NP-MRD: Showing NP-Card for 5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one (NP0067930)

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Record Information

Version

2.0

Created at

2022-04-28 12:46:18 UTC

Updated at

2022-04-28 12:46:18 UTC

NP-MRD ID

NP0067930

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one

Description

Bianfugecine belongs to the class of organic compounds known as oxoisoaporphines. These are alkaloids with a structure that contains the isoaporphine skeleton with an oxo group at the 7-position. 5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one is found in Menispermum dauricum and Menispermum dauricum DC. . Bianfugecine is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
    6.0079    1.0533   -0.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    1.4452   -1.3185 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    0.8464   -0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7075   -0.1302    0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6115   -0.7308    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228   -0.3665    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    0.6115   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068    1.2200   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1601    0.9864   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607    1.8796   -1.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    0.3329   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    0.6302   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918    0.0227    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    0.3329   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3780    1.2870   -1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521   -0.9511    0.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -1.2794    1.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -2.2606    2.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434   -2.6016    2.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705   -1.9789    2.0186 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759   -1.0176    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1002   -0.6515    0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1549    1.4437    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0525   -0.0753   -0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7521    1.4365   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6975   -0.4500    0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930   -1.4999    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    1.9804   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7598    1.3948   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6432    1.2971   -2.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4149    2.2869   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4010    1.0668   -1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -1.4496    1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463   -2.7642    2.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   -3.3470    3.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 22  2  0
 22 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 17 16  2  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 12  2  0
  8  3  1  0
 12 11  1  0
 21  6  1  0
 21 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 18 34  1  0
 19 35  1  0
 16 33  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 12 29  1  0
M  END


  Mrv1533004231514312D          

 22 25  0  0  0  0            999 V2000
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    1.4289    0.8250    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
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
  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
  7  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)C(=O)C1=C3C(C=CN=C23)=CC(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO3/c1-21-11-3-4-13-14(8-11)18(20)15-9-12(22-2)7-10-5-6-19-17(13)16(10)15/h3-9H,1-2H3

> <INCHI_KEY>
OLIWOPDNTUVPQD-UHFFFAOYSA-N

> <FORMULA>
C18H13NO3

> <MOLECULAR_WEIGHT>
291.306

> <EXACT_MASS>
291.089543283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.928251460787354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
2.9488905233333327

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.4804485298203565

> <JCHEM_POLAR_SURFACE_AREA>
48.42

> <JCHEM_REFRACTIVITY>
82.5594

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,11-dimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   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                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21   11   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
5,9-Dimethoxy-7H-dibenzo(de,H)quinoline-7-one	MeSH

Chemical Formula

C₁₈H₁₃NO₃

Average Mass

291.3060 Da

Monoisotopic Mass

291.08954 Da

IUPAC Name

5,11-dimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

Traditional Name

5,11-dimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)C(=O)C1=C3C(C=CN=C23)=CC(OC)=C1

InChI Identifier

InChI=1S/C18H13NO3/c1-21-11-3-4-13-14(8-11)18(20)15-9-12(22-2)7-10-5-6-19-17(13)16(10)15/h3-9H,1-2H3

InChI Key

OLIWOPDNTUVPQD-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
Menispermum dauricum	LOTUS Database	35616633
Menispermum dauricum DC.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxoisoaporphines. These are alkaloids with a structure that contains the isoaporphine skeleton with an oxo group at the 7-position.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Isoaporphines

Sub Class

Oxoisoaporphines

Direct Parent

Oxoisoaporphines

Alternative Parents

Substituents

7-oxoisoaporphine
Anthracene
Isoquinoline
Anisole
Aryl ketone
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Ether
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen 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
logP	3.28	ALOGPS
logP	2.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	3.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	30.93 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

126021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one (NP0067930)

MOL for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

3D MOL for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

3D SDF for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

3D-SDF for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

PDB for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

3D PDB for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

SMILES for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

INCHI for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

Structure for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)

3D Structure for NP0067930 (5,9-Dimethoxy-7H-dibenzo[de,h]quinolin-7-one)