NP-MRD: Showing NP-Card for 1-methoxycanthinone (NP0219072)

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Record Information

Version

2.0

Created at

2022-09-05 19:56:50 UTC

Updated at

2022-09-05 19:56:50 UTC

NP-MRD ID

NP0219072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-methoxycanthinone

Description

1-Methoxycanthinone 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. 1-methoxycanthinone is found in Ailanthus altissima, Brucea antidysenterica, Hannoa chlorantha, Hannoa klaineana and Leitneria floridana. 1-methoxycanthinone was first documented in 1983 (PMID: 6619885). 1-Methoxycanthinone is a strong basic compound (based on its pKa) (PMID: 11141127) (PMID: 12590453).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506242D          

 19 22  0  0  0  0            999 V2000
    2.9220   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    1.3377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    3.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    3.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.7793    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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CN=C2C=CC(=O)N3C4=C(C=CC=C4)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O2/c1-19-12-8-16-10-6-7-13(18)17-11-5-3-2-4-9(11)14(12)15(10)17/h2-8H,1H3

> <INCHI_KEY>
LEPXKGXTXIACRO-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O2

> <MOLECULAR_WEIGHT>
250.257

> <EXACT_MASS>
250.07422757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.618311170198247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.6551983723333334

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.172305553114197

> <JCHEM_POLAR_SURFACE_AREA>
44.12

> <JCHEM_REFRACTIVITY>
70.95990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       5.454  -1.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.948  -0.752   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.472   0.712   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.966   1.032   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.490   2.497   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.520   3.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.459   5.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.705   6.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.112   5.758   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.357   6.663   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       5.273   4.226   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.518   3.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.025   3.641   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.055   2.497   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.579   1.032   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.073   0.712   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.043   1.857   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.503   1.857   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.027   3.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    3   19                                                  
CONECT   19   18    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
1-Methoxycanthin-6-one	ChEBI

Chemical Formula

C₁₅H₁₀N₂O₂

Average Mass

250.2570 Da

Monoisotopic Mass

250.07423 Da

IUPAC Name

8-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Traditional Name

8-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CN=C2C=CC(=O)N3C4=C(C=CC=C4)C1=C23

InChI Identifier

InChI=1S/C15H10N2O2/c1-19-12-8-16-10-6-7-13(18)17-11-5-3-2-4-9(11)14(12)15(10)17/h2-8H,1H3

InChI Key

LEPXKGXTXIACRO-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

Species Name	Source	Reference
Ailanthus altissima	LOTUS Database	35616633
Brucea antidysenterica	LOTUS Database	35616633
Hannoa chlorantha	LOTUS Database	35616633
Hannoa klaineana	LOTUS Database	35616633
Leitneria floridana	LOTUS Database	35616633

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
Diazanaphthalene
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Pyridinone
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Lactam
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66700 )
organic heterotetracyclic compound (CHEBI:66700 )
indole alkaloid (CHEBI:66700 )

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	2.56	ALOGPS
logP	1.66	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	3.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.96 m³·mol⁻¹	ChemAxon
Polarizability	25.62 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

483522

PDB ID

Not Available

ChEBI ID

66700

Good Scents ID

Not Available

References

General References

Xu Z, Chang FR, Wang HK, Kashiwada Y, McPhail AT, Bastow KF, Tachibana Y, Cosentino M, Lee KH: Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana. J Nat Prod. 2000 Dec;63(12):1712-5. doi: 10.1021/np000260u. [PubMed:11141127 ]
De Feo V, De Martino L, Quaranta E, Pizza C: Isolation of phytotoxic compounds from tree-of-heaven (Ailanthus altissima swingle). J Agric Food Chem. 2003 Feb 26;51(5):1177-80. doi: 10.1021/jf020686+. [PubMed:12590453 ]
Anderson LA, Harris A, Phillipson JD: Production of cytotoxic canthin-6-one alkaloids by Ailanthus altissima plant cell cultures. J Nat Prod. 1983 May-Jun;46(3):374-8. doi: 10.1021/np50027a014. [PubMed:6619885 ]
LOTUS database [Link]

Showing NP-Card for 1-methoxycanthinone (NP0219072)

MOL for NP0219072 (1-methoxycanthinone)

3D MOL for NP0219072 (1-methoxycanthinone)

3D SDF for NP0219072 (1-methoxycanthinone)

3D-SDF for NP0219072 (1-methoxycanthinone)

PDB for NP0219072 (1-methoxycanthinone)

3D PDB for NP0219072 (1-methoxycanthinone)

SMILES for NP0219072 (1-methoxycanthinone)

INCHI for NP0219072 (1-methoxycanthinone)

Structure for NP0219072 (1-methoxycanthinone)

3D Structure for NP0219072 (1-methoxycanthinone)