“DompeKeys”: a set of novel substructure-based descriptors for efficient chemical space mapping, development and structural interpretation of machine learning models, and indexing of large databases

Manelfi, Candida; Tazzari, Valerio; Lunghini, Filippo; Cerchia, Carmen; Fava, Anna; Pedretti, Alessandro; Stouten, Pieter F. W.; Vistoli, Giulio; Beccari, Andrea Rosario

doi:10.1186/s13321-024-00813-4

Table 3 Chemical environment of the functional groups (description levels 2 and 3)

From: “DompeKeys”: a set of novel substructure-based descriptors for efficient chemical space mapping, development and structural interpretation of machine learning models, and indexing of large databases

Functional Group	DK
Carbamate derivatives	[OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][CX3](=[OX1])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]
Carbamates (o-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]
Carbamates (o-aliphatic)/(n-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])][C]
Carbamates (o-aliphatic)/(n-aliphatic)/(n-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([C])[C]
Carbamates (o-aliphatic)/(n-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])][c]
Carbamates (o-aliphatic)/(n-aromatic)/(n-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([c])[C]
Carbamates (o-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]
Carbamates (o-aromatic)/(n-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])][C]
Carbamates (o-aromatic)/(n-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])][c]
Carbamates (o-aliphatic)/(n-aromatic)/(n-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][C])[NX3;H0;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([c])[c]
Carbamates (o-aromatic)/(n-aliphatic)/(n-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;H0;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([C])[c]
Carbamates (o-aromatic)/(n-aromatic)/(n-aromatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([c])[c]
Carbamates (o-aromatic)/(n-aliphatic)/(n-aliphatic)	[CX3](=[OX1])([OX2;!$(O[N,O,S,Cl,Br,I,F]);!$(O(C=[N,O,S])C=[N,O,S])][c])[NX3;H0;!$(N[N,O,S,Cl,Br,I,F]);!$(N(C=[N,O,S])C=[N,O,S])]([C])[C]
Primary amides (aliphatic)	[C][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H2;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]
Secondary amides (aliphatic)/(aliphatic)	[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]
Tertiary amides (aliphatic)/(aliphatic)/(aliphatic)	[C][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([C])[C]
Tertiary amides (aromatic)/(aliphatic)/(aliphatic)	[c][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([C])[C]
Tertiary amides (aliphatic)/(aliphatic)/(aromatic)	[C][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([C])[c]
Secondary amides (aliphatic)/(aromatic)	[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]
Tertiary amides (aliphatic)/(aromatic)/(aromatic)	[C][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([c])[c]
Primary amides (aromatic)	[c][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H2;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]
Secondary amides (aromatic)/(aliphatic)	[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]
Tertiary amides (aromatic)/(aliphatic)/(aromatic)	[c][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([C])[c]
Secondary amides (aromatic)/(aromatic)	[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]
Tertiary amides (aromatic)/(aromatic)/(aromatic)	[c][CX3;!$(C(=O)[][OH,SH,NH]);!$(C(=O)C(=O));!$(C(=O)(N)[O,N,S])](=[OX1])[NX3;H0;!$(N[][OH,SH,NH]);!$(N[Cl,Br,I,F,N,S,O]);!$(N(C(=[O,S,N]))[CX3](=[N,S,O]))]([c])[c]

Back to article page

ISSN: 1758-2946

Contact us

Submission enquiries: journalsubmissions@springernature.com

Journal of Cheminformatics

Contact us