CSEARCH Evaluation Report

Automatic Evaluation Report from CSEARCH
created on 2021-04-27 at 06:54:30
based on 340,554 reference spectra

Did you know ?

"Structure representation by reference data over "x" shells on average" is the last line in the prediction table.
The value of "x" gives you some feeling how good your query structure is represented by the database.
In case the value of "x" is below 2.0, it is strongly recommend to contribute your own measurements !

Request from: [email protected]

Compound: [E]-4-[[6-HYDROXY-2-OXOBENZO-[D]-[1,3]-OXATHIOL-5-YLIMINO]-METHYL]-BENZONITRILE

Project: MOLECULES,20,1968[2015]CSEARCH-NUMBER:UWPA002079-20151112

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
CSEARCH	33,587 (D)	CSEARCH-Data / Wolfgang Robien
CSEARCH	39,132 (E)	CSEARCH-Data / Wolfgang Robien + NMR-Database University of Mainz
CSEARCH	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: [email protected]

Compound: [E]-4-[[6-HYDROXY-2-OXOBENZO-[D]-[1,3]-OXATHIOL-5-YLIMINO]-METHYL]-BENZONITRILE

Project: MOLECULES,20,1968[2015]CSEARCH-NUMBER:UWPA002079-20151112

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme

Molecular formula is: C₁₅H₈N₂O₃S Molecular weight is: 296.31 amu
INCHIKEY is: CRVKKKNKWHKMBN-CAOOACKPBL

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

1 169.50 S -

2 111.80 S -

3 100.10 D -

4 135.20 S -

6 113.30 D -

8 157.90 D -

9 118.40 S -

10 129.30 D -

11 132.50 D -

12 152.10 S -

13 132.50 D -

14 129.30 D -

15 113.00 S -

The marked carbons have been fully assigned
Structural diagram

The marked carbons have exchangeable assigned lines
Structural diagram

Carbon number Chemical Shift Value Exchange Flag Multiplicity from Structure Multiplicity from Experiment

5 147.30 A S -

7 139.90 A S -

Chemical shift values of exchange-group A
Structural diagram

Graphical summary of the Chemical Shift Data

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

138,184,003 Compounds searched in PUBCHEM - nothing found

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 C₁₅H₈N₂O₃S

Search CHEMSPIDER for the molecular formula C₁₅H₈N₂O₃S

(Description)

Basic Evaluation: Checking Multiplicities

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

From structure	15	8	7	0	0	8	7	0
From spectrum	15	8	7	0	0	8	7	0

Overall impression on compatibility of multiplicity from structure and experiment

Basic Evaluation: Checking Exchange Flags

Flag	Number of Shifts	Lowest Shift value	Highest Shift value	Range	Multiplicity	Comment

A	2	139.90ppm	147.30ppm	7.40ppm	S	Range is large - please check

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	171.1	169.8	170.4	169.5	0.9	Assigned by author
2	108.1	133.8	108.1	111.8	3.7	Assigned by author	Large Difference between NET & HOSE Only reference material with low similarity
3	107.3	119.0	113.1	100.1	13.0	Assigned by author Check assignment - maybe 113.00 ?	Large Difference between NET & HOSE Only reference material with low similarity Only very few similar structures
4	120.7	135.5	128.1	135.2	7.1	Assigned by author Check assignment - maybe 129.30 ?	Large Difference between NET & HOSE Only reference material with low similarity
5	150.9	156.8	153.9	147.3	6.6	Exchangeable assigned by author Check assignment - maybe 152.10 ?	Large Difference between NET & HOSE Only reference material with low similarity Only very few similar structures
6	97.8	95.9	96.9	113.3	16.4	Assigned by author Check assignment - maybe 100.10 ?	Only reference material with low similarity
7	148.5	148.4	148.5	139.9	8.6	Exchangeable assigned by author Check assignment - maybe 147.30 ?	Only reference material with low similarity Only very few similar structures
8	157.4	159.7	158.6	157.9	0.7	Assigned by author
9	139.6	133.8	136.7	118.4	18.3	Assigned by author Check assignment - maybe 135.20 ?	Large Difference between NET & HOSE Inconsistent assignments in reference material
10	128.6	129.1	129.0	129.3	0.3	Assigned by author
11	131.1	132.5	132.5	132.5	0.0	Assigned by author
12	120.2	115.4	115.4	152.1	36.7	Assigned by author Check assignment - maybe 113.30 ?	Inconsistent assignments in reference material
13	131.1	132.5	132.5	132.5	0.0	Assigned by author
14	128.6	129.1	129.0	129.3	0.3	Assigned by author
15	117.8	118.1	118.1	113.0	5.1	Assigned by author Check assignment - maybe 118.40 ?	Inconsistent assignments in reference material
Absolute Signed	7.84ppm (15) 1.57ppm (15)	9.10ppm (15) -1.83ppm (15)	7.86ppm (15) 0.75ppm (15)			1.16ppm (15) 0.75ppm (15)	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

