CSEARCH Evaluation Report

Automatic Evaluation Report from CSEARCH
created on 2021-04-27 at 10:46:30
based on 340,554 reference spectra

Did you know ?

You can donate your private spectral data to the 'community'.
Either when they have been published or after
a fixed period of time - you can select a 6, 12 or 18 month delay.

Request from: molecules@robien.at

Compound: 1,8-DIHYDROXY-4,6-DIMETHOXYXANTHONE_COMPOUND-1

Project: MOLECULES,20,127[2015]CSEARCH-NUMBER:UWPA002007-20151028

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: molecules@robien.at

Compound: 1,8-DIHYDROXY-4,6-DIMETHOXYXANTHONE_COMPOUND-1

Project: MOLECULES,20,127[2015]CSEARCH-NUMBER:UWPA002007-20151028

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme

Molecular formula is: C₁₅H₁₂O₆ Molecular weight is: 288.26 amu
INCHIKEY is: GNSHHHWDGOHNPC-UHFFFAOYAX

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

1 162.80 S -

2 97.90 D -

3 167.40 D -

4 93.10 S -

5 157.70 S -

6 154.10 S -

7 139.90 D -

8 120.40 S -

9 109.30 D -

10 145.40 S -

11 108.10 S -

12 184.60 S -

13 102.80 S -

14 55.90 Q -

15 57.40 Q -

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 )

Stereo-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 C₁₅H₁₂O₆

Search CHEMSPIDER for the molecular formula C₁₅H₁₂O₆

(Description)

Basic Evaluation: Checking Multiplicities

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

From structure	15	9	4	0	2	9	6	0
From spectrum	15	9	4	0	2	9	6	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	155.3	152.5	152.5	162.8	10.3	Assigned by author Check assignment - maybe 154.10 ?	Inconsistent assignments in reference material
2	109.2	109.0	109.0	97.9	11.1	Assigned by author Check assignment - maybe 109.30 ?
3	121.2	120.4	120.4	167.4	47.0	Assigned by author Check assignment - maybe 120.40 ?
4	139.7	139.4	139.4	93.1	46.3	Assigned by author Check assignment - maybe 139.90 ?
5	144.0	146.1	146.1	157.7	11.6	Assigned by author Check assignment - maybe 145.40 ?	Inconsistent assignments in reference material
6	158.8	157.1	157.1	154.1	3.0	Assigned by author Check assignment - maybe 157.70 ?
7	92.3	92.8	92.8	139.9	47.1	Assigned by author Check assignment - maybe 93.10 ?
8	166.1	165.5	165.5	120.4	45.1	Assigned by author Check assignment - maybe 167.40 ?	Inconsistent assignments in reference material
9	97.6	97.4	97.4	109.3	11.9	Assigned by author Check assignment - maybe 97.90 ?	Inconsistent assignments in reference material
10	162.8	162.1	162.1	145.4	16.7	Assigned by author Check assignment - maybe 162.80 ?
11	103.4	102.1	102.1	108.1	6.0	Assigned by author Check assignment - maybe 102.80 ?
12	183.5	183.9	183.9	184.6	0.7	Assigned by author
13	107.8	108.0	108.0	102.8	5.2	Assigned by author Check assignment - maybe 108.10 ?
14	56.0	55.9	55.9	55.9	0.0	Assigned by author
15	56.8	57.1	57.1	57.4	0.3	Assigned by author
Absolute Signed	17.60ppm (15) 0.15ppm (15)	17.49ppm (15) 0.49ppm (15)	17.49ppm (15) 0.49ppm (15)			0.59ppm (15) 0.49ppm (15)	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

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 17.5ppm

	Your assignment	Difference to predicted values

4 Entries found when searching CSEARCH for identical structures

(Description)

Identical structure: Entry # 1 of 4	PLANTA.MED.,60,507(1994)
Solvent: CDCL3 15 carbons given 15 lines given 13 assigned lines 2 exchangeable shifts C₁₅H₁₂O₆
GNSHHHWDGOHNPC Search Structure on WEB Availability of spectral data

Identical structure: Entry # 2 of 4	PHYTOCHEM.,29,1563(1990)
Solvent: DMSO-D6:D2O 15 carbons given 15 lines given 13 assigned lines 2 exchangeable shifts C₁₅H₁₂O₆
GNSHHHWDGOHNPC Search Structure on WEB Availability of spectral data

Identical structure: Entry # 3 of 4	PHYTOCHEM.,30,1037(1991)
Solvent: C5D5N 15 carbons given 15 lines given 13 assigned lines 2 exchangeable shifts C₁₅H₁₂O₆
GNSHHHWDGOHNPC Search Structure on WEB Availability of spectral data

Identical structure: Entry # 4 of 4	J.CHEM.PHARM.RES.,2,1,125(2010)
Solvent: CDCL3 15 carbons given 15 lines given 13 assigned lines 2 exchangeable shifts C₁₅H₁₂O₆
GNSHHHWDGOHNPC Search Structure on WEB Availability of spectral data

No alternative structure found when searching CSEARCH for identical spectra

(Description)

Overall Impression

Reject; severe incompatibility detected

Compound: 1,8-DIHYDROXY-4,6-DIMETHOXYXANTHONE_COMPOUND-1

Project: MOLECULES,20,127[2015]CSEARCH-NUMBER:UWPA002007-20151028

The CSEARCH Robot Referee recommends: Reject; severe incompatibility detected
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Deviation between experimental and predicted data is 17.5ppm

Assignment can be probably improved at 12 positions

5 Experimental shift values differ more than 10ppm from prediction

4 Experimental shift values differ more than 25ppm from prediction

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

Spectrum prediction - minor inconsistencies found

4 Identical structures can be found in the CSEARCH-database

Experimental values

Predicted values

Matching map

Deviation per position ( Average is 17.5ppm )

Contribution of methods

HOSE NET NET&HOSE NONE

Overall Similarity Index is 12.0
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

Your Total Usage of the CSEARCH-Robot-Referee

682 Requests have been launched by molecules@robien.at
Year	Accept	Minor Revision	Major Revision	Reject	Only Prediction
2021	36	451	165	30

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Page has been automatically written by CSEARCH
CPU-Usage: Evaluation needed 8.405 seconds
Wolfgang.Robien(at)univie.ac.at

Carbon number	Chemical Shift Value	Multiplicity from Structure	Multiplicity from Experiment

1	162.80	S	-
2	97.90	D	-
3	167.40	D	-
4	93.10	S	-
5	157.70	S	-
6	154.10	S	-
7	139.90	D	-
8	120.40	S	-
9	109.30	D	-
10	145.40	S	-
11	108.10	S	-
12	184.60	S	-
13	102.80	S	-
14	55.90	Q	-
15	57.40	Q	-

Did you know ?

You can donate your private spectral data to the 'community'. Either when they have been published or aftera fixed period of time - you can select a 6, 12 or 18 month delay.

Reject; severe incompatibility detected

Compound: 1,8-DIHYDROXY-4,6-DIMETHOXYXANTHONE_COMPOUND-1 Project: MOLECULES,20,127[2015]CSEARCH-NUMBER:UWPA002007-20151028

Your Total Usage of the CSEARCH-Robot-Referee

You can donate your private spectral data to the 'community'.
Either when they have been published or after
a fixed period of time - you can select a 6, 12 or 18 month delay.

Compound: 1,8-DIHYDROXY-4,6-DIMETHOXYXANTHONE_COMPOUND-1

Project: MOLECULES,20,127[2015]CSEARCH-NUMBER:UWPA002007-20151028