NP-MRD: Showing NP-Card for 4-carbomethoxy-5-keto-1,6-naphthyridine (NP0331608)

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Record Information

Version

2.0

Created at

2023-05-04 08:00:10 UTC

Updated at

2026-02-06 00:05:09 UTC

NP-MRD ID

NP0331608

Natural Product DOI

https://doi.org/10.57994/0589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-carbomethoxy-5-keto-1,6-naphthyridine

Description

4-Carbomethoxy-5-keto-1,6-naphthyridine belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom. 4-carbomethoxy-5-keto-1,6-naphthyridine was first documented in 2023 (PMID: 37088929). Based on a literature review very few articles have been published on 4-carbomethoxy-5-keto-1,6-naphthyridine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305042310002D          

 15 16  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 O   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000   -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
    1.4289   -0.0000    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
    2.1434   -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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=NC=CC2=C1C(=O)C=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C10H8N2O3/c1-15-10(14)9-8-6(2-4-12-9)11-5-3-7(8)13/h2-5H,1H3,(H,11,13)

> <INCHI_KEY>
HRKFFHDZLGWTTP-UHFFFAOYSA-N

> <FORMULA>
C10H8N2O3

> <MOLECULAR_WEIGHT>
204.185

> <EXACT_MASS>
204.053492126

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.209313149040817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-oxo-1,4-dihydro-1,6-naphthyridine-5-carboxylate

> <JCHEM_LOGP>
0.9215848150000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.15548152062601

> <JCHEM_PKA_STRONGEST_BASIC>
2.529522259445966

> <JCHEM_POLAR_SURFACE_AREA>
68.29

> <JCHEM_REFRACTIVITY>
54.515100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-oxo-1H-1,6-naphthyridine-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-23         0                                  
HETATM    1  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -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  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    9                                                            
CONECT   14    2   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₈N₂O₃

Average Mass

204.1850 Da

Monoisotopic Mass

204.05349 Da

IUPAC Name

methyl 4-oxo-1,4-dihydro-1,6-naphthyridine-5-carboxylate

Traditional Name

methyl 4-oxo-1H-1,6-naphthyridine-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=NC=CC2=C1C(=O)C=CN2

InChI Identifier

InChI=1S/C10H8N2O3/c1-15-10(14)9-8-6(2-4-12-9)11-5-3-7(8)13/h2-5H,1H3,(H,11,13)

InChI Key

HRKFFHDZLGWTTP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	gongkaikai1005@bzmc.edu.cn	Not Available	Not Available	2023-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	gongkaikai1005@bzmc.edu.cn	Not Available	Not Available	2023-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	gongkaikai1005@bzmc.edu.cn	Not Available	Not Available	2023-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	gongkaikai1005@bzmc.edu.cn	Not Available	Not Available	2023-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	gongkaikai1005@bzmc.edu.cn	Not Available	Not Available	2023-05-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aaptos suberitoides		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthyridines. These are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridines

Alternative Parents

Substituents

Naphthyridine
Pyridine carboxylic acid or derivatives
Pyridine carboxylic acid
Gamma-keto acid
2-halopyridine
Methylpyridine
Fatty acid ester
Dihydropyridine
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Pyridine
Keto acid
Heteroaromatic compound
Vinylogous amide
Alpha,beta-unsaturated ketone
Methyl ester
Secondary ketimine
Enone
Acryloyl-group
Ketone
Ketimine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
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	0.92	ChemAxon
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	2.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.52 m³·mol⁻¹	ChemAxon
Polarizability	19.21 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu M, Zhang Z, He Q, Qi S, Sun K, Miao S, Wu Y, Gong K: Anti-Inflammatory Effects of New Naphthyridine from Sponge Aaptos suberitoides in LPS-Stimulated RAW 264.7 Macrophages via Regulation of MAPK and Nrf2 Signaling Pathways. Chem Biodivers. 2023 Jun;20(6):e202300410. doi: 10.1002/cbdv.202300410. Epub 2023 May 12. [PubMed:37088929 ]
DOI: 10.1002/cbdv.202300410

Showing NP-Card for 4-carbomethoxy-5-keto-1,6-naphthyridine (NP0331608)

MOL for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

3D MOL for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

3D SDF for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

3D-SDF for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

PDB for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

3D PDB for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

SMILES for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

INCHI for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

Structure for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)

3D Structure for NP0331608 (4-carbomethoxy-5-keto-1,6-naphthyridine)