1[CH][N][CH][N]1)[C]1[CH][N][CH][N]1_3_0')
self.assertEqual(
rdMolHash.MolHash(m, rdMolHash.HashFunction.HetAtomTautomer, True),
'C[C@H](CC([C]1[CH][N][CH][N]1)[C]1[CH][N][CH][N]1)[C@@H](C)[C@H](C)[O]_3_0 |o1:1,&1:14,16|')
if __name__ == "__main__":
unittest.main()
|
