NP-MRD: Showing NP-Card for 4,9-Dimethoxycanthin-6-one (NP0138352)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-05-31 17:56:07 UTC

Updated at

2022-05-31 17:56:07 UTC

NP-MRD ID

NP0138352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9-Dimethoxycanthin-6-one

Description

4,9-Dimethoxycanthin-6-one belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. It was first documented in 2010 (PMID: 20184012). Based on a literature review very few articles have been published on 4,9-Dimethoxycanthin-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    4.9904    1.5287   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7522    0.1718   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980   -0.4023   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.7458    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703   -2.3330    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757   -1.5272    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -1.7983    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1591   -2.9355    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -2.7846    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1352   -1.5860    0.0912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.4710   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099    0.7907   -0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2684    0.9511   -0.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9395    2.1640   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9885    1.8073   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    1.6173   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    2.5553   -0.5390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305    0.3578   -0.1980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957   -0.1498   -0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.3887   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0412   -0.6102   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3416    2.2032    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0454    1.7338   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    1.7180   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -2.3752    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359   -3.3954    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492   -3.8623    0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -3.6595    0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530    3.0564   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8354    2.1528    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3275    2.1792   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    2.8046   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    1.4553   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20 19  1  0
 19  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 21  2  0
 21 18  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
  4  3  1  0
 21  7  1  0
 18 19  1  0
 12 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 33  1  0
  5 26  1  0
  4 25  1  0
  8 27  1  0
  9 28  1  0
 15 32  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv1652305312219562D          

 21 24  0  0  0  0            999 V2000
    4.7764    1.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244    1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174    1.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654    2.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584    2.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035    1.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    0.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625    1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9785    1.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4265    0.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.8035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0834    2.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236    2.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    2.7300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3048    3.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9722    4.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    3.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    3.7633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419    3.3025    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  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
  6  9  1  0  0  0  0
  9 10  2  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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1=CC=NC3=C1N2C(=O)C=C3OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O3/c1-20-9-3-4-10-11-5-6-17-15-13(21-2)8-14(19)18(16(11)15)12(10)7-9/h3-8H,1-2H3

> <INCHI_KEY>
WBMNWMYQWQQWHM-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O3

> <MOLECULAR_WEIGHT>
280.283

> <EXACT_MASS>
280.084792254

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.10009262681966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,13-dimethoxy-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),6,8,10(15),11,13-heptaen-2-one

> <JCHEM_LOGP>
1.1666680803333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.3045449154943456

> <JCHEM_POLAR_SURFACE_AREA>
53.35000000000001

> <JCHEM_REFRACTIVITY>
77.67849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,13-dimethoxy-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-3,5(16),6,8,10(15),11,13-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  C   UNK     0       8.916   2.542   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.886   3.687   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.379   3.367   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.349   4.511   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.842   4.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.367   2.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.397   1.582   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.903   1.902   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.827   2.726   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.796   1.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.710   1.902   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.186   3.367   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.156   4.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.351   4.191   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.597   5.096   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.436   6.628   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.681   7.533   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.029   7.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.217   6.349   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.601   7.025   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.878   6.165   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂N₂O₃

Average Mass

280.2830 Da

Monoisotopic Mass

280.08479 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1270001-72-3

SMILES

COC1=CC2=C(C=C1)C1=CC=NC3=C1N2C(=O)C=C3OC

InChI Identifier

InChI=1S/C16H12N2O3/c1-20-9-3-4-10-11-5-6-17-15-13(21-2)8-14(19)18(16(11)15)12(10)7-9/h3-8H,1-2H3

InChI Key

WBMNWMYQWQQWHM-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Anisole
Phenol ether
Alkyl aryl ether
Pyridinone
Pyridine
Benzenoid
Vinylogous ester
Heteroaromatic compound
Pyrrole
Lactam
Organoheterocyclic compound
Azacycle
Ether
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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

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

28287202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004796

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyake K, Tezuka Y, Awale S, Li F, Kadota S: Canthin-6-one alkaloids and a tirucallanoid from Eurycoma longifolia and their cytotoxic activity against a human HT-1080 fibrosarcoma cell line. Nat Prod Commun. 2010 Jan;5(1):17-22. [PubMed:20184012 ]

Showing NP-Card for 4,9-Dimethoxycanthin-6-one (NP0138352)

MOL for NP0138352 (4,9-Dimethoxycanthin-6-one)

3D MOL for NP0138352 (4,9-Dimethoxycanthin-6-one)

3D SDF for NP0138352 (4,9-Dimethoxycanthin-6-one)

3D-SDF for NP0138352 (4,9-Dimethoxycanthin-6-one)

PDB for NP0138352 (4,9-Dimethoxycanthin-6-one)

3D PDB for NP0138352 (4,9-Dimethoxycanthin-6-one)

SMILES for NP0138352 (4,9-Dimethoxycanthin-6-one)

INCHI for NP0138352 (4,9-Dimethoxycanthin-6-one)

Structure for NP0138352 (4,9-Dimethoxycanthin-6-one)

3D Structure for NP0138352 (4,9-Dimethoxycanthin-6-one)