Automatic Evaluation Report from CSEARCH
created on 2021-03-10 at 05:55:32
based on 340,554 reference spectra



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Your query structure is automatically matched against the PUBCHEM-collection,
in case the structure is registered with PUBCHEM the corresponding link is given.




Request from: molecules.discard@robien.at

Compound: 5-[Z]-3-BENZYL-5-[3-HYDROXYBENZYLIDENE]-FURAN-2[5H]-ONE_COMPOUND-13

Project: MOLECULES,12,1101[2007]CSEARCH-NUMBER:UWLU057406-20110822


Database Number of Entries Owner of Database


Please cite the CSEARCH-Robot-Referee as:

N. Haider, W. Robien; https://c13nmr.at/c13robot/robot.php


 CSEARCH 
 74,997 (A) CSEARCH-Data / Wolfgang Robien
 CSEARCH 
 56,549 (B) CSEARCH-Data / Wolfgang Robien
 CSEARCH 
 28,196 (C) CSEARCH-Data / Wolfgang Robien
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 33,587 (D) CSEARCH-Data / Wolfgang Robien
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 39,132 (E) CSEARCH-Data / Wolfgang Robien + NMR-Database University of Mainz
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 26,196 (F) CSEARCH-Data / Wolfgang Robien
 CSEARCH 
 50,594 (I) Upcoming CSEARCH-Data / Wolfgang Robien
 CSEARCH 
 31,307 (L) NMRShiftDB-Data / Version February 2012

CSEARCH-Version: 9.4.0
Robot-Referee: 2017:06:10



Request from: molecules.discard@robien.at

Compound: 5-[Z]-3-BENZYL-5-[3-HYDROXYBENZYLIDENE]-FURAN-2[5H]-ONE_COMPOUND-13

Project: MOLECULES,12,1101[2007]CSEARCH-NUMBER:UWLU057406-20110822

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme






The NMR-Spectrum for this compound is available in commercial & non-commercial databases
All Spectra from NMRPREDICT, SPECINFO, NMRShiftDB, MESTRENOVA and
CSEARCH (including spectra not yet released) were screened




Structure Proposal

Structural diagram

Molecular formula is: C18H14O3     Molecular weight is: 278.31 amu

INCHIKEY is: LDJGPVSSANSPSQ-BOPFTXTBBC



Numbering Scheme derived from the drawing sequence used during the calculation

Structural diagram


The marked carbons have been fully assigned

Structural diagram


Carbon number Chemical Shift Value Multiplicity from Structure Multiplicity from Experiment

1 170.60 S -
2 132.61 S -
3 139.75 D -
4 147.54 S -
5 112.58 D -
6 134.37 S -
7 123.30 D -
8 129.90 S -
9 116.54 D -
10 156.00 D -
11 116.39 D -
12 31.66 T -
13 137.07 S -
14 128.92 D -
15 128.57 D -
16 126.97 D -
17 128.57 D -
18 128.92 D -




The marked carbons have been fully assigned

Structural diagram


Graphical summary of the Chemical Shift Data

Spectrum





Searching external databases




The NMR-Spectrum for this compound is available in commercial & non-commercial databases
All Spectra from NMRPREDICT, SPECINFO, NMRShiftDB, MESTRENOVA and
CSEARCH (including spectra not yet released) were screened


Recall this Compound from PUBCHEM ( Stereo-Match from searching 138,167,628 compounds )

4,400,967 Compounds searched in Emolecules - nothing found

Search the Internet for this compound ( Skeleton only )
Search the Internet for this compound ( Skeleton + Stereochemistry )


Search CHEMSPIDER for this compound ( Skeleton only )
Search CHEMSPIDER for this compound ( Skeleton + Stereochemistry )


Search the Internet for the molecular formula C18H14O3


Search CHEMSPIDER for the molecular formula C18H14O3



(Description)





Basic Evaluation: Checking Multiplicities



Checking lines & multiplicity Carbons/Lines Singlet Dublet Triplet Quartet Odd Even None

From structure 18 6 11 1 0 7 11 0
From spectrum 18 6 11 1 0 7 11 0


Overall impression on compatibility of multiplicity from structure and experiment

