InChI vs IUPAC nomenclature

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3 Απρ 2012 (πριν από 5 χρόνια και 6 μήνες)

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Aspects to be aware of when using Standard InChI Daniel Lowe Unilever Centre for Molecular Science Informatics University of Cambridge

Daniel Lowe

Unilever Centre for Molecular Science Informatics

University of Cambridge

InChI
vs

IUPAC nomenclature: Aspects to be
aware of when using Standard InChI


InChI

is used for checking the correctness of
the results of name to structure


172,249 name and
InChI

pairs used for routine
regression testing


Failures arising from stereochemistry can be
distinguished from constitutional failures


Plausible interpretations of “alanine”:




InChI
=1S/C3H7NO2/c1
-
2(4)3(5)6/h2H,4H2,1H3
,(H,5,6
)


InChI
=1S/C3H7NO2/c1
-
2(4)3(5)6/h2H,4H2,1H3
,(H,5,6)/t2
-
/m0/s1








1H
-
tetrazole 2H
-
tetrazole


3H
-
tetrazole 4H
-
tetrazole













InChI=1S/CH2N4/c1
-
2
-
4
-
5
-
3
-
1/h1H
,(H,2,3,4,5
)



Not all
tautomers

are equally
important

A fixed hydrogen layer can always be
removed but cannot be
losslessly

readded


Conditions can lead to a particular tautomer being
far more representative of a compound than
another



Not all
tautomers

readily interconvert



A particular tautomer could be the reactive species

cyclo
-
tris
(
tetracarbonylosmium
) (
3
Os

Os
)

InChI
=1S/12CO.3Os/c12*1
-
2;;;


InChI
=1/12CO.3Os/c12*1
-
2;;;/rC12O12Os3/c13
-
1
-
25(2
-
14,3
-
15,4
-
16)26(5
-
17,6
-
18,7
-
19,8
-
20)27(25,9
-
21,10
-
22,11
-
23)12
-
24

(
RS
)
-
2
-
(4
-
(2
-
methylpropyl)phenyl)
propanoic

acid


InChI=1/C13H18O2/c1
-
9(2)8
-
11
-
4
-
6
-
12(7
-
5
-
11)10(3)13(14)15/h4
-
7,9
-
10H,8H2,1
-
3H3,(H,14,15)/t10
-
/
s3/f/h14H

/s1 = absolute stereochemistry

/s2 = relative stereochemistry

/s3 = racemic stereochemistry

&
1
O
&
1
&
2
N
O
C
l
C
l
O
A mixture of relative and absolute stereochemistry, and systems
with multiple groups of relative stereochemistry are not yet
supported

beta
-
cypermethrin

(4 exact structures)

Helical stereochemistry

hexahelicene

(
M
)
-
hexahelicene



(P)
-
hexahelicene


Helical stereochemistry

(S
a
)
-
6,6

-
dinitrobiphenyl
-
2,2′
-
dicarboxylic acid

Axial stereochemistry

(R
a
)
-
6,6′
-
dinitrobiphenyl
-
2,2′
-
dicarboxylic acid

Conclusions


Where useful greater specificity
than standard
InChI

can
be achieved using extra layers





InChI does not yet support all corner cases of
stereochemistry

Any Questions?

Email: daniel@nextmovesoftware.com