Automatic Evaluation Report from CSEARCH
created on 2021-04-27 at 10:16:30
based on 340,554 reference spectra



Did you know ?

When entering signal multiplicities use only couplings to directly bound hydrogens.
Couplings to 19F, 31P or other nuclei have to be ignored when using multiplicity information,




Request from: molecules@robien.at

Compound: APIGENIN_COMPOUND-4

Project: MOLECULES,19,13147[2014]CSEARCH-NUMBER:UWIR015107-20150808


Database Number of Entries Owner of Database


Please cite the CSEARCH-Robot-Referee as:

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


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 74,997 (A) CSEARCH-Data / Wolfgang Robien
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 56,549 (B) CSEARCH-Data / Wolfgang Robien
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 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
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 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: APIGENIN_COMPOUND-4

Project: MOLECULES,19,13147[2014]CSEARCH-NUMBER:UWIR015107-20150808

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: C15H10O5     Molecular weight is: 270.24 amu

INCHIKEY is: KZNIFHPLKGYRTM-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

1 164.10 S -
2 103.10 D -
3 181.60 S -
4 157.70 S -
5 162.00 S -
6 99.80 D -
7 164.00 S -
8 94.30 D -
9 104.10 S -
10 121.10 S -
11 128.20 D -
12 116.40 D -
13 161.50 S -
14 116.40 D -
15 128.20 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 138,184,003 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 C15H10O5


Search CHEMSPIDER for the molecular formula C15H10O5



(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

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
1 162.2 163.9 163.9 164.1 0.2 Assigned by author
Check assignment - maybe 164.00 ?
2 101.5 103.7 103.7 103.1 0.6 Assigned by author Inconsistent assignments in reference material
3 183.2 182.0 182.0 181.6 0.4 Assigned by author
4 104.4 104.4 104.4 157.7 53.3 Assigned by author
Check assignment - maybe 104.10 ?		 Inconsistent assignments in reference material
5 160.6 161.2 161.2 162.0 0.8 Assigned by author
6 99.2 99.1 99.1 99.8 0.7 Assigned by author
7 164.6 164.3 164.3 164.0 0.3 Assigned by author
Check assignment - maybe 164.10 ?
8 94.7 94.5 94.5 94.3 0.2 Assigned by author
9 158.8 158.5 158.5 104.1 54.4 Assigned by author
Check assignment - maybe 157.70 ?		 Inconsistent assignments in reference material
10 122.4 121.7 121.7 121.1 0.6 Assigned by author
11 128.8 128.6 128.6 128.2 0.4 Assigned by author
12 115.9 116.2 116.2 116.4 0.2 Assigned by author
13 161.9 161.3 161.3 161.5 0.2 Assigned by author
14 115.9 116.2 116.2 116.4 0.2 Assigned by author
15 128.8 128.6 128.6 128.2 0.4 Assigned by author
  Absolute  
Signed
   8.00ppm   (15)  
   -0.03ppm   (15)  
   7.53ppm   (15)  
   -0.11ppm   (15)  
   7.53ppm   (15)  
   -0.11ppm   (15)  

   0.40ppm   (15)  
   -0.11ppm   (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

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 7.5ppm

Quality bar



Spectrum
Spectrum
Spectrum


  Your assignment  
 Difference to predicted values 
Highlighting
Highlighting







25 Entries found when searching CSEARCH for identical structures

(Description)




Identical structure:
Entry # 1 of 25

HETEROCYCLES,16,2181(1981)

Solvent: UNKNOWN

15 carbons given
14 lines given
14 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 2 of 25

TETRAH.LETT.,17,1799(1976)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 3 of 25

PHYTOCHEM.,49,1147(1998)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 4 of 25

FITOTERAPIA,71,649(2000)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 5 of 25

PHYTOCHEM.,39,115(1995)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 6 of 25

TURK.J.CHEM.,26,581(2002)

Solvent: CD3OD

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 7 of 25

J.CHIN.CHEM.SOC.,51,1425(2004)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 8 of 25

PHYTOCHEM.,34,843(1993)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 9 of 25

PHYTOCHEM.,36,507(1994)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 10 of 25

PHYTOCHEM.,31,2483(1992)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 11 of 25

DER.PHARM.LETT.,6,54(2014)

Solvent: CD3OD

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 12 of 25

INT.J.NAT.PR.R.,3,74(2013)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 13 of 25

J.CHEM.PHARM.RES.,5,261(2013)

Solvent: C5D5N

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 14 of 25

J.CHIN.PHARM.SCI.,20,518(2011)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 15 of 25

J.CHIN.PHARM.SCI.,9,134(2000)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 16 of 25

J.CHIN.PHARM.SCI.,6,70(1997)

Solvent: UNKNOWN

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 17 of 25

J.CHIN.PHARM.SCI.,6,225(1997)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 18 of 25

AGR.BIOL.CHEM.,49,909(1985)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 19 of 25

AFR.J.MICBIOL.RES.,5,1001(2011)

Solvent: UNKNOWN

15 carbons given
15 lines given
11 assigned lines
4 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 20 of 25

AUST.J.B.APPL.SCI.,5,606(2011)

Solvent: CD3OD

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 21 of 25

INT.J.CH.BIOCH.SCI.,6,56(2014)

Solvent: DMSO-D6

15 carbons given
15 lines given
13 assigned lines
2 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 22 of 25

FOOD.CHEM.,164,150(2014)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 23 of 25

J.CHEM.PHARM.RES.,6,5,990(2014)

Solvent: DMSO-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 24 of 25

REC.NAT.PROD.,4,91(2010)

Solvent: DMSO-D6

15 carbons given
14 lines given
14 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure


Identical structure:
Entry # 25 of 25

PHARMACOG.J.,6,36(2014)

Solvent: ACETONE-D6

15 carbons given
15 lines given
15 assigned lines
0 exchangeable shifts

C15H10O5
Spectrum

KZNIFHPLKGYRTM

Search Structure on WEB

Availability of spectral data
Structure







No alternative structure found when searching CSEARCH for identical spectra

(Description)










Overall Impression


Reject
Quality bar



Reject; severe incompatibility detected




Compound: APIGENIN_COMPOUND-4

Project: MOLECULES,19,13147[2014]CSEARCH-NUMBER:UWIR015107-20150808


Reject


The CSEARCH Robot Referee recommends: Reject; severe incompatibility detected

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Experimental values
Highlighting
Predicted values
Highlighting
Matching map
Highlighting
Deviation per position ( Average is 7.5ppm )
Highlighting
Carbons having strong stereochemical effects
Highlighting
Contribution of methods
HOSE NET NET&HOSE NONE
Highlighting
Overall Similarity Index is 5.5
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 138,184,003 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 C15H10O5


Search CHEMSPIDER for the molecular formula C15H10O5



(Description)





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)
2021-02-26
02:41:30		 Minor Evaluation 15 0 NO Spectrum
2021-04-11
01:08:30		 Minor Evaluation 15 0 NO Spectrum
This request Reject Evaluation 15 0 Spectrum


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   680 Requests have been launched by molecules@robien.at   


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