NP-MRD: Showing NP-Card for 2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline (NP0239603)

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Record Information

Version

2.0

Created at

2022-09-06 23:14:10 UTC

Updated at

2022-09-06 23:14:11 UTC

NP-MRD ID

NP0239603

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline

Description

2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-1,4-dihydroquinoline belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. 2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline is found in Ruta chalepensis and Ruta graveolens. Based on a literature review very few articles have been published on 2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-1,4-dihydroquinoline.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.8304    3.0427    1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4655    2.2202    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.0361    0.6766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4383    0.9870    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -0.0166   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.1294   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3504   -0.5461   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7419   -0.4236   -1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525    0.3720   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7380    1.0538    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.9375    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    1.7720    0.9930 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9143    1.0610    0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140    0.6918   -0.5362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5712   -1.1605   -0.6152 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.3458   -1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817   -1.2184   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -2.3030   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1308   -2.3486   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7569   -1.2896    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -0.1928    0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -0.1659    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    3.9730    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182    2.5815    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805    3.3005    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    1.1202    1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608    1.8793    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924   -1.1477   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841   -0.9606   -2.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710    1.4646    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8069    1.6475    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8114    0.1483    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008   -2.4016   -2.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684   -2.4980   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5015   -3.2778   -0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -3.1680   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6939   -3.2260   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8129   -1.3560    0.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079    0.6285    1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 22  3  1  0
 11  6  1  0
 22 17  1  0
 10  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  1
  4 27  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
  7 28  1  0
  8 29  1  0
 13 31  1  0
 13 32  1  0
 11 30  1  0
M  END


  Mrv1652309072201142D          

 22 25  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    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
   -0.7145   -0.4125    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
   -1.4289    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   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
    2.1434   -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
    3.5724   -0.4125    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
    2.8579   -1.6500    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239603

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C=C(N(C)C2=CC=CC=C12)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO3/c1-19-14-6-4-3-5-13(14)17(20-2)10-15(19)12-7-8-16-18(9-12)22-11-21-16/h3-10,17H,11H2,1-2H3

> <INCHI_KEY>
JJXRDJDKEQLZBC-UHFFFAOYSA-N

> <FORMULA>
C18H17NO3

> <MOLECULAR_WEIGHT>
295.338

> <EXACT_MASS>
295.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.88752886872246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-1,4-dihydroquinoline

> <JCHEM_LOGP>
3.2091867946666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.06893348029356239

> <JCHEM_POLAR_SURFACE_AREA>
30.93

> <JCHEM_REFRACTIVITY>
86.05300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4H-quinoline

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.654   3.816   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.185   3.977   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.812   2.570   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17    3                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇NO₃

Average Mass

295.3380 Da

Monoisotopic Mass

295.12084 Da

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-1,4-dihydroquinoline

Traditional Name

2-(2H-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4H-quinoline

CAS Registry Number

Not Available

SMILES

COC1C=C(N(C)C2=CC=CC=C12)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C18H17NO3/c1-19-14-6-4-3-5-13(14)17(20-2)10-15(19)12-7-8-16-18(9-12)22-11-21-16/h3-10,17H,11H2,1-2H3

InChI Key

JJXRDJDKEQLZBC-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ruta chalepensis	LOTUS Database	35616633
Ruta graveolens	LOTUS Database	35616633

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
Benzodioxole
Tertiary aliphatic/aromatic amine
Benzenoid
Tertiary amine
Acetal
Dialkyl ether
Enamine
Ether
Oxacycle
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
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	3.21	ChemAxon
pKa (Strongest Basic)	-0.069	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.05 m³·mol⁻¹	ChemAxon
Polarizability	31.89 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4476572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317841

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline (NP0239603)

MOL for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

3D MOL for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

3D SDF for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

3D-SDF for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

PDB for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

3D PDB for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

SMILES for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

INCHI for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

Structure for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)

3D Structure for NP0239603 (2-(2h-1,3-benzodioxol-5-yl)-4-methoxy-1-methyl-4h-quinoline)