Table 4.

Performance of Several Methods at Reproducing the Structure(s) Linking the Substrates and Products of 20 736 AMD Records^a

reaction type	depth three	depth two	depth one	annotated site
overall	88.77	88.43	79.42	78.36
C-hydroxylation	91.29	91.07	84.71	84.24
hydrolysis	86.73	86.41	75.53	75.70
N-dealkylation	90.09	89.91	81.42	81.17
reduction	82.71	82.33	70.15	68.59
aliphatic hydroxylation	92.69	92.45	86.60	86.07
aromatic hydroxylation	92.11	92.06	86.85	86.55
O-dealkylation	91.57	91.4	86.15	85.76
C-oxidation	83.39	82.61	56.69	55.07
hydrogenation	84.71	84.32	66.87	66.72
N-demethylation	88.66	88.42	80.11	79.88
O-demethylation	93.89	93.72	90.58	90.31
dehydrogenation	86.93	86.04	68.89	66.31
epoxidation	79.19	78.51	70.54	70.54
oxidation	77.41	76.24	54.08	48.69
S-oxidation	85.9	85.32	77.24	73.86
N-oxidation	88.71	87.62	80.88	80.88
ring opening	55.25	53.22	19.49	16.10
dehalogenation	62.6	58.33	43.09	29.88
dearomatization	65.29	65.08	51.45	46.49
N-deacylation	92.26	92.26	80.87	80.18
O-deacylation	97.65	97.65	90.85	90.85
aromatization	62.34	59.48	40.26	26.23
oxidative n-dealkylation	91.29	91.29	86.19	85.59
chain shortening	67.2	67.2	12.54	7.40
N-reduction	78.35	78.35	69.76	69.42
oxidative deamination	88.65	87.23	74.47	74.11
glutathionation	34.53	34.53	27.35	0.00
optical resolution	94.44	94.44	91.67	91.67
tautomerization	56.13	52.36	8.02	6.60

^aFor each reaction type, the highest performance is in bold. Any score not statistically different from the best performance is in italics (using a P-value cutoff of 0.05).