Table 1 Key structural information for tucidinostat from DK mapping

[#6]-[CX3](-[N;H1]-[c]1:[c]:[c]:[c]:[c]:[c]1-[N;H2])=[OX1]

N-(2-aminophenyl)acetamide derivatives

Level 0

Chelating agent

Complex fragment

[nR1]1[cR1][cR1][cR1][cR1][cR1]1

Pyridines

Level 1

Carbocycles, heteroaromatic rings

[C][CX3;!$(C(=O)[*][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H1;!$(N[*][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))][C]

Secondary amides (aliphatic)/(n-aliphatic)/Defined chemical environment functional group

Level 2

Defined chemical environment functional group

[c][CX3;!$(C(=O)[*][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H1;!$(N[*][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))][c]

Secondary amides (aromatic)/(n-aromatic)

Defined chemical environment functional group

Level 2

Defined chemical environment functional group

[NX3;H2;!$(N-[N,O,S,Cl,Br,I,F]);!$(NC(=[N,O,S]))][c]

Primary amines (aromatic)

Tox Alert

Level 2

Defined chemical environment functional group

[Cl,Br,F,I][a;!r0]

X on aromatic ring

Level 2

Defined chemical environment functional group

[CX3;!$(C(=O)[*][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;!$(N[*][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]

Amides derivatives

general functional group

Level 3

general functional group

[NX3;H3,H2,H1,H0;!$(N-[N,O,S,Cl,Br,I,F]);!$(NC(=[N,O,S]))]

Amine derivatives

Level 3

general functional group

[Cl,Br,F,I][[#6];!$(C(=O)]

X derivatives

Level 3

general functional group

[CX3](=[A])(-[*!X1])-[*!X1]

Aliphatic tertiary C(sp2)

Level 4

Pharmacophoric points

[cH0]

Substituted benzene C(sp2)

Level 4

Pharmacophoric points

[c]

Aromatic C(sp2)

Level 4

Pharmacophoric points

[!H0;#7,#8,#9]

Donor atoms for H-bonds (N and O)

Level 4

Pharmacophoric points

[!$([#6,F,Cl,Br,I,o,s,nX3,#7v5,#15v5,#16v4,#16v6,* + 1,* + 2,* + 3])]

Acceptor atoms for H-bonds (N,O,F)

Level 4

Pharmacophoric points