NP-MRD: Showing NP-Card for (2-methyl-4-oxoquinolin-1-yl)methyl acetate (NP0154922)

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Record Information

Version

2.0

Created at

2022-09-02 11:54:24 UTC

Updated at

2022-09-02 11:54:24 UTC

NP-MRD ID

NP0154922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-methyl-4-oxoquinolin-1-yl)methyl acetate

Description

(2-Methyl-4-oxo-1,4-dihydroquinolin-1-yl)methyl acetate belongs to the class of organic compounds known as hydroquinolones. (2-methyl-4-oxoquinolin-1-yl)methyl acetate is found in Boronia lanceolata. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group (2-methyl-4-oxo-1,4-dihydroquinolin-1-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.3799   -0.3486    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -0.2731   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6907   -0.5182   -1.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0124    0.0498    0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222    0.0835   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    0.4306   -0.5539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6614    1.7065   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577    2.8000   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466    2.0390   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345    1.0503    0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198    1.3435    0.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3902   -0.2525    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861   -1.2330    0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -2.5562    0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6355   -2.8723    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455   -1.8765   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825   -0.5359   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9563    0.0220    1.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600   -1.3941    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    0.2604    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983   -0.7982   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247    0.9325   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3922    2.8614   -2.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    2.6667   -0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285    3.7783   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    3.0633   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2973   -1.0028    0.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5905   -3.3590    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -3.8980    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318   -2.1694   -0.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1533004171516542D          

 17 18  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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   -1.6500    0.0000 N   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
    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 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 16  1  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCN1C(C)=CC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO3/c1-9-7-13(16)11-5-3-4-6-12(11)14(9)8-17-10(2)15/h3-7H,8H2,1-2H3

> <INCHI_KEY>
NOOPPAOIYCLISV-UHFFFAOYSA-N

> <FORMULA>
C13H13NO3

> <MOLECULAR_WEIGHT>
231.251

> <EXACT_MASS>
231.089543283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.935484526590233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2-methyl-4-oxo-1,4-dihydroquinolin-1-yl)methyl acetate

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.8490594010000003

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.91624111867994

> <JCHEM_PKA_STRONGEST_BASIC>
-2.604358964487919

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
65.32590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-methyl-4-oxoquinolin-1-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   11                                                  
CONECT   17    7                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
(2-Methyl-4-oxo-1,4-dihydroquinolin-1-yl)methyl acetic acid	Generator
Acetate [2-methyl-4-oxoquinolin-1(4H)-yl]methyl ester	Generator

Chemical Formula

C₁₃H₁₃NO₃

Average Mass

231.2510 Da

Monoisotopic Mass

231.08954 Da

IUPAC Name

(2-methyl-4-oxo-1,4-dihydroquinolin-1-yl)methyl acetate

Traditional Name

(2-methyl-4-oxoquinolin-1-yl)methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCN1C(C)=CC(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C13H13NO3/c1-9-7-13(16)11-5-3-4-6-12(11)14(9)8-17-10(2)15/h3-7H,8H2,1-2H3

InChI Key

NOOPPAOIYCLISV-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
Boronia lanceolata	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
Methylpyridine
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
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	1.45	ALOGPS
logP	1.85	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	16.92	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.33 m³·mol⁻¹	ChemAxon
Polarizability	23.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

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

86170453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-methyl-4-oxoquinolin-1-yl)methyl acetate (NP0154922)

MOL for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

3D MOL for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

3D SDF for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

3D-SDF for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

PDB for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

3D PDB for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

SMILES for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

INCHI for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

Structure for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)

3D Structure for NP0154922 ((2-methyl-4-oxoquinolin-1-yl)methyl acetate)