NP-MRD: Showing NP-Card for Eduline (NP0086151)

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Record Information

Version

2.0

Created at

2022-04-29 06:30:47 UTC

Updated at

2022-04-29 06:30:47 UTC

NP-MRD ID

NP0086151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eduline

Description

Eduline, also known as O-butyrotoluidide, belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. Eduline is a moderately basic compound (based on its pKa). Outside of the human body, Eduline has been detected, but not quantified in, pomes. Eduline is found in Casimiroa edulis , Orixa japonica and Skimmia japonica. This could make eduline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.6978    1.1251    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1076   -0.1373    0.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7383   -0.2894    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188   -1.4900    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -1.6818    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9860   -0.6440    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5939    0.5555    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    0.7445    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    1.5805   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271    2.6890   -0.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    1.3564   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1383    0.1426   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -0.0624   -0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -0.5252   -1.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605   -0.7319   -1.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2441   -0.4670   -0.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7834   -0.0033    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4392    0.2066    0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -0.8410    0.1564 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9579   -2.1212    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7190    1.2046    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117    1.9636    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7102    1.3100   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -2.3239    1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639   -2.6105    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946    1.7064    0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2018    2.1556   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402   -0.7399   -2.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957   -1.0929   -2.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2920   -0.6197   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4781    0.2100    1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966    0.5701    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0577   -1.9971    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7049   -2.4425    1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -2.8980   -0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 19  1  0
 19 20  1  0
 19 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4  3  1  0
 18 13  1  0
  9  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  8 26  1  0
  5 25  1  0
  4 24  1  0
 20 33  1  0
 20 34  1  0
 20 35  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv0541 05061311582D          

 20 22  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)N(C)C(=CC2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO2/c1-18-15-9-8-13(20-2)10-14(15)17(19)11-16(18)12-6-4-3-5-7-12/h3-11H,1-2H3

> <INCHI_KEY>
GFUAPSNFZWUMBP-UHFFFAOYSA-N

> <FORMULA>
C17H15NO2

> <MOLECULAR_WEIGHT>
265.3065

> <EXACT_MASS>
265.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.298465765045023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-1-methyl-2-phenyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.9260956240000002

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.59310543384794

> <JCHEM_PKA_STRONGEST_BASIC>
2.6583857036405747

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
81.3998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methoxy-1-methyl-2-phenylquinolin-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8    9   13                                                       
CONECT    9    8   15                                                       
CONECT   10   13   14                                                       
CONECT   11   16   17                                                       
CONECT   12    6    7   16                                                  
CONECT   13    8   10   20                                                  
CONECT   14   10   15   17                                                  
CONECT   15    9   14   18                                                  
CONECT   16   11   12   18                                                  
CONECT   17   11   14   19                                                  
CONECT   18    1   15   16                                                  
CONECT   19   17                                                            
CONECT   20    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
6-Methoxy-1-methyl-2-phenyl-4(1H)-quinolinone, 9ci	HMDB
O-Butyrotoluidide	HMDB
O-Butyrotoluidine	HMDB
Eduline	MeSH

Chemical Formula

C₁₇H₁₅NO₂

Average Mass

265.3065 Da

Monoisotopic Mass

265.11028 Da

IUPAC Name

6-methoxy-1-methyl-2-phenyl-1,4-dihydroquinolin-4-one

Traditional Name

6-methoxy-1-methyl-2-phenylquinolin-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)N(C)C(=CC2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H15NO2/c1-18-15-9-8-13(20-2)10-14(15)17(19)11-16(18)12-6-4-3-5-7-12/h3-11H,1-2H3

InChI Key

GFUAPSNFZWUMBP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Casimiroa edulis	Plant	KNApSAcK
Orixa japonica	LOTUS Database	35616633
Skimmia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Phenylquinolines

Alternative Parents

Substituents

Phenylquinoline
2-phenylpyridine
Dihydroquinolone
Dihydroquinoline
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Azacycle
Ether
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.26	ALOGPS
logP	2.93	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	16.59	ChemAxon
pKa (Strongest Basic)	2.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.4 m³·mol⁻¹	ChemAxon
Polarizability	29.3 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040597

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020383

KNApSAcK ID

Not Available

Chemspider ID

540603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

622180

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Eduline (NP0086151)

MOL for NP0086151 (Eduline)

3D MOL for NP0086151 (Eduline)

3D SDF for NP0086151 (Eduline)

3D-SDF for NP0086151 (Eduline)

PDB for NP0086151 (Eduline)

3D PDB for NP0086151 (Eduline)

SMILES for NP0086151 (Eduline)

INCHI for NP0086151 (Eduline)

Structure for NP0086151 (Eduline)

3D Structure for NP0086151 (Eduline)