Reliable and accurate prediction of basic pK $$_a$$ values in nitrogen compounds: the pK $$_a$$ shift in supramolecular systems as a case study

Alcázar, Jackson J.; Misad Saide, Alessandra C.; Campodónico, Paola R.

doi:10.1186/s13321-023-00763-3

Table 1 Experimental and predicted basic pK$_a$ values for nitrogen compounds in pharmaceutical ingredients and dyes at 25 $^{\circ }$C in aqueous solution

From: Reliable and accurate prediction of basic pK$_a$ values in nitrogen compounds: the pK$_a$ shift in supramolecular systems as a case study

ID	Nitrogenous compounds	Experimental pK$_a$	Predicted pK$_a$^a	\|Error\|	Chemaxon pK$_a$ ^b	\|Error\|	References
131	Norephedrine	9.12	9.72	0.60	8.96	0.16	[82]
132	Procaine	9.05	8.59	0.46	8.96	0.09	[82]
133	Terbutaline	8.62	8.14	0.48	9.76	1.14	[91]
134	Quinine	8.60	8.69	0.09	8.55	0.05	[91]
135	Tetracaine	8.50	8.87	0.37	8.42	0.08	[82]
136	Astemizole	8.35	8.25	0.10	9.23	0.88	[91]
137	Nicotine	8.14	8.32	0.18	8.58	0.44	[82]
138	Clozapine	7.94	7.85	0.09	8.16	0.22	[91]
139	Ampicillin	7.25	7.60	0.35	7.23	0.02	[78]
140	Ketoconazole	6.22	6.25	0.03	6.26	0.04	[91]
141	Clotrimazole	5.89	6.17	0.28	6.42	0.53	[43]
142	Benzimidazole	5.50	5.47	0.03	5.79	0.29	[67]
143	Coumarin 7	5.10	5.26	0.16	4.21	0.89	[9]
144	Abacavir	5.04	5.35	0.31	6.87	1.83	[82]
145	Fuberidazole	4.80	5.21	0.41	3.93	0.87	[51]
146	Thiabendazole	4.60	5.00	0.40	4.08	0.52	[51]
147	Carbendazim	4.50	4.98	0.48	4.28	0.22	[51]
148	Omeprazole	4.40	4.71	0.31	4.77	0.37	[91]
149	Cerivastatin	4.38	4.79	0.41	5.58	1.20	[91]
150	Ethionamide	4.37	3.89	0.48	5.00	0.63	[91]
151	Olmesartan medoxomil	4.30	4.48	0.18	3.65	0.65	[4]
152	Lamivudine	4.24	4.01	0.23	2.00	2.24	[82]
153	Picoprazole	3.50	3.78	0.28	2.89	0.61	[63]
154	2-Amino-pentamethylbodipy	3.50	3.77	0.27	0.41	3.09	[38]
155	Diazepam	3.42	3.84	0.42	2.92	0.50	[89]
156	Prodan	3.40	3.14	0.26	4.94	1.54	[21]
157	Timoprazole	3.10	3.41	0.31	2.38	0.72	[63]
158	Benzocaine	2.45	2.39	0.06	2.78	0.33	[91]
159	Metronidazole	2.38	2.65	0.27	3.03	0.65	[82]
160	Acyclovir	2.20	2.62	0.42	2.94	0.74	[82]
161	Sulfacetamide	1.75	1.58	0.17	2.14	0.39	[67]
162	7-Dimethylazacoumarin^c	1.30	0.73	0.57	3.67	2.37	[1]
163	CHEMBL1689126^c	7.00	7.07	0.07	6.54	0.46	[63]
164	CHEMBL1689112^c	6.90	6.68	0.22	5.94	0.96	[63]
165	CHEMBL47529^c	5.50	5.48	0.02	4.96	0.54	[63]
166	CHEMBL1349378^c	4.64	4.90	0.26	4.49	0.15	[63]
167	CHEMBL432733^c	4.37	4.72	0.35	7.39	3.02	[63]
168	CHEMBL271703^c	4.20	4.26	0.06	3.46	0.74	[63]
169	CHEMBL191553^c	3.20	2.89	0.31	2.80	0.40	[63]
170	CHEMBL1405150^c	2.50	2.86	0.36	3.64	1.14	[63]
			MAE_ext:	0.28	MAE_ext:	0.60

^aCalculated by Eq. 2. RMSE_ext = 0.32
^bCalculated by Chemaxon software. RMSE_ext = 1.09
^cDoes not have a common or short name. The IUPAC name is found in Additional file 1

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Table 1 Experimental and predicted basic pK\(_a\) values for nitrogen compounds in pharmaceutical ingredients and dyes at 25 \(^{\circ }\)C in aqueous solution

Journal of Cheminformatics

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