NP-MRD: Showing NP-Card for 6-Methoxymarcanine A (NP0086446)

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Record Information

Version

2.0

Created at

2022-04-29 06:44:52 UTC

Updated at

2022-04-29 06:44:52 UTC

NP-MRD ID

NP0086446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Methoxymarcanine A

Description

5-O-Methylmarcanine D belongs to the class of organic compounds known as benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. 6-Methoxymarcanine A is found in Annona glabra . 6-Methoxymarcanine A was first documented in 2010 (PMID: 20828184). Based on a literature review very few articles have been published on 5-O-Methylmarcanine D.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.1144    1.2598    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7496    0.9057    0.3352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    0.0462   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9551   -0.5553   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -1.4027   -2.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0269   -1.6877   -2.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -1.0752   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -0.2184   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    0.4272    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279    1.1974    1.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    0.1302    0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528    0.7106    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.6230    2.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    0.4331    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -0.4176    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3565   -0.6755    0.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -0.9697   -0.2476 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914   -0.7174   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -1.3330   -1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901   -2.1038   -2.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713    1.3307   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2816    2.2428    0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7104    0.5035    0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0156   -0.3508   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9554   -1.8746   -3.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5172   -2.3362   -3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814    1.1020    3.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9830    3.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1175    2.5505    2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125    0.8924    2.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -1.6204   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 18  2  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 18 19  1  0
 19 20  2  0
 19  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7  8  1  0
 12 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 17 31  1  0
 14 30  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
  6 26  1  0
  5 25  1  0
  4 24  1  0
M  END


  Mrv1652304292208442D          

 20 22  0  0  0  0            999 V2000
    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 O   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
    2.8579   -1.6500    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 C   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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   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
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 13  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  2  0  0  0  0
  4 17  1  0  0  0  0
 14 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
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C3=C(NC(=O)C=C3C)C(=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11NO4/c1-7-6-10(17)16-13-11(7)15(19)12-8(14(13)18)4-3-5-9(12)20-2/h3-6H,1-2H3,(H,16,17)

> <INCHI_KEY>
AMXHYKPAYOGDPO-UHFFFAOYSA-N

> <FORMULA>
C15H11NO4

> <MOLECULAR_WEIGHT>
269.256

> <EXACT_MASS>
269.068807838

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.63551742876649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-4-methyl-1H,2H,5H,10H-benzo[g]quinoline-2,5,10-trione

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
0.7004645589999998

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.420018742974856

> <JCHEM_PKA_STRONGEST_BASIC>
-4.538036906944666

> <JCHEM_POLAR_SURFACE_AREA>
72.47

> <JCHEM_REFRACTIVITY>
73.67120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methoxy-4-methyl-1H-benzo[g]quinoline-2,5,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.336  -5.390   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13    6   11   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14                                                            
CONECT   16    5                                                            
CONECT   17    4   14   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₁NO₄

Average Mass

269.2560 Da

Monoisotopic Mass

269.06881 Da

IUPAC Name

6-methoxy-4-methyl-1H,2H,5H,10H-benzo[g]quinoline-2,5,10-trione

Traditional Name

6-methoxy-4-methyl-1H-benzo[g]quinoline-2,5,10-trione

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(NC(=O)C=C3C)C(=O)C2=CC=C1

InChI Identifier

InChI=1S/C15H11NO4/c1-7-6-10(17)16-13-11(7)15(19)12-8(14(13)18)4-3-5-9(12)20-2/h3-6H,1-2H3,(H,16,17)

InChI Key

AMXHYKPAYOGDPO-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Annona glabra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Benzoquinolines

Alternative Parents

Substituents

Benzoquinoline
Quinoline quinone
Naphthalene
Anisole
Aryl ketone
Alkyl aryl ether
Methylpyridine
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Ketone
Lactam
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:70648 )
organonitrogen heterocyclic compound (CHEBI:70648 )

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	1.79	ALOGPS
logP	0.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.67 m³·mol⁻¹	ChemAxon
Polarizability	26.64 Å³	ChemAxon
Number of Rings	3	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

C00056719

Chemspider ID

26361557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49831442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tsai SF, Lee SS: Characterization of Acetylcholinesterase Inhibitory Constituents from Annona glabra Assisted by HPLC Microfractionation. J Nat Prod. 2010 Oct 22;73(10):1632-5. doi: 10.1021/np100247r. Epub 2010 Sep 9. [PubMed:20828184 ]

Showing NP-Card for 6-Methoxymarcanine A (NP0086446)

MOL for NP0086446 (6-Methoxymarcanine A)

3D MOL for NP0086446 (6-Methoxymarcanine A)

3D SDF for NP0086446 (6-Methoxymarcanine A)

3D-SDF for NP0086446 (6-Methoxymarcanine A)

PDB for NP0086446 (6-Methoxymarcanine A)

3D PDB for NP0086446 (6-Methoxymarcanine A)

SMILES for NP0086446 (6-Methoxymarcanine A)

INCHI for NP0086446 (6-Methoxymarcanine A)

Structure for NP0086446 (6-Methoxymarcanine A)

3D Structure for NP0086446 (6-Methoxymarcanine A)