NP-MRD: Showing NP-Card for Eugeniinaline C (NP0332329)

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Record Information

Version

2.0

Created at

2024-01-04 12:00:53 UTC

Updated at

2025-02-11 15:44:17 UTC

NP-MRD ID

NP0332329

Natural Product DOI

https://doi.org/10.57994/1531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eugeniinaline C

Description

Eugeniinaline C 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 Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings.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. Eugeniinaline C was first documented in 2024 (PMID: 38284153). Based on a literature review very few articles have been published on Eugeniinaline C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042412002D          

 25 28  0  0  1  0            999 V2000
    1.2792   -2.4820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209   -1.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -2.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.8827    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.8107   -1.7101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -0.3072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7695   -1.1224    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.1272   -1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695   -0.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1272   -0.0099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8968    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0240    1.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545    0.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    1.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    0.2105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574    1.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    1.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549   -0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -1.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3423   -1.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -1.0368    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
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  CHG  2   4  -1   8   1
M  END


  Mrv2104 01042412002D          

 25 28  0  0  1  0            999 V2000
    1.2792   -2.4820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209   -1.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -2.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.8827    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.8107   -1.7101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -0.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -0.3072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7695   -1.1224    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.1272   -1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6423   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695   -0.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1272   -0.0099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8968    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0240    1.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545    0.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878    1.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    0.2105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574    1.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    1.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729   -0.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549   -0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -1.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3423   -1.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -1.0368    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
  3  5  2  0  0  0  0
  2  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
NP0332329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C([O-])=O)=C1/C2=CC=CC=C2N2C(=O)CC[C@@]3(CC)CCC[NH2+][C@@]123

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O3/c1-2-18-9-5-11-20-19(18)14(12-17(23)24)13-6-3-4-7-15(13)21(19)16(22)8-10-18/h3-4,6-7,12,20H,2,5,8-11H2,1H3,(H,23,24)/b14-12-/t18-,19+/m1/s1

> <INCHI_KEY>
DUYLTUMBBYQQKI-KKUFWVNYSA-N

> <FORMULA>
C19H22N2O3

> <MOLECULAR_WEIGHT>
326.396

> <EXACT_MASS>
326.163042576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.55360889484297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,13Z,13aR)-13-(carboxylatomethylidene)-4a-ethyl-7-oxo-1H,2H,3H,4H,4aH,5H,6H,7H,13H-indolo[1,2-j]1,8-naphthyridin-1-ium

> <JCHEM_LOGP>
0.33607974815165004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7368166451022096

> <JCHEM_PKA_STRONGEST_BASIC>
7.6370088985286415

> <JCHEM_POLAR_SURFACE_AREA>
77.05

> <JCHEM_REFRACTIVITY>
112.4922

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,13Z,13aR)-13-(carboxylatomethylidene)-4a-ethyl-7-oxo-1H,2H,3H,4H,5H,6H-indolo[1,2-j]1,8-naphthyridin-1-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  H   UNK     0       2.388  -4.633   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.346  -3.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.143  -3.894   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.545  -5.381   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      -1.513  -3.192   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.004  -1.661   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.199  -0.574   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.436  -2.095   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       0.238  -3.062   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.199  -2.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.436  -0.985   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.238  -0.018   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.674   0.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.912   2.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.475   1.503   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.724   2.470   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.398   0.393   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.160   1.915   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.359   2.881   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.688  -0.449   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.176  -0.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.263  -1.145   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.861  -2.631   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.372  -3.027   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.286  -1.935   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   25                                                  
CONECT    7    6    8   12   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   15                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   18                                                       
CONECT   17    7   18   20                                                  
CONECT   18   17   16   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20    6                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O₃

Average Mass

326.3960 Da

Monoisotopic Mass

326.16304 Da

IUPAC Name

(4aR,13Z,13aR)-13-(carboxylatomethylidene)-4a-ethyl-7-oxo-1H,2H,3H,4H,4aH,5H,6H,7H,13H-indolo[1,2-j]1,8-naphthyridin-1-ium

Traditional Name

(4aR,13Z,13aR)-13-(carboxylatomethylidene)-4a-ethyl-7-oxo-1H,2H,3H,4H,5H,6H-indolo[1,2-j]1,8-naphthyridin-1-ium

CAS Registry Number

Not Available

SMILES

[H]\C(C([O-])=O)=C1/C2=CC=CC=C2N2C(=O)CC[C@@]3(CC)CCC[NH2+][C@@]123

InChI Identifier

InChI=1S/C19H22N2O3/c1-2-18-9-5-11-20-19(18)14(12-17(23)24)13-6-3-4-7-15(13)21(19)16(22)8-10-18/h3-4,6-7,12,20H,2,5,8-11H2,1H3,(H,23,24)/b14-12-/t18-,19+/m1/s1

InChI Key

DUYLTUMBBYQQKI-KKUFWVNYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.13300065, CD₃OD, simulated)	yylow@um.edu.my	Department of Chemistry, Faculty of Science, Universiti Malaya	Yun-Yee Low	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Leuconotis eugeniifolia		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
Azaspirodecane
Indolizidine
Indole or derivatives
N-acylpyrrolidine
Piperidinone
Heterocyclic fatty acid
Delta-lactam
Branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Piperidine
N-acyl-amine
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Lactam
Carboxylic acid salt
Carboxamide group
Amino acid or derivatives
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
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	0.34	ChemAxon
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	7.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.49 m³·mol⁻¹	ChemAxon
Polarizability	34.55 Å³	ChemAxon
Number of Rings	4	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

DOI: 10.1021/acs.jnatprod.3c00960

Showing NP-Card for Eugeniinaline C (NP0332329)

MOL for NP0332329 (Eugeniinaline C)

3D MOL for NP0332329 (Eugeniinaline C)

3D SDF for NP0332329 (Eugeniinaline C)

3D-SDF for NP0332329 (Eugeniinaline C)

PDB for NP0332329 (Eugeniinaline C)

3D PDB for NP0332329 (Eugeniinaline C)

SMILES for NP0332329 (Eugeniinaline C)

INCHI for NP0332329 (Eugeniinaline C)

Structure for NP0332329 (Eugeniinaline C)

3D Structure for NP0332329 (Eugeniinaline C)