CSEARCH Evaluation Report

Automatic Evaluation Report from CSEARCH
created on 2021-04-27 at 09:40:30
based on 340,554 reference spectra

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The CSEARCH-databases used for the evaluation of your requests
will be expanded by 15,000 entries per year !

Request from: [email protected]

Compound: 5-O-FERUOYLQUINIC-ACID_COMPOUND-5

Project: MOLECULES,19,3973[2014]CSEARCH-NUMBER:UWBT014512-20150808

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: 5-O-FERUOYLQUINIC-ACID_COMPOUND-5

Project: MOLECULES,19,3973[2014]CSEARCH-NUMBER:UWBT014512-20150808

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme

Molecular formula is: C₁₇H₂₀O₉ Molecular weight is: 368.35 amu
INCHIKEY is: RAGZUCNPTLULOL-LWOZFZEPBP

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 73.41 S -

2 173.57 S -

3 33.39 T -

4 67.63 D -

5 64.96 D -

6 71.06 D -

7 48.66 T -

8 161.50 S -

9 115.86 D -

10 145.66 D -

11 121.38 S -

12 113.91 D -

13 165.18 S -

14 51.83 Q -

15 148.53 S -

16 114.59 D -

17 116.69 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 138,184,003 compounds )

Skeleton-match found at Emolecules - 4,400,967 Compounds searched

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 C₁₇H₂₀O₉

Search CHEMSPIDER for the molecular formula C₁₇H₂₀O₉

(Description)

Basic Evaluation: Checking Multiplicities

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

From structure	17	6	8	2	1	8	9	0
From spectrum	17	6	8	2	1	8	9	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	75.8	76.1	76.1	73.4	2.7	Assigned by author Check assignment - maybe 64.96 ?	Inconsistent assignments in reference material
2	177.3	177.4	177.4	173.6	3.8	Assigned by author	Inconsistent assignments in reference material
3	40.4	38.2	38.2	33.4	4.9	Assigned by author	Inconsistent assignments in reference material
4	69.2	70.9	70.9	67.6	3.3	Assigned by author Check assignment - maybe 71.06 ?	Inconsistent assignments in reference material
5	73.1	72.7	72.7	65.0	7.8	Assigned by author Check assignment - maybe 73.41 ?	Inconsistent assignments in reference material
6	68.9	72.1	72.1	71.1	1.0	Assigned by author Check assignment - maybe 67.63 ?	Inconsistent assignments in reference material
7	36.9	38.3	38.3	48.7	10.3	Assigned by author	Inconsistent assignments in reference material
8	168.1	167.9	167.9	161.5	6.4	Assigned by author Check assignment - maybe 165.18 ?	Inconsistent assignments in reference material
9	117.9	115.4	115.4	115.9	0.4	Assigned by author Check assignment - maybe 114.59 ?	Inconsistent assignments in reference material
10	146.6	146.2	146.2	145.7	0.6	Assigned by author
11	127.3	127.3	127.3	121.4	5.9	Assigned by author Check assignment - maybe 116.69 ?	Inconsistent assignments in reference material
12	111.7	111.7	111.7	113.9	2.2	Assigned by author	Inconsistent assignments in reference material
13	148.8	148.9	148.9	165.2	16.3	Assigned by author Check assignment - maybe 148.53 ?	Inconsistent assignments in reference material
14	56.8	56.2	56.2	51.8	4.4	Assigned by author	Inconsistent assignments in reference material
15	150.0	149.3	149.3	148.5	0.8	Assigned by author Check assignment - maybe 161.50 ?
16	116.1	116.0	116.0	114.6	1.5	Assigned by author Check assignment - maybe 115.86 ?
17	123.2	123.9	123.9	116.7	7.2	Assigned by author Check assignment - maybe 121.38 ?	Inconsistent assignments in reference material
Absolute Signed	5.01ppm (17) -1.20ppm (17)	4.66ppm (17) -1.23ppm (17)	4.66ppm (17) -1.23ppm (17)			4.23ppm (17) -1.23ppm (17)	Average deviation to experimental values ( Number of shift pairs used )
Structure representation by reference data over 5.0 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 4.7ppm

	Your assignment	Difference to predicted values

1 Entry found when searching CSEARCH for identical structures

(Description)

Identical structure: Entry # 1 of 1	PHYTOCHEM.,35,209(1994)
Solvent: CD3OD 17 carbons given 17 lines given 3 assigned lines 14 exchangeable shifts C₁₇H₂₀O₉
RAGZUCNPTLULOL Search Structure on WEB Availability of spectral data

No alternative structure found when searching CSEARCH for identical spectra

(Description)

Overall Impression

Major revision necessary; high probability for errors

Compound: 5-O-FERUOYLQUINIC-ACID_COMPOUND-5

Project: MOLECULES,19,3973[2014]CSEARCH-NUMBER:UWBT014512-20150808

The CSEARCH Robot Referee recommends: Major revision necessary; high probability for errors
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Deviation between experimental and predicted data is 4.7ppm

Assignment can be probably improved at 11 positions

2 Experimental shift values differ more than 10ppm from prediction

6 Carbon positions ( out of 17 ) have a severe assignment problem

Spectrum prediction - minor inconsistencies found

1 Identical structure can be found in the CSEARCH-database

Experimental values

Predicted values

Matching map

Deviation per position ( Average is 4.7ppm )

Carbons having strong stereochemical effects

Contribution of methods

HOSE NET NET&HOSE NONE

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

Your Total Usage of the CSEARCH-Robot-Referee

679 Requests have been launched by [email protected]
Year	Accept	Minor Revision	Major Revision	Reject	Only Prediction
2021	36	450	164	29

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CPU-Usage: Evaluation needed 9.123 seconds
Wolfgang.Robien(at)univie.ac.at

Carbon number	Chemical Shift Value	Multiplicity from Structure	Multiplicity from Experiment

1	73.41	S	-
2	173.57	S	-
3	33.39	T	-
4	67.63	D	-
5	64.96	D	-
6	71.06	D	-
7	48.66	T	-
8	161.50	S	-
9	115.86	D	-
10	145.66	D	-
11	121.38	S	-
12	113.91	D	-
13	165.18	S	-
14	51.83	Q	-
15	148.53	S	-
16	114.59	D	-
17	116.69	D	-

Did you know ?

The CSEARCH-databases used for the evaluation of your requests will be expanded by 15,000 entries per year !

Major revision necessary; high probability for errors

Compound: 5-O-FERUOYLQUINIC-ACID_COMPOUND-5 Project: MOLECULES,19,3973[2014]CSEARCH-NUMBER:UWBT014512-20150808

Your Total Usage of the CSEARCH-Robot-Referee

The CSEARCH-databases used for the evaluation of your requests
will be expanded by 15,000 entries per year !

Compound: 5-O-FERUOYLQUINIC-ACID_COMPOUND-5

Project: MOLECULES,19,3973[2014]CSEARCH-NUMBER:UWBT014512-20150808