PMID- 24802889
OWN - NLM
STAT- MEDLINE
DCOM- 20150202
LR  - 20140623
IS  - 1549-960X (Electronic)
IS  - 1549-9596 (Linking)
VI  - 54
IP  - 6
DP  - 2014 Jun 23
TI  - Modeling a crowdsourced definition of molecular complexity.
PG  - 1604-16
LID - 10.1021/ci5001778 [doi]
AB  - This paper brings together the concepts of molecular complexity and 
      crowdsourcing. An exercise was done at Merck where 386 chemists voted on the 
      molecular complexity (on a scale of 1-5) of 2681 molecules taken from various 
      sources: public, licensed, and in-house. The meanComplexity of a molecule is the 
      average over all votes for that molecule. As long as enough votes are cast per 
      molecule, we find meanComplexity is quite easy to model with QSAR methods using 
      only a handful of physical descriptors (e.g., number of chiral centers, number of 
      unique topological torsions, a Wiener index, etc.). The high level of 
      self-consistency of the model (cross-validated R(2)  approximately 0.88) is remarkable given 
      that our chemists do not agree with each other strongly about the complexity of 
      any given molecule. Thus, the power of crowdsourcing is clearly demonstrated in 
      this case. The meanComplexity appears to be correlated with at least one metric 
      of synthetic complexity from the literature derived in a different way and is 
      correlated with values of process mass intensity (PMI) from the literature and 
      from in-house studies. Complexity can be used to differentiate between in-house 
      programs and to follow a program over time.
FAU - Sheridan, Robert P
AU  - Sheridan RP
AD  - Structural Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 
      2000, Rahway, New Jersey 07065, United States.
FAU - Zorn, Nicolas
AU  - Zorn N
FAU - Sherer, Edward C
AU  - Sherer EC
FAU - Campeau, Louis-Charles
AU  - Campeau LC
FAU - Chang, Charlie Zhenyu
AU  - Chang CZ
FAU - Cumming, Jared
AU  - Cumming J
FAU - Maddess, Matthew L
AU  - Maddess ML
FAU - Nantermet, Philippe G
AU  - Nantermet PG
FAU - Sinz, Christopher J
AU  - Sinz CJ
FAU - O'Shea, Paul D
AU  - O'Shea PD
LA  - eng
PT  - Journal Article
DEP - 20140520
PL  - United States
TA  - J Chem Inf Model
JT  - Journal of chemical information and modeling
JID - 101230060
SB  - IM
MH  - *Crowdsourcing
MH  - Databases, Chemical
MH  - Humans
MH  - Models, Chemical
MH  - *Molecular Structure
MH  - Quantitative Structure-Activity Relationship
MH  - Stereoisomerism
EDAT- 2014/05/08 06:00
MHDA- 2015/02/03 06:00
CRDT- 2014/05/08 06:00
PHST- 2014/05/08 06:00 [entrez]
PHST- 2014/05/08 06:00 [pubmed]
PHST- 2015/02/03 06:00 [medline]
AID - 10.1021/ci5001778 [doi]
PST - ppublish
SO  - J Chem Inf Model. 2014 Jun 23;54(6):1604-16. doi: 10.1021/ci5001778. Epub 2014 
      May 20.