Quality of the Spectrum Prediction

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

Comparison of Prediction Techniques

Contribution of the methods

HOSE NET NET&HOSE NONE
Structural diagram

Similarity between predicted and experimental data based on positions

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

Overall deviation between predicted and experimental data is 7.9ppm

	Your assignment	Difference to predicted values

Nothing found when searching CSEARCH for identical structures

(Description)

No alternative structure found when searching CSEARCH for identical spectra

(Description)

Overall Impression

Major revision necessary; high probability for errors

Compound: [E]-4-[[6-HYDROXY-2-OXOBENZO-[D]-[1,3]-OXATHIOL-5-YLIMINO]-METHYL]-BENZONITRILE

Project: MOLECULES,20,1968[2015]CSEARCH-NUMBER:UWPA002079-20151112

The CSEARCH Robot Referee recommends: Major revision necessary; high probability for errors
Check integrity of page via electronic fingerprint

Large ranges within linegroup having the same exchange-flag detected

NN-Prediction and HOSE-Code prediction differs significantly at 5 carbon positions

Deviation between experimental and predicted data is 7.8ppm

Assignment can be probably improved at 8 positions

3 Experimental shift values differ more than 10ppm from prediction

1 Experimental shift value differs more than 25ppm from prediction

7 Carbon positions ( out of 15 ) have a severe assignment problem

Spectrum prediction - minor inconsistencies found

Experimental values

Predicted values

Matching map

Deviation per position ( Average is 7.9ppm )

Contribution of methods

HOSE NET NET&HOSE NONE

Overall Similarity Index is 6.0
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

History of your requests for this compound

Date/Time	Result	Method	Assigned Lines	Unassigned Lines	Stereoisomer	Permanent URL	Remark	Comparison of experimental and predicted data (Evaluation only)
2021-02-25 10:17:29	Major	Evaluation	13	0	NO
2021-04-11 01:41:30	Major	Evaluation	13	0	NO
This request	Major	Evaluation	13	0

Your Total Usage of the CSEARCH-Robot-Referee

669 Requests have been launched by [email protected]
Year	Accept	Minor Revision	Major Revision	Reject	Only Prediction
2021	36	449	162	22

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CPU-Usage: Evaluation needed 8.554 seconds
Wolfgang.Robien(at)univie.ac.at

Carbon number	Chemical Shift Value	Multiplicity from Structure	Multiplicity from Experiment

1	169.50	S	-
2	111.80	S	-
3	100.10	D	-
4	135.20	S	-
6	113.30	D	-
8	157.90	D	-
9	118.40	S	-
10	129.30	D	-
11	132.50	D	-
12	152.10	S	-
13	132.50	D	-
14	129.30	D	-
15	113.00	S	-

Carbon number	Chemical Shift Value	Exchange Flag	Multiplicity from Structure	Multiplicity from Experiment

5	147.30	A	S	-
7	139.90	A	S	-

Did you know ?

Major revision necessary; high probability for errors

Compound: [E]-4-[[6-HYDROXY-2-OXOBENZO-[D]-[1,3]-OXATHIOL-5-YLIMINO]-METHYL]-BENZONITRILE Project: MOLECULES,20,1968[2015]CSEARCH-NUMBER:UWPA002079-20151112

Your Total Usage of the CSEARCH-Robot-Referee

Compound: [E]-4-[[6-HYDROXY-2-OXOBENZO-[D]-[1,3]-OXATHIOL-5-YLIMINO]-METHYL]-BENZONITRILE

Project: MOLECULES,20,1968[2015]CSEARCH-NUMBER:UWPA002079-20151112