#16 Q24 simple substituents

[Nina Jeliazkova]

Acids are only recognized when represented without charges , as in R-C(=O)-OH

Salts (i.e.: cis-1,2-Cyclohexanedicarboxylic acid, calcium salt, SMILES: O=C([C@H]1[C@@H](C([O-])=O)CCCC1)[O-].[Ca+2], is classified as Cramer class III; while the acid itself (cis-1,2-Cyclohexanedicarboxylic acid, SMILES code: O=C([C@H]1[C@@H](C(O)=O)CCCC1)O), is correctly classified in Cramer class I.

Salt
Q1.Normal constituent of the body No
O=C([C@H]1[C@@H](C([O-])=O)CCCC1)[O-].[Ca+2]
Q2.Contains functional groups associated with enhanced toxicity No
O=C([C@H]1[C@@H](C([O-])=O)CCCC1)[O-].[Ca+2]
Q3.Contains elements other than C,H,O,N,divalent S Yes
O=C([C@H]1[C@@H](C([O-])=O)CCCC1)[O-].[Ca+2]
Q4.Elements not listed in Q3 occurs only as a Na,K,Ca,Mg,N salt, sulphamate,
sulphonate, sulphate, hydrochloride ... Yes
O=C([C@H]1[C@@H](C([O-])=O)CCCC1)[O-].[Ca+2]

Q7.Heterocyclic No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q16.Common terpene No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q17.Readily hydrolysed to a common terpene No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q19.Open chain No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q23.Aromatic No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
>>Q24.Monocarbocyclic with simple substituents No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q25.Cyclopropane, etc. (see explanation) No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q26.Monocycloalkanone or a bicyclocompound No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q22.Common component of food No Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))
Q33.Has sufficient number of sulphonate or sulphamate groups No
Class High (Class III) Acid
[H]OC(=O)C1([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])(C(=O)[O-]))

Acid
Q1.Normal constituent of the body No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q2.Contains functional groups associated with enhanced toxicity No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q3.Contains elements other than C,H,O,N,divalent S No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q5.Simply branched aliphatic hydrocarbon or a common carbohydrate No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q6.Benzene derivative with certain substituents No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q7.Heterocyclic No O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q16.Common terpene No O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q17.Readily hydrolysed to a common terpene No
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q19.Open chain No O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q23.Aromatic No O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
>>Q24.Monocarbocyclic with simple substituents Yes
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O
Q18.One of the list (see explanation) No Class Low (Class I)
O=C([C@H]1[C@@H](C(O)=O)CCCC1)O

[Silvia Lapenna]

If you enter a simple salt (e.g. CCCC(=O)[O-][Na+]) , Toxtree does indeed make the correction to the acid, but not with the more complex example (dicarboxylic acid, calcium salt)

[Nina Jeliazkova]

This does not depend on salt/acid recognition, but on how "simple substituents" in Q24 are defined. Q24 assumes UNCHARGED substituents,

e.g. C1CCCCC1C([O-])(=O) will answer NO in Q24
while
C1CCCCC1C([O])(=O) will answer YES in Q24

The other example "CCCC(=O)[O-][Na+]" follows different path through the tree (1N,2N,3Y,4Y(7N,16N,17N,19Y,20Y,21N,18N)) and doesn't pass through Q24, hence it does not depend on Q24 definition .

Please provide rationale why / if this should be changed.

[Nina Jeliazkova]

Modify Q24 to ignore charges.