Assessment of the Potential Biological Activity of Low Molecular Weight Metabolites of Freshwater Macrophytes with QSAR

Table 1

The estimated probability () of the existence of biological activity (anti-inflammatory (AI), antifungal (AF), antibacterial (AB), and antineoplastic (AN)) of identified major components (>0.5%) of essential oil of N. lutea (NL), C. demersum (CD), and P. obtusifolius (PO); IK: Kovats retention index.

Number	Major constituents	IK	AI	AF	AB	AN	Plant
1	Hexan-2-one	790	0.697	0.421	0.317	0.557	NL
2	Hexanal	796	0.271	0.524	0.436	0.226	NL, PO, CD
3	(E)-Hex-2-en-1-ol	857	0.659	0.545	0.435	0.716	PO
4	Hexan-1-ol	865	0.659	0.447	0.33	0.532	NL, CD
5	Heptan-2-one	906	0.697	0.421	0.317	0.557	CD
6	(E)-Hept-4-enal	913	0.706	0.591	0.487	0.383	CD
7	Heptanal	915	0.271	0.524	0.436	0.226	CD
8	(2Z,4Z)-Hepta-2,4-dienal	932	0.801	0.523	0.412	0.761	CD
9	Oct-1-en-3-ol	994	0.783	0.656	0.413	0.748	CD
10	6-Methylhept-5-en-2-one	1001	0.785	0.531	0.478	0.758	CD
11	4,7,7-Trimethyl-8-oxabicyclo[2.2.2]octane; [1,8-cineol, eucalyptol]	1033	0.327	0.216	0.478	0.243	CD
12	2-Phenylacetaldehyde	1050	0.811	0.228	0.297	0.172	CD
13	(3E,5E)-Octa-3,5-dien-2-one	1104	0.881	0.584	0.445	0.772	CD
14	2,6-Dimethylcyclohexan-1-ol	1110	0.655	0.571	0.513	0.848	CD
15	2,6,6-Trimethylcyclohexa-1,3-diene-1-carbaldehyde; [safranal]	1202	0.444	0.266	0.282	0.697	CD
16	2,6,6-Trimethyl-1-cyclohexene-1-carbaldehyde; [β-cyclocitral]	1224	0.438	0.31	0.303	0.783	CD
17	6-Hydroxy-4,4-dimethyl-3H-chromen-2-one	1327	0.684	0.319	0.299	0.726	CD
18	6,10-Dimethylundecan-2-one	1422	0.657	0.512	0.372	0.546	CD
19	(E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-3-en-2-one; [α-ionone]	1437	0.565	0.588	0.495	0.717	CD
20	(5E)-6,10-Dimethylundeca-5,9-dien-2-one; [geranylacetone]	1469	0.817	0.594	0.47	0.808	CD
21	4,7-Dimethyl-1-propan-2-yl-1,2,4a,5,6,8a-hexahydronaphthalene; [α-muurolene]	1485	0.751	0.511	0.532	0.818	CD
22	(E)-4-(2,6,6-Trimethylcyclohexen-1-yl)but-3-en-2-one; [β-ionone]	1494	0.752	0.376	0.335	0.844	CD
23	4-(2-Methyl-3-oxocyclohexyl)butanal	1525	0.444	0.589	0.495	0.471	CD
24	8a-Methyl-3,4,4a,5,6,7-hexahydro-2H-naphthalene-1,8-dione	1530	0.457	0.28	0.262	0.732	CD
25	2-[(2R,4aR,8aR)-4a,8-Dimethyl-2,3,4,5,6,8a-tetrahydro-1H-naphthalen-2-yl]propan-2-ol	1536	0.69	0.462	0.449	0.624	CD
26	2-(6,10-Dimethylspiro[4.5]dec-9-en-3-yl)propan-2-ol; [agarospirol]	1604	0.598	0.282	0.467	0.449	CD
27	[2,4,4-Trimethyl-3-(2-methylpropanoyloxy)pentyl] 2-methylpropanoate	1609	0.334	0.459	0.203	0.148	CD
28	2-[(3S,5R,8S)-3,8-Dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol; [guaiol]	1638	0.672	0.31	0.379	0.760	CD
29	2-[(2R,4aS)-4a,8-Dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]propan-2-ol; [γ-eudesmol]	1639	0.738	0.331	0.42	0.731	CD
30	2-[(2R,4aR,8aS)-4a-Methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-ol; [β-eudesmol]	1659	0.869	0.524	0.52	0.879	CD
31	2-[(2R,4aR,8aR)-4a,8-Dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-ol; [α-eudesmol]	1663	0.818	0.479	0.487	0.804	CD
