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//
// Copyright (C) 2021 Greg Landrum
//
// @@ All Rights Reserved @@
// This file is part of the RDKit.
// The contents are covered by the terms of the BSD license
// which is included in the file license.txt, found at the root
// of the RDKit source tree.
//
// ------------------------
// Distributed with v2021.09 and previous versions
namespace defaults {
// Derived from the transforms in Sitzmann et al.
// https://doi.org/10.1007/s10822-010-9346-4
// Name SMARTS Bonds Charges
const std::vector<
std::tuple<std::string, std::string, std::string, std::string>>
defaultTautomerTransformsv1{
std::make_tuple(std::string("1,3 (thio)keto/enol f"),
std::string("[CX4!H0]-[C]=[O,S,Se,Te;X1]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,3 (thio)keto/enol r"),
std::string("[O,S,Se,Te;X2!H0]-[C]=[C]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,5 (thio)keto/enol f"),
std::string("[CX4,NX3;!H0]-[C]=[C][CH0]=[O,S,Se,Te;X1]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,5 (thio)keto/enol r"),
std::string("[O,S,Se,Te;X2!H0]-[CH0]=[C]-[C]=[C,N]"),
std::string(""), std::string("")),
std::make_tuple(std::string("aliphatic imine f"),
std::string("[CX4!H0]-[C]=[NX2]"), std::string(""),
std::string("")),
std::make_tuple(std::string("aliphatic imine r"),
std::string("[NX3!H0]-[C]=[CX3]"), std::string(""),
std::string("")),
std::make_tuple(std::string("special imine f"),
std::string("[N!H0]-[C]=[CX3R0]"), std::string(""),
std::string("")),
std::make_tuple(std::string("special imine r"),
std::string("[CX4!H0]-[c]=[n]"), std::string(""),
std::string("")),
std::make_tuple(std::string("1,3 aromatic heteroatom H shift f"),
std::string("[#7+0!H0]-[#6R1]=[O,#7X2+0]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,3 aromatic heteroatom H shift "),
std::string("[O,#7+0;!H0]-[#6R1]=[#7+0X2]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,3 heteroatom H shift"),
std::string(
"[#7+0,S,O,Se,Te;!H0]-[#7X2,#6,#15]=[#7+0,#16,#8,Se,Te]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,5 aromatic heteroatom H shift"),
std::string(
"[#7+0,#16,#8;!H0]-[#6,#7]=[#6]-[#6,#7]=[#7+0,#16,#8;H0]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,5 aromatic heteroatom H shift "),
std::string("[#7+0,#16,#8,Se,Te;!H0]-[#6,nX2]=[#6,nX2]-"
"[#6,#7X2]=[#7X2+0,S,O,Se,Te]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,5 aromatic heteroatom H shift r"),
std::string("[#7+0,S,O,Se,Te;!H0]-[#6,#7X2]=[#6,nX2]-[#"
"6,nX2]=[#7+0,#16,#8,Se,Te]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,7 aromatic heteroatom H shift f"),
std::string("[#7+0,#8,#16,Se,Te;!H0]-[#6,#7X2]=[#6,#"
"7X2]-[#6,#7X2]=[#6]-[#6,#7X2]=[#7X2+0,S,O,Se,Te,CX3]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,7 aromatic heteroatom H shift r"),
std::string("[#7+0,S,O,Se,Te,CX4;!H0]-[#6,#7X2]=[#6]-[#"
"6,#7X2]=[#6,#7X2]-[#6,#7X2]=[NX2,S,O,Se,Te]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("1,9 aromatic heteroatom H shift f"),
std::string("[#7+0,O;!H0]-[#6,#7X2]=[#6,#7X2]-[#6,#7X2]"
"=[#6,#7X2]-[#6,#7X2]=[#6,#7X2]-[#6,#7X2]=[#7+0,O]"),
std::string(""), std::string("")),
std::make_tuple(std::string("1,11 aromatic heteroatom H shift f"),
std::string("[#7+0,O;!H0]-[#6,nX2]=[#6,nX2]-[#6,nX2]=[#"
"6,nX2]-[#6,nX2]=[#6,nX2]-[#6,nX2]=[#6,nX2]"
"-[#6,nX2]=[#7X2+0,O]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("furanone f"),
std::string("[O,S,N;!H0]-[#6r5]=[#6X3r5;$([#6]([#6r5])=[#6r5])]"),
std::string(""), std::string("")),
std::make_tuple(
std::string("furanone r"),
std::string("[#6r5!H0;$([#6]([#6r5])[#6r5])]-[#6r5]=[O,S,N]"),
std::string(""), std::string("")),
std::make_tuple(std::string("keten/ynol f"),
std::string("[C!H0]=[C]=[O,S,Se,Te;X1]"),
std::string("#-"), std::string("")),
std::make_tuple(std::string("keten/ynol r"),
std::string("[O,S,Se,Te;!H0X2]-[C]#[C]"),
std::string("=="), std::string("")),
std::make_tuple(std::string("ionic nitro/aci-nitro f"),
std::string("[C!H0]-[N+;$([N][O-])]=[O]"),
std::string(""), std::string("")),
std::make_tuple(std::string("ionic nitro/aci-nitro r"),
std::string("[O!H0]-[N+;$([N][O-])]=[C]"),
std::string(""), std::string("")),
std::make_tuple(std::string("oxim/nitroso f"),
std::string("[O!H0]-[N]=[C]"), std::string(""),
std::string("")),
std::make_tuple(std::string("oxim/nitroso r"),
std::string("[C!H0]-[N]=[O]"), std::string(""),
std::string("")),
std::make_tuple(std::string("oxim/nitroso via phenol f"),
std::string("[O!H0]-[N]=[C]-[C]=[C]-[C]=[OH0]"),
std::string(""), std::string("")),
std::make_tuple(std::string("oxim/nitroso via phenol r"),
std::string("[O!H0]-[c]=[c]-[c]=[c]-[N]=[OH0]"),
std::string(""), std::string("")),
std::make_tuple(std::string("cyano/iso-cyanic acid f"),
std::string("[O!H0]-[C]#[N]"), std::string("=="),
std::string("")),
std::make_tuple(std::string("cyano/iso-cyanic acid r"),
std::string("[N!H0]=[C]=[O]"), std::string("#-"),
std::string("")),
std::make_tuple(std::string("formamidinesulfinic acid f"),
std::string("[O,N;!H0]-[C]=[S,Se,Te;v6]=[O]"),
std::string("=--"), std::string("")),
std::make_tuple(std::string("formamidinesulfinic acid r"),
std::string("[O!H0]-[S,Se,Te;v4]-[C]=[O,N]"),
std::string("==-"), std::string("")),
std::make_tuple(std::string("isocyanide f"),
std::string("[C-0!H0]#[N+0]"), std::string("#"),
std::string("-+")),
std::make_tuple(std::string("isocyanide r"),
std::string("[N+!H0]#[C-]"), std::string("#"),
std::string("-+")),
std::make_tuple(std::string("phosphonic acid f"),
std::string("[OH]-[PH0]"), std::string("="),
std::string("")),
std::make_tuple(std::string("phosphonic acid r"),
std::string("[PH]=[O]"), std::string("-"),
std::string(""))};
} // namespace defaults
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