CSEARCH Evaluation Report

Automatic Evaluation Report from CSEARCH
created on 2021-04-11 at 20:04:30
based on 340,554 reference spectra

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Request from: molecules@robien.at

Compound: MAHANIMBINE_COMPOUND-3

Project: MOLECULES,17,14449[2012]CSEARCH-NUMBER:UWIR000905-20140416

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: MAHANIMBINE_COMPOUND-3

Project: MOLECULES,17,14449[2012]CSEARCH-NUMBER:UWIR000905-20140416

Recommendation given here

Details of Prediction given here

Summary of Supplied Data

Understanding the Color Coding Scheme

Molecular formula is: C₂₃H₂₅NO Molecular weight is: 331.46 amu
INCHIKEY is: HTNVFUBCWIYPJN-QHCPKHFHBU

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

1 119.30 D -

2 128.90 D -

3 79.30 S -

4 150.90 S -

5 118.30 S -

6 121.80 D -

7 124.80 S -

8 117.90 S -

9 111.40 D -

10 124.90 D -

11 119.70 D -

12 119.90 D -

13 141.60 S -

14 136.90 S -

15 105.50 S -

16 16.20 Q -

17 26.40 Q -

18 42.10 T -

19 23.90 T -

20 125.50 D -

21 132.30 S -

22 17.60 Q -

23 25.80 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 )

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 C₂₃H₂₅NO

Search CHEMSPIDER for the molecular formula C₂₃H₂₅NO

(Description)

Performing Symmetry Analysis

Eventually Symmetry Error: Same environment - Different shiftvalue
Structural diagram

Basic Evaluation: Checking Multiplicities

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

From structure	23	9	8	2	4	11	12	0
From spectrum	23	9	8	2	4	11	12	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	115.8	117.3	116.5	119.3	2.8	Assigned by author Check assignment - maybe 118.30 ?	Only reference material with low similarity
2	127.6	125.1	126.3	128.9	2.6	Assigned by author Check assignment - maybe 125.50 ?	Only very few similar structures
3	77.7	80.3	79.7	79.3	0.4	Assigned by author
4	152.9	150.0	150.0	150.9	0.9	Assigned by author
5	118.0	122.6	122.6	118.3	4.3	Assigned by author Check assignment - maybe 121.80 ?	Inconsistent assignments in reference material
6	118.8	120.8	120.8	121.8	1.0	Assigned by author Check assignment - maybe 124.90 ?
7	117.1	117.0	117.0	124.8	7.8	Assigned by author Check assignment - maybe 117.90 ?
8	122.6	119.3	119.3	117.9	1.4	Assigned by author Check assignment - maybe 119.30 ?	Inconsistent assignments in reference material
9	120.9	119.9	119.9	111.4	8.5	Assigned by author Check assignment - maybe 119.90 ?
10	119.9	120.3	120.3	124.9	4.6	Assigned by author Check assignment - maybe 119.70 ?	Inconsistent assignments in reference material
11	128.0	127.6	127.6	119.7	7.9	Assigned by author Check assignment - maybe 128.90 ?	Inconsistent assignments in reference material
12	113.0	112.5	112.5	119.9	7.4	Assigned by author Check assignment - maybe 111.40 ?	Inconsistent assignments in reference material
13	140.2	136.1	136.1	141.6	5.5	Assigned by author Check assignment - maybe 136.90 ?	Inconsistent assignments in reference material
14	134.4	138.0	138.0	136.9	1.1	Assigned by author Check assignment - maybe 141.60 ?	Inconsistent assignments in reference material
15	108.2	104.2	104.2	105.5	1.3	Assigned by author	Only very few similar structures
16	16.5	16.5	16.5	16.2	0.3	Assigned by author
17	24.6	21.9	21.9	26.4	4.5	Assigned by author	Inconsistent assignments in reference material
18	38.2	40.9	40.9	42.1	1.2	Assigned by author
19	24.0	22.9	22.9	23.9	1.0	Assigned by author
20	124.4	123.8	123.8	125.5	1.7	Assigned by author Check assignment - maybe 124.80 ?
21	131.4	131.9	131.9	132.3	0.4	Assigned by author
22	18.0	17.8	17.8	17.6	0.2	Assigned by author
23	25.0	25.8	25.8	25.8	0.0	Assigned by author
Absolute Signed	3.03ppm (23) 0.60ppm (23)	2.95ppm (23) 0.80ppm (23)	2.90ppm (23) 0.81ppm (23)			1.18ppm (23) 0.81ppm (23)	Average deviation to experimental values ( Number of shift pairs used )
Structure representation by reference data over 4.7 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 2.9ppm

