KEGG rPair mapping to molfile

Question

[ktsuttlemyre]

I am attempting to trace carbons though a metabolic pathway. There are inconsistencies between atom numbering in the rPair reactions and molfile formats in the KEGG database

Ex: http://www.genome.jp/dbget-bin/www_bget?RP00079

Shows the reaction between Oxaloacetate (C00036) and (S)-Malate (C00149)
http://rest.kegg.jp/get/C00036/mo l http://rest.kegg.jp/get/C00149/mol

Unfortunately the numbering of Oxaloacetate's molfile and the Entry1 in the rPair differ for no reason. However, (S)-Malate and Entry2 of the rPair are nearly identical.

How can I map the rPair to the molfile (specifically Oxaloacetate)

[soha]

Hi, I am running into the same problem.

It looks like every RPAIR is referenced to the left hand side molecule... with total disregard to mol file numbering.

Have you figured out a solution?

Thanks

[alserg]

The same problem here. Seems I have to map chemical structures used in RPAIRS to COMPOUND structures manually. I hope it won't be that hard, at least for carbon atoms.

Answer 1

[wdiwdi]

Simple to do with the Cactvs Cheminformatics Toolkit (version 3.428 and later, www,xemistry.com/academic ):

Tcl single-line script:

molfile write RP00079.rxn [reaction create KEGG:RP00079]

Python single-line script:

Molfile.Write('RP00079.rxn',Reaction('KEGG:RP00079'))

This writes out a standard MDL RXN file with full atom mapping. Structures and reaction/mapping data are extracted from the (dynamically downloaded) KEGG KCF data, not the Molfiles. Of course it is possible to do much more with the reaction data than just dumping it into a file with a few more script commands.

My experience is that it is highly advisable to use whenever possible the original data formats of sites - KCF for KEGG, ASN.1 for PubChem etc. Use tools which allow you to work with the original data. Any remote format conversion brings the risk of data loss and transformation weirdness which you cannot control, such as the atom scrambling in KEGG Molfile output.

---

$RXN
C00036_C00149
WI    pycactvs 101920141408RP00079

  1  1
$MOL
Oxaloacetate
WIpycactvs10191414082D 0   0.00000     0.00000C00036

 13 12  0  0  0  0  0  0  0  0999 V2000
   21.5736  -15.6638    0.0000 C   0  0  0  0  0  0  0  0  0  1  0  0
   22.9771  -15.6638    0.0000 C   0  0  0  0  0  0  0  0  0  2  0  0
   20.6530  -16.7130    0.0000 C   0  0  0  0  0  0  0  0  0  3  0  0
   21.0529  -14.4776    0.0000 O   0  0  0  0  0  0  0  0  0  4  0  0
   23.6787  -16.8742    0.0000 C   0  0  0  0  0  0  0  0  0  5  0  0
   19.2817  -16.4364    0.0000 O   0  0  0  0  0  0  0  0  0  6  0  0
   21.0402  -18.0393    0.0000 O   0  0  0  0  0  0  0  0  0  7  0  0
   22.9706  -18.0843    0.0000 O   0  0  0  0  0  0  0  0  0  8  0  0
   25.0057  -16.7976    0.0000 O   0  0  0  0  0  0  0  0  0  9  0  0
   23.7783  -15.3712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8285  -14.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0097  -15.6280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.1177  -18.0793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
A  001
C5a
A  002
C1b
A  003
C6a
A  004
O5a
A  005
C6a
A  006
O6a
A  007
O6a
A  008
O6a
A  009
O6a
M  END
$MOL

(S)-Malate
WIpycactvs10191414082D 0   0.00000     0.00000C00149

 15 14  0  0  1  0  0  0  0  0999 V2000
   25.0942  -18.6205    0.0000 C   0  0  1  0  0  0  0  0  0  1  0  0
   26.2953  -19.3132    0.0000 C   0  0  0  0  0  0  0  0  0  2  0  0
   23.8998  -19.3132    0.0000 C   0  0  0  0  0  0  0  0  0  3  0  0
   25.0942  -17.2355    0.0000 O   0  0  0  0  0  0  0  0  0  4  0  0
   27.4897  -18.6205    0.0000 C   0  0  0  0  0  0  0  0  0  5  0  0
   22.7052  -18.6143    0.0000 O   0  0  0  0  0  0  0  0  0  7  0  0
   23.8360  -20.8303    0.0000 O   0  0  0  0  0  0  0  0  0  6  0  0
   28.6842  -19.3132    0.0000 O   0  0  0  0  0  0  0  0  0  8  0  0
   27.4834  -17.2355    0.0000 O   0  0  0  0  0  0  0  0  0  9  0  0
   24.3420  -18.1872    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.7379  -19.9787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.8543  -19.9774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.8460  -16.8015    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7102  -17.7462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.6825  -20.1813    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  4 13  1  0  0  0  0
  6 14  1  0  0  0  0
  8 15  1  0  0  0  0
A  001
C1c
A  002
C1b
A  003
C6a
A  004
O1a
A  005
C6a
A  006
O6a
A  007
O6a
A  008
O6a
A  009
O6a
M  END

[ktsuttlemyre]

Thanks for the reply! It has been a while since I asked this question. I am finishing up another project right now and will return to this one soon. Once I can confirm your answer is correct I will select it. Until then have an upvote! Thanks!

[ktsuttlemyre]

What dependencies need to be imported when using the python line?