32	2-(4a,8-Dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)propan-2-ol; [dihydro-β-eudesmol]	1666	0.794	0.505	0.465	0.747	CD
33	2-(3,8-Dimethyl-1,2,3,3a,4,5,6,7-octahydroazulen-5-yl)propan-2-ol; [bulnesol]	1675	0.676	0.431	0.426	0.660	CD
34	Heptadecane	1700	0.583	0.378	0.31	0.316	CD
35	Pentadecanal	1732	0.271	0.524	0.436	0.226	NL, PO, CD
36	5,5-Dimethyl-2-propan-2-ylcyclohexane-1-carboxylic acid	1749	0.553	0.483	0.338	0.526	CD
37	Tetradecanoic acid	1777	0.709	0.48	0.384	0.563	NL, PO, CD
38	Octadecane	1800	0.583	0.378	0.31	0.316	CD
39	(3S,5S,8S,9S,10S,13S,14S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; [androstanol]	1839	0.794	0.587	0.455	0.858	NL
40	6,10,14-Trimethylpentadecan-2-one; [phytone]	1845	0.657	0.512	0.372	0.546	NL, PO
41	Pentadecanoic acid	1884	0.709	0.347	0.384	0.563	NL
42	(4aS,4bS,7S,10aS)-7-Ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene; [sandaracopimaradiene; pimaradiene]	1916	0.82	0.411	0.362	0.846	NL
43	4b,8,8-Trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol	1920	0.749	0.483	0.357	0.760	PO
44	Nonadecane	1926	0.583	0.378	0.31	0.316	CD
45	4,4,8a-Trimethyl-7-methylidene-8-[(2E)-3-methylpenta-2,4-dienyl]-2,3,4a,5,6,8-hexahydro-1H-naphthalene; [biformen]	1946	0.822	0.707	0.623	0.896	PO, CD
46	5α-Androstan-16-one	1958	0.786	0.437	0.339	0.860	PO
47	Dibutyl benzene-1,2-dicarboxylate; [dibutyl phthalate]	1961	0.525	0.365	0.256	0.237	NL, PO, CD
48	(E)-6-Methyl-8-(2,6,6-trimethylcyclohexen-1-yl)oct-5-en-2-one; [muquketone]	1963	0.796	0.497	0.457	0.843	PO
49	(Z)-Hexadec-11-enoic acid	1977	0.769	0.565	0.434	0.645	CD
50	Hexadecanoic acid	1987	0.709	0.48	0.384	0.563	NL, PO, CD
51	(2S,4aS)-2-Ethenyl-2,4a,8,8-tetramethyl-3,4,4b,5,6,7,10,10a-octahydro-1H-phenanthrene; [rimuen]	2035	0.878	0.52	0.361	0.850	PO
52	Kaur-16-ene; [kaurene]	2042	0.873	0.508	0.571	0.896	PO, CD
53	5-[(1S,4aS,8aS)-5,5,8a-Trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol; [manool]	2047	0.846	0.748	0.621	0.821	NL, PO, CD
54	Methyl (5E,8E,11E)-heptadeca-5,8,11-trienoate	2065	0.786	0.556	0.382	0.577	NL
55	Heneicosane	2100	0.583	0.378	0.31	0.316	PO, CD
56	(9Z,12Z)-Octadeca-9,12-dienoic acid	2146	0.829	0.574	0.443	0.653	NL
57	2-Ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate	2156	0.659	0.509	0.292	0.262	NL
58	(E,7R,11R)-3,7,11,15-Tetramethylhexadec-2-en-1-ol; [phytol]	2174	0.696	0.66	0.527	0.760	PO, CD
59	Tricosane	2300	0.583	0.378	0.31	0.316	PO
60	3α-Hydroxy-5β-pregnan-20-one; [pregnanolone]	2318	0.736	0.568	0.431	0.799	PO
61	8-(2,5,5,8A-Tetramethyl-1,4,4A,5,6,7,8,8A-octahydro-1-naphthalenyl)-6-methyl-5-octen-2-ol	2364	0.798	0.778	0.651	0.812	PO
62	5-[2-(3-Furyl)ethyl]-1,4a-dimethyl-6-methylenedecahydro-1-naphthalenecarboxylic acid	2471	0.741	0.601	0.559	0.772	PO
63	(22E)-3α-Ergosta-14,22-dien-5β-ol acetate	2740	0.742	0.418	0.281	0.887	PO

Notes: constituents with are highlighted in bold italics. Trivial and commonly accepted names of some compounds are given in square brackets.