CSEARCH Evaluation Report

Automatic Evaluation Report from CSEARCH
created on 2021-03-09 at 14:30:30
based on 340,554 reference spectra

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Every webpage created by the CSEARCH-Robot-Referee is marked with a
digital fingerprint - editing of these webpages is therefore prohibited !
The chance to manipulate such a page successfully is like isolating
one, single molecule out of one Peta-MOL of substance !

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Compound: 1-[[1-[4-BROMOBENZYL]-1H-1,2,3-TRIAZOL-4-YL]-METHYL]-5-METHYL-PYRIMIDINE-2,4-[1

Project: MOLECULES,18,15064[2013]CSEARCH-NUMBER:UWIR009945-20141206

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: 1-[[1-[4-BROMOBENZYL]-1H-1,2,3-TRIAZOL-4-YL]-METHYL]-5-METHYL-PYRIMIDINE-2,4-[1

Project: MOLECULES,18,15064[2013]CSEARCH-NUMBER:UWIR009945-20141206

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme

Molecular formula is: C₁₅H₁₄BrN₅O₂ Molecular weight is: 376.23 amu
INCHIKEY is: OQXZKWDZNMWWRH-UHFFFAOYAG

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

1 151.30 S -

2 164.80 S -

3 109.40 S -

4 12.50 Q -

5 141.80 D -

6 42.80 T -

7 143.50 S -

8 124.30 D -

9 52.60 T -

10 135.90 S -

11 130.80 D -

12 32.20 D -

13 122.00 S -

14 32.20 D -

15 130.80 D -

The marked carbons have been fully assigned
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

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 C₁₅H₁₄BrN₅O₂

Search CHEMSPIDER for the molecular formula C₁₅H₁₄BrN₅O₂

(Description)

Basic Evaluation: Checking Multiplicities

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

From structure	15	6	6	2	1	8	7	0
From spectrum	15	6	6	2	1	8	7	0

Overall impression on compatibility of multiplicity from structure and experiment

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	152.3	151.4	151.8	151.3	0.5	Assigned by author
2	164.3	164.1	164.1	164.8	0.7	Assigned by author
3	109.3	113.4	112.6	109.4	3.2	Assigned by author	Inconsistent assignments in reference material
4	11.9	12.2	12.2	12.5	0.3	Assigned by author
5	140.4	139.7	140.1	141.8	1.7	Assigned by author Check assignment - maybe 143.50 ?
6	39.6	50.9	39.6	42.8	3.2	Assigned by author	Large Difference between NET & HOSE Only reference material with low similarity
7	141.9	142.5	142.2	143.5	1.3	Assigned by author Check assignment - maybe 141.80 ?
8	121.4	127.1	124.3	124.3	0.0	Assigned by author	Large Difference between NET & HOSE Only very few similar structures
9	50.2	53.1	52.5	52.6	0.1	Assigned by author
10	132.2	133.8	133.8	135.9	2.1	Assigned by author
11	130.7	129.6	129.6	130.8	1.2	Assigned by author
12	132.4	132.1	132.1	32.2	99.9	Assigned by author Check assignment - maybe 130.80 ?
13	122.0	121.6	121.6	122.0	0.4	Assigned by author
14	132.4	132.1	132.1	32.2	99.9	Assigned by author Check assignment - maybe 130.80 ?
15	130.7	129.6	129.6	130.8	1.2	Assigned by author
Absolute Signed	14.52ppm (15) -12.32ppm (15)	14.94ppm (15) -13.75ppm (15)	14.37ppm (15) -12.75ppm (15)			1.28ppm (15) -12.75ppm (15)	Average deviation to experimental values ( Number of shift pairs used )
Structure representation by reference data over 4.0 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

Carbons with massive contribution from stereochemistry
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 14.4ppm

	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

Reject; severe incompatibility detected

Compound: 1-[[1-[4-BROMOBENZYL]-1H-1,2,3-TRIAZOL-4-YL]-METHYL]-5-METHYL-PYRIMIDINE-2,4-[1

Project: MOLECULES,18,15064[2013]CSEARCH-NUMBER:UWIR009945-20141206

The CSEARCH Robot Referee recommends: Reject; severe incompatibility detected

NN-Prediction and HOSE-Code prediction differs significantly at 2 carbon positions

Deviation between experimental and predicted data is 14.4ppm

Assignment can be probably improved at 4 positions

2 Experimental shift values differ more than 50ppm from prediction

2 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 14.4ppm )

Carbons having strong stereochemical effects

Contribution of methods

HOSE NET NET&HOSE NONE

Overall Similarity Index is 10.4
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

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 C₁₅H₁₄BrN₅O₂

Search CHEMSPIDER for the molecular formula C₁₅H₁₄BrN₅O₂

(Description)

Your Total Usage of the CSEARCH-Robot-Referee

   3 Requests have been launched by [email protected]

  Year

  Accept

  Minor Revision

  Major Revision

  Reject

  Only Prediction

2021 3

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Page has been automatically written by CSEARCH
CPU-Usage: Evaluation needed 8.313 seconds
Wolfgang.Robien(at)univie.ac.at

Carbon number	Chemical Shift Value	Multiplicity from Structure	Multiplicity from Experiment

1	151.30	S	-
2	164.80	S	-
3	109.40	S	-
4	12.50	Q	-
5	141.80	D	-
6	42.80	T	-
7	143.50	S	-
8	124.30	D	-
9	52.60	T	-
10	135.90	S	-
11	130.80	D	-
12	32.20	D	-
13	122.00	S	-
14	32.20	D	-
15	130.80	D	-

3 Requests have been launched by [email protected]
Year	Accept	Minor Revision	Major Revision	Reject	Only Prediction
2021				3

Did you know ?

Every webpage created by the CSEARCH-Robot-Referee is marked with a digital fingerprint - editing of these webpages is therefore prohibited ! The chance to manipulate such a page successfully is like isolating one, single molecule out of one Peta-MOL of substance !

Reject; severe incompatibility detected

Compound: 1-[[1-[4-BROMOBENZYL]-1H-1,2,3-TRIAZOL-4-YL]-METHYL]-5-METHYL-PYRIMIDINE-2,4-[1 Project: MOLECULES,18,15064[2013]CSEARCH-NUMBER:UWIR009945-20141206

Your Total Usage of the CSEARCH-Robot-Referee

Every webpage created by the CSEARCH-Robot-Referee is marked with a
digital fingerprint - editing of these webpages is therefore prohibited !
The chance to manipulate such a page successfully is like isolating
one, single molecule out of one Peta-MOL of substance !

Compound: 1-[[1-[4-BROMOBENZYL]-1H-1,2,3-TRIAZOL-4-YL]-METHYL]-5-METHYL-PYRIMIDINE-2,4-[1

Project: MOLECULES,18,15064[2013]CSEARCH-NUMBER:UWIR009945-20141206