	Your assignment	Difference to predicted values

4 Entries found when searching CSEARCH for identical structures

(Description)

Identical structure: Entry # 1 of 4	J.NAT.PROD.,63,427(2000)
Solvent: CD3OD 23 carbons given 23 lines given 21 assigned lines 2 exchangeable shifts C₂₃H₂₅NO
HTNVFUBCWIYPJN Search Structure on WEB Availability of spectral data

Identical structure: Entry # 2 of 4	INT.J.PHYTOMED.,2,22(2010)
Solvent: CDCL3 23 carbons given 20 lines given 11 assigned lines 9 exchangeable shifts C₂₃H₂₅NO
HTNVFUBCWIYPJN Search Structure on WEB Availability of spectral data

Identical structure: Entry # 3 of 4	J.CHEM.PHARM.RES.,6,4,1093(2014)
Solvent: CDCL3 23 carbons given 23 lines given 23 assigned lines 0 exchangeable shifts C₂₃H₂₅NO
HTNVFUBCWIYPJN Search Structure on WEB Availability of spectral data

Identical structure: Entry # 4 of 4	MALAYS.J.ANAL.SCI.,11,173(2007)
Solvent: CDCL3 23 carbons given 22 lines given 22 assigned lines 0 exchangeable shifts C₂₃H₂₅NO
HTNVFUBCWIYPJN Search Structure on WEB Availability of spectral data

No alternative structure found when searching CSEARCH for identical spectra

(Description)

Overall Impression

Minor revision might be necessary - please check

Compound: MAHANIMBINE_COMPOUND-3

Project: MOLECULES,17,14449[2012]CSEARCH-NUMBER:UWIR000905-20140416

The CSEARCH Robot Referee recommends: Minor revision might be necessary - please check
Check integrity of page via electronic fingerprint

Assignment can be probably improved at 13 positions

5 Carbon positions ( out of 23 ) have a severe assignment problem

Spectrum prediction - minor inconsistencies found

4 Identical structures can be found in the CSEARCH-database

2 Carbon(s) might have a symmetry-problem

Experimental values

Predicted values

Matching map

Deviation per position ( Average is 2.9ppm )

Carbons having strong stereochemical effects

Contribution of methods

HOSE NET NET&HOSE NONE

Overall Similarity Index is 2.5
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

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 07:59:27	Minor	Evaluation	23	0	NO
This request	Minor	Evaluation	23	0

Your Total Usage of the CSEARCH-Robot-Referee

644 Requests have been launched by molecules@robien.at
Year	Accept	Minor Revision	Major Revision	Reject	Only Prediction
2021	35	433	155	21

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Page has been automatically written by CSEARCH
CPU-Usage: Evaluation needed 9.230 seconds
Wolfgang.Robien(at)univie.ac.at

Carbon number	Chemical Shift Value	Multiplicity from Structure	Multiplicity from Experiment

1	119.30	D	-
2	128.90	D	-
3	79.30	S	-
4	150.90	S	-
5	118.30	S	-
6	121.80	D	-
7	124.80	S	-
8	117.90	S	-
9	111.40	D	-
10	124.90	D	-
11	119.70	D	-
12	119.90	D	-
13	141.60	S	-
14	136.90	S	-
15	105.50	S	-
16	16.20	Q	-
17	26.40	Q	-
18	42.10	T	-
19	23.90	T	-
20	125.50	D	-
21	132.30	S	-
22	17.60	Q	-
23	25.80	Q	-

Did you know ?

You can link to the CSEARCH-Robot-Referee using the logo: Details how to do that are given here.

Minor revision might be necessary - please check

Compound: MAHANIMBINE_COMPOUND-3 Project: MOLECULES,17,14449[2012]CSEARCH-NUMBER:UWIR000905-20140416

Your Total Usage of the CSEARCH-Robot-Referee

You can link to the CSEARCH-Robot-Referee using the logo:
Details how to do that are given here.

Compound: MAHANIMBINE_COMPOUND-3

Project: MOLECULES,17,14449[2012]CSEARCH-NUMBER:UWIR000905-20140416