NP-MRD: Showing NP-Card for N-Methylschinifoline (NP0083581)

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Record Information

Version

2.0

Created at

2022-04-29 04:34:46 UTC

Updated at

2022-04-29 04:34:46 UTC

NP-MRD ID

NP0083581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Methylschinifoline

Description

N-Methylschinifoline belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. N-Methylschinifoline is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-Methylschinifoline has been detected, but not quantified in, fruits and herbs and spices. N-Methylschinifoline is found in Glycosmis citrifolia, Severinia buxifolia , Zanthoxylum schinifolium and Zanthoxylum simulans. This could make N-methylschinifoline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    4.8533    1.6186    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    0.6480    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363   -0.7416    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5505    1.0253    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741    0.0695    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2437    0.2159    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -0.9255   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871   -2.1303   -0.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115   -2.6690   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857   -0.8105   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028   -1.9299   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0672   -1.7609   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -0.5431   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380    0.5509   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4560    0.4210    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    1.5363    0.1974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3576    2.8314    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762    1.4165    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286    2.4954    0.4333 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666    2.6518    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.4111    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -1.4381    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198   -0.7888    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.0547   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    2.0353    0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036   -0.9570    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -3.0587   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5361   -1.8952   -2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1907   -3.4826   -1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190   -2.9003   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -2.6223   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7246   -0.3670   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2463    1.5404    0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    3.6010    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0392    3.0754   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8547    2.9317    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  6 18  1  0
 18 19  2  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  7  1  0
 10 15  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  5 26  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  1 20  1  0
  1 21  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 14 33  1  0
 13 32  1  0
 12 31  1  0
 11 30  1  0
M  END


  Mrv0541 05061311472D          

 19 20  0  0  0  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    1.4289    0.0000    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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 19  4  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(\C=C\C(C)=C)C(=O)N(C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO2/c1-11(2)9-10-13-15(19-4)12-7-5-6-8-14(12)17(3)16(13)18/h5-10H,1H2,2-4H3/b10-9+

> <INCHI_KEY>
KUJRJLUCKWRGPV-MDZDMXLPSA-N

> <FORMULA>
C16H17NO2

> <MOLECULAR_WEIGHT>
255.3117

> <EXACT_MASS>
255.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.545021261063027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-1-methyl-3-[(1E)-3-methylbuta-1,3-dien-1-yl]-1,2-dihydroquinolin-2-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.1271970136666667

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6418235577692369

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
78.6414

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-1-methyl-3-[(1E)-3-methylbuta-1,3-dien-1-yl]quinolin-2-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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   17                                                            
CONECT    4   19                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   12                                                       
CONECT    8    6   14                                                       
CONECT    9   10   11                                                       
CONECT   10    9   13                                                       
CONECT   11    1    2    9                                                  
CONECT   12    7   14   15                                                  
CONECT   13   10   15   16                                                  
CONECT   14    8   12   17                                                  
CONECT   15   12   13   19                                                  
CONECT   16   13   17   18                                                  
CONECT   17    3   14   16                                                  
CONECT   18   16                                                            
CONECT   19    4   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₂

Average Mass

255.3117 Da

Monoisotopic Mass

255.12593 Da

IUPAC Name

4-methoxy-1-methyl-3-[(1E)-3-methylbuta-1,3-dien-1-yl]-1,2-dihydroquinolin-2-one

Traditional Name

4-methoxy-1-methyl-3-[(1E)-3-methylbuta-1,3-dien-1-yl]quinolin-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(C)=C)C(=O)N(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C16H17NO2/c1-11(2)9-10-13-15(19-4)12-7-5-6-8-14(12)17(3)16(13)18/h5-10H,1H2,2-4H3/b10-9+

InChI Key

KUJRJLUCKWRGPV-MDZDMXLPSA-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
Glycosmis citrifolia	Plant	KNApSAcK
Severinia buxifolia	Plant	KNApSAcK
Zanthoxylum schinifolium	Plant	KNApSAcK
Zanthoxylum simulans	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Alkyl aryl ether
Pyridinone
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous ester
Lactam
Azacycle
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen 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	2.86	ALOGPS
logP	2.13	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.64 m³·mol⁻¹	ChemAxon
Polarizability	28.55 Å³	ChemAxon
Number of Rings	2	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

HMDB0040381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020113

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101652163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-Methylschinifoline (NP0083581)

MOL for NP0083581 (N-Methylschinifoline)

3D MOL for NP0083581 (N-Methylschinifoline)

3D SDF for NP0083581 (N-Methylschinifoline)

3D-SDF for NP0083581 (N-Methylschinifoline)

PDB for NP0083581 (N-Methylschinifoline)

3D PDB for NP0083581 (N-Methylschinifoline)

SMILES for NP0083581 (N-Methylschinifoline)

INCHI for NP0083581 (N-Methylschinifoline)

Structure for NP0083581 (N-Methylschinifoline)

3D Structure for NP0083581 (N-Methylschinifoline)