Appendix - Design and Use of Relational Databases in Chemistry - page 181

A.4.8 Tpsa
This function computes the polar surface area of an input SMILES struc-
ture. It uses the table for tpsa fragment SMARTS and fragment partial
polar surface areas shown in Table A.3. It relies on the count _ matches
function described in Chapter 7.

Create Function gnova.tpsa(character varying)
Returns Numeric As $EOSQL$
Select sum(psa*count_matches($1,smarts)) From tpsa;
$EOSQL$ Language SQL;

Table A.3 Fragments Definitions and Partial Surface Areas

psa Smarts Description

23.79 [N0;H0;D1;v3] N#

23.85 [N+0;H1;D1;v3] [NH]=

26.02 [N+0;H2;D1;v3] [NH2]-

25.59 [N+1;H2;D1;v4] [NH2+]=

27.64 [N+1;H3;D1;v4] [NH3+]-

12.36 [N+0;H0;D2;v3] =N-

13.6 [N+0;H0;D2;v5] =N#

12.03 [N+0;H1;D2;v3;!r3] -[NH]- not in 3-ring

21.94 [N+0;H1;D2;v3;r3] -[NH]- in 3-ring

4.36 [N+1;H0;D2;v4] -[N+]#

13.97 [N+1;H1;D2;v4] -[NH+]=

16.61 [N+1;H2;D2;v4] -[NH2+]-

12.89 [n+0;H0;D2;v3] :[n]:

15.79 [n+0;H1;D2;v3] :[nH]:

3.24 [N+0;H0;D3;v3;!r3] -N(-)-

3.01 [N+0;H0;D3;v3;r3] -N(-)- in 3-ring

11.68 [N+0;H0;D3;v5] -N(=)=

3.01 [N+1;H0;D3;v4] =[N+](-)-

4.44 [N+1;H1;D3;v4] -[NH+](-)-

0 [N+1;H0;D4;v4] -[N+](-)(-)-

17.07 [O+0;H0;D1;v2] O=

23.06 [O-1;H0;D1;v1] [O-]-

9.23 [O+0;H0;D2;!r3;v2] -O- not in 3-ring

12.53 [O+0;H0;D2;r3;v2] -O- in 3-ring

13.14 [o+0;H0;D2;v2] :o:

14.14 [n+1;H1;D2;v4] :[nH+]:

20.23 [O+0;H1;D1] [OH]-

4.93 [n+0;H0;D3;$(n-*)] -[n](:):

4.41 [n+0;H0;D3;$(n(:*)(:*):*)] :[n](:):