Quality bar





Evaluation based on Spectrum Prediction






Numbering Scheme

Structural diagram



Carbon Number Neural Network
Prediction		 HOSE-Code
Prediction		 Preferred Value
from both Predictions		 Experimental
values		 Difference
(Exp-Pred/ppm)		 Assignment Prediction Quality
1 171.2 169.7 170.5 170.6 0.1 Assigned by author
2 137.8 140.4 139.1 132.6 6.5 Assigned by author
Check assignment - maybe 139.75 ?		 Only reference material with low similarity
Only very few similar structures
3 130.5 125.7 128.1 139.8 11.6 Assigned by author
Check assignment - maybe 128.57 ?		 Only reference material with low similarity
4 150.7 154.2 152.5 147.5 4.9 Assigned by author Only reference material with low similarity
Only very few similar structures
5 114.5 118.7 114.5 112.6 1.9 Assigned by author
Check assignment - maybe 116.39 ?		 Only reference material with low similarity
6 137.2 130.6 133.9 134.4 0.5 Assigned by author Large Difference between NET & HOSE
Only reference material with low similarity
7 117.4 109.0 113.2 123.3 10.1 Assigned by author
Check assignment - maybe 112.58 ?		 Large Difference between NET & HOSE
Only reference material with low similarity
8 157.9 158.1 158.0 129.9 28.1 Assigned by author
Check assignment - maybe 156.00 ?
9 118.8 116.9 117.3 116.5 0.7 Assigned by author
10 130.8 129.9 130.4 156.0 25.6 Assigned by author
Check assignment - maybe 129.90 ?
11 122.0 126.9 124.4 116.4 8.0 Assigned by author
Check assignment - maybe 123.30 ?
12 37.0 31.8 34.4 31.7 2.7 Assigned by author Large Difference between NET & HOSE
Only reference material with low similarity
13 136.7 139.6 139.0 137.1 2.0 Assigned by author Only very few similar structures
14 129.0 128.8 128.8 128.9 0.1 Assigned by author
15 129.0 128.6 128.6 128.6 0.0 Assigned by author
16 126.7 127.1 127.1 127.0 0.1 Assigned by author
17 129.0 128.6 128.6 128.6 0.0 Assigned by author
18 129.0 128.8 128.8 128.9 0.1 Assigned by author
  Absolute  
Signed
   5.37ppm   (18)  
   -0.83ppm   (18)  
   6.77ppm   (18)  
   -0.17ppm   (18)  
   5.74ppm   (18)  
   -0.37ppm   (18)  

   1.03ppm   (18)  
   -0.37ppm   (18)  
Average deviation to experimental values
( Number of shift pairs used )

Structure representation by reference data over 3.2 shells on average



Visualization of the differences between predicted and experimental values

Spectrum


Quality of the Spectrum Prediction

Quality bar



Experimental Chemical Shift Values as given

Structural diagram


Experimental Chemical Shift Values using Symmetry

Structural diagram


Preferred Chemical Shift Values from both predictions

Structural diagram


Carbons with massive contribution from stereochemistry

Structural diagram


Comparison of Prediction Techniques

Spectrum


Contribution of the methods

HOSE NET NET&HOSE NONE
Structural diagram


Similarity between predicted and experimental data based on positions

Quality bar



Matching map of predicted versus experimental data

Structural diagram


Differences between predicted and experimental data in ppm

Structural diagram


Comparison of Experimental versus Predicted Chemical Shift Values

Spectrum


Overall deviation between predicted and experimental data is 5.7ppm

Quality bar



Spectrum
Spectrum
Spectrum


  Your assignment  
 Difference to predicted values 
Highlighting
Highlighting







Nothing found when searching CSEARCH for identical structures

(Description)









No alternative structure found when searching CSEARCH for identical spectra

(Description)










Overall Impression


Major revision
Quality bar



Major revision necessary; high probability for errors




Compound: 5-[Z]-3-BENZYL-5-[3-HYDROXYBENZYLIDENE]-FURAN-2[5H]-ONE_COMPOUND-13

Project: MOLECULES,12,1101[2007]CSEARCH-NUMBER:UWLU057406-20110822


Major revision


The CSEARCH Robot Referee recommends: Major revision necessary; high probability for errors

  • NN-Prediction and HOSE-Code prediction differs significantly at 3 carbon positions
  • Deviation between experimental and predicted data is 5.7ppm
  • Assignment can be probably improved at 7 positions
  • 2 Experimental shift values differ more than 10ppm from prediction
  • 2 Experimental shift values differ more than 25ppm from prediction
  • 6 Carbon positions ( out of 18 ) have a severe assignment problem
  • Spectrum prediction - minor inconsistencies found


Experimental values
Highlighting
Predicted values
Highlighting
Matching map
Highlighting
Deviation per position ( Average is 5.7ppm )
Highlighting
Carbons having strong stereochemical effects
Highlighting
Contribution of methods
HOSE NET NET&HOSE NONE
Highlighting
Overall Similarity Index is 4.3
0.0 is a "perfect match", up to approximately 3.0 it is "reasonable",
above 5.0 it is more or less "unbelievable"

  Your assignment  
 Difference to predicted values 
Highlighting
Highlighting


The NMR-Spectrum for this compound is available in commercial & non-commercial databases
All Spectra from NMRPREDICT, SPECINFO, NMRShiftDB, MESTRENOVA and
CSEARCH (including spectra not yet released) were screened


Recall this Compound from PUBCHEM ( Stereo-Match from searching 138,167,628 compounds )

4,400,967 Compounds searched in Emolecules - nothing found

Search the Internet for this compound ( Skeleton only )
Search the Internet for this compound ( Skeleton + Stereochemistry )


Search CHEMSPIDER for this compound ( Skeleton only )
Search CHEMSPIDER for this compound ( Skeleton + Stereochemistry )


Search the Internet for the molecular formula C18H14O3


Search CHEMSPIDER for the molecular formula C18H14O3



(Description)


Your Total Usage of the CSEARCH-Robot-Referee




   7 Requests have been launched by molecules.discard@robien.at   


  Year  
  Accept  
  Minor Revision  
  Major Revision  
  Reject  


  Only Prediction  

2021 2 5



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Wolfgang.Robien(at)univie.ac.at