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HBD/HBA [message #1588] Fri, 08 April 2022 15:13 Go to next message
chemsandra is currently offline  chemsandra
Messages: 1
Registered: April 2022
Junior Member
I have a question about hydrogen bond donors (HBD) and hydrogen bond acceptors (HBA). I was wondering how DataWarrior software defines HBD and HBA. Is there any literature reference about this?

I used KNIME and DataWarrior to calculate the number of HBA and HBA. However, the result of using both software is different.

I would be grateful for the help with this.
Re: HBD/HBA [message #1608 is a reply to message #1588] Fri, 13 May 2022 18:06 Go to previous messageGo to next message
thomas is currently offline  thomas
Messages: 711
Registered: June 2014
Senior Member
The HBA and HBD counts in DataWarrior are very simple.
Every oxygen and nitrogen is considered an acceptor and every oxygen and nitrogen with at least an attached hydrogen is considered a donor.
Re: HBD/HBA [message #1863 is a reply to message #1608] Mon, 06 March 2023 20:59 Go to previous messageGo to next message
P_Fitz
Messages: 17
Registered: November 2019
Junior Member
Is this an accurate way to do HBA/HBD? I wouldn't consider an amide -N an H bond acceptor.
Re: HBD/HBA [message #1865 is a reply to message #1863] Mon, 06 March 2023 23:28 Go to previous messageGo to next message
nbehrnd is currently offline  nbehrnd
Messages: 224
Registered: June 2019
Senior Member
Initially for curiosity, I submitted a few simple molecules to the assignment to H-bond donors, and acceptors

/forum/index.php?t=getfile&id=675&private=0

DW assigns last entry 6, diacetamide, 3 acceptors and 1 donor. This contrasts to Etter's paper[1] with two accptors and one donor only.

/forum/index.php?t=getfile&id=676&private=0

Do follow medicinal chemistry and solid state chemistry/crystallography different conventions here?

/forum/index.php?t=getfile&id=677&private=0

With regards,

Norwid

[1] Etter, M. C. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc. Chem. Res. 1990, 23, 120-126 (DOI https://doi.org/10.1021/ar00172a005).

[2] Etter, M. C.; MacDonald, J. C.; Bernstein, J. Graph Set Analysis of Hydrogen-Bond Patterns in Organic Crystals. Acta Cryst. B 1990, 46, 256-262 (DOI
https://doi.org/10.1107/S0108768189012929)
Re: HBD/HBA [message #1866 is a reply to message #1865] Tue, 07 March 2023 09:25 Go to previous messageGo to next message
zhentg is currently offline  zhentg
Messages: 25
Registered: March 2020
Junior Member
Great that this topic is discussed.
We also found the HBA/HBD counts are different from those provided by PubChem(calculated by CACTVS).
Interestingly, RDkit HBA/HBD counts seems to be similar to DW.

It will be great if the CACTVS HBA/HBD count algrithm be adapted in DW.


Datawarrior is a good tool
Re: HBD/HBA [message #1874 is a reply to message #1866] Sat, 18 March 2023 17:25 Go to previous message
thomas is currently offline  thomas
Messages: 711
Registered: June 2014
Senior Member
Admittedly, DataWarrior's (or RDkit's) simple approach of calculating HBA/HBD do not really reflect the reality in some cases. They just use the method applied in Lipinsky's 'rule of five' paper. This way DataWarrior's calculated HBA/HBD values can directly be used in the 'rule of five' context.
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