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STRUCTURALLY AWARE APPROACH TO THE INTERPRETATION OF VIBRATIONAL SPECTRA. Eugene Karpushkin , Yury Zhukov, Andrey Bogomolov. www.acdlabs.com. What makes “manual” IR interpretation challenging?. IR spectral signals are “volatile” due to overlap and influence of chemical environment. - PowerPoint PPT Presentation
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Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
STRUCTURALLY AWARE APPROACH
TO THE INTERPRETATIONOF VIBRATIONAL SPECTRA
Eugene Karpushkin,Yury Zhukov,
Andrey Bogomolov
www.acdlabs.com
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
What makes “manual” IR interpretation challenging?
IR spectral signals are “volatile” due to overlap and influence of chemical environment
Many different factors to take into account simultaneously
Correlation tables and charts take expert’s time and efforts
Structurally aware software required!
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
ACD/Labs is a structurally aware software
Drawn Structure
Chemicaldatabases
Systematicnaming
Spectra
Chromatograms NMR spectralprediction
Phys-chemproperty
prediction
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
What does structural awareness mean?
Easy drawing of chemical structures 2D-cleaning/3D-optimization Attaching molecule to a spectrum Fragment structure analysis
Structure/substructure DB search Reporting with structures
Peak-to-fragment assignment
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Spectrum Interpretation ChartRaw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Possible Fragments
Searching Database: Example 1Raw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Searching Database: Example 2Raw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Candidate fragments:CH3 – 9 hits; NO2 – 7 hits; aromatics - 4 hits
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Peak AnalysisRaw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Knowledge Base: classes
alkanes, alkenes, alkynes, allenes, alicyclic compounds
alcohols, ethers, aldehydes, ketones, non-carbon acids, peroxy compounds, halogen compounds
carboxylic acids, halogenides, anhydrides, carbonates, carboxylates, esters
aromatic compounds, heterocycles amides, amines, imides, imines,
nitrocompounds, other N compounds B, P, S, Se, Si compounds inorganic ions
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Knowledge Base
Knowledge BaseRaw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
ACD/Labs Fragment Object
“Atom” descriptors: * A [C,H] AnyC SatC Aryl Hal [N,O,S]Bond descriptors:Ar D Rn Ch
*
O Aryl
O*
*
*
*
Ch
Ar
Ar
Ar
Ar
Ar
Ar
N+
O
O-A
A[N,O]
H
Ar
Ar
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Powerful means selective
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment FormulationExample set:
15 chloroanhydrides
+19 aldehydes
=34 compounds
*825 wavelengths
O
R H
O
R Cl
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation:Captured Variance
O
OH
O
Br
CH3O
O
OCH3
O
Cl
Cl
CH3
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation: Scores Plot – Structure Classes
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation: Scores Plot – Structure Classes
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation: Scores Plot – Structure Classes
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation:Bi-Plot Reveals Spectral Features
1718 cm-1
1742 cm-1
1802 cm-1
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
PCA for Fragment Formulation
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Knowledge Base is Interactive
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Structure VerificationRaw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Successful Verification is… Failed One
Raw Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Assignment and ReportingRaw
Spectrum
Report
Confirmed Structure
Hit List
Peak Table
Possible Fragments
Hypothetic Structures
PeakAnalysis
DB Search
Compare
Knowledge Base
Construct
Verify
Assign
Find Repeating
More Data
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Conclusions1. Full qualitative analysis spectral interpretation tools in the same product interface
2. Authentic Fragment Object provides almost unlimited flexibility in specifying group environment
3. Advanced tool for fragmental analysis of molecules
4. Knowledge Base with about 2400 highly selective fragments
5. Facilitated IR spectral interpretation and automated structure verification
Spectroscopy • Chromatography • PhysChem • Naming • Drawing and Databasing • Enterprise Solutions
Acknowledgements
Yury Zhukov Alexey Pastutsan