NP-MRD: Showing NP-Card for ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate (NP0226657)

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Record Information

Version

2.0

Created at

2022-09-06 05:46:21 UTC

Updated at

2022-09-06 05:46:22 UTC

NP-MRD ID

NP0226657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate

Description

Ethyl 6-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Ethyl 6-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241518292D          

 18 19  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    2.1434   -2.8875    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 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
    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
  4  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
  8 10  1  0  0  0  0
 10 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  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 18  1  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1=CC(=O)NC2=CC=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO4/c1-3-18-13(16)10-7-12(15)14-11-5-4-8(17-2)6-9(10)11/h4-7H,3H2,1-2H3,(H,14,15)

> <INCHI_KEY>
PNBJBGMPLMTKFP-UHFFFAOYSA-N

> <FORMULA>
C13H13NO4

> <MOLECULAR_WEIGHT>
247.25

> <EXACT_MASS>
247.084457903

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.082650740766816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 6-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.6665936240000003

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.70864639571754

> <JCHEM_PKA_STRONGEST_BASIC>
-2.52385880816421

> <JCHEM_POLAR_SURFACE_AREA>
64.63000000000001

> <JCHEM_REFRACTIVITY>
67.25930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 6-methoxy-2-oxo-1H-quinoline-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  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                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 6-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid	Generator

Chemical Formula

C₁₃H₁₃NO₄

Average Mass

247.2500 Da

Monoisotopic Mass

247.08446 Da

IUPAC Name

ethyl 6-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

Traditional Name

ethyl 6-methoxy-2-oxo-1H-quinoline-4-carboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=CC(=O)NC2=CC=C(OC)C=C12

InChI Identifier

InChI=1S/C13H13NO4/c1-3-18-13(16)10-7-12(15)14-11-5-4-8(17-2)6-9(10)11/h4-7H,3H2,1-2H3,(H,14,15)

InChI Key

PNBJBGMPLMTKFP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Anisole
Pyridinone
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Ether
Azacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen 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	2.01	ALOGPS
logP	1.67	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.26 m³·mol⁻¹	ChemAxon
Polarizability	25.08 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

287262

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate (NP0226657)

MOL for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

3D MOL for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

3D SDF for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

3D-SDF for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

PDB for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

3D PDB for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

SMILES for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

INCHI for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

Structure for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)

3D Structure for NP0226657 (ethyl 2-hydroxy-6-methoxyquinoline-4-carboxylate)