NP-MRD: Showing NP-Card for Bianfugedine (NP0067931)

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Record Information

Version

2.0

Created at

2022-04-28 12:46:20 UTC

Updated at

2022-04-28 12:46:20 UTC

NP-MRD ID

NP0067931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bianfugedine

Description

16-Methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]Icosa-1(20),2(6),7,9,11,13(18),14,16-octaen-19-one 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. Bianfugedine is found in Menispermum dauricum DC. . 16-Methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]Icosa-1(20),2(6),7,9,11,13(18),14,16-octaen-19-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 38  0  0  0  0  0  0  0  0999 V2000
    5.0379   -1.9224    1.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -0.8951    0.3801 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -0.3609    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    0.6581   -0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.1995   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1474    0.7335   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -0.2857    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.8235    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -0.7600    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -1.6815    1.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3076   -0.1861    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -0.6468    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -0.0917    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7187    0.9260   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086    1.3734   -0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4927    2.3962   -1.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175    2.8589   -2.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1464    2.3142   -2.0093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512    1.3180   -1.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    0.8274   -0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876   -0.7464    1.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1213   -2.0004    1.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -1.6509    1.9039 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9294   -2.5219    0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142   -2.6322    1.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3056   -1.5591    2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920    1.0048   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    1.9848   -1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.6181    1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229    1.3891   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4521    2.8332   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643    3.6661   -3.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5474   -2.3536    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045   -2.7469    0.8445 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 20  2  0
 20 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 23  1  0
 23 22  1  0
 22 21  1  0
  8  3  1  0
 12 11  1  0
 19  6  1  0
 21 13  1  0
 19 20  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 16 31  1  0
 17 32  1  0
 14 30  1  0
 22 33  1  0
 22 34  1  0
M  END


  Mrv1533004161518402D          

 23 27  0  0  0  0            999 V2000
    0.9397    2.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454    2.8686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017    2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0521    1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6083    0.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141    1.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6637    1.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1074    2.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4694    2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190    2.7905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0257    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8314    1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2390    2.2891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0472    2.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1390    1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3877    0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1381    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2770   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208   -0.3549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9703    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761    0.6085    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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
 16 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
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)C(=O)C1=C3C(C=CN=C23)=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C18H11NO4/c1-21-10-2-3-11-12(7-10)17(20)15-14-9(4-5-19-16(11)14)6-13-18(15)23-8-22-13/h2-7H,8H2,1H3

> <INCHI_KEY>
BZLSBGPHEXHPAQ-UHFFFAOYSA-N

> <FORMULA>
C18H11NO4

> <MOLECULAR_WEIGHT>
305.289

> <EXACT_MASS>
305.068807838

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
31.21968034541506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]icosa-1(20),2(6),7,9,11,13,15,17-octaen-19-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.729795256666667

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.7262878459747735

> <JCHEM_POLAR_SURFACE_AREA>
57.650000000000006

> <JCHEM_REFRACTIVITY>
81.8631

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]icosa-1(20),2(6),7,9,11,13,15,17-octaen-19-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.754   5.024   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.258   5.355   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.296   4.217   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.831   2.750   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.869   1.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.373   1.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.839   3.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.801   4.548   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.343   3.741   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.809   5.209   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.381   2.604   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.885   2.934   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.646   4.273   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.155   3.963   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.326   2.433   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.924   1.797   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.458   0.329   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.954  -0.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.488  -1.469   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.984  -1.800   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.945  -0.663   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.411   0.805   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.915   1.136   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   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22   11   18                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
Bianfugedine	MeSH
5,6-Methylenedioxy-9-methoxy-7H-dibenzo(de,H)quinoline-7-one	MeSH

Chemical Formula

C₁₈H₁₁NO₄

Average Mass

305.2890 Da

Monoisotopic Mass

305.06881 Da

IUPAC Name

16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]icosa-1(20),2(6),7,9,11,13,15,17-octaen-19-one

Traditional Name

16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹³,¹⁸]icosa-1(20),2(6),7,9,11,13,15,17-octaen-19-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)C(=O)C1=C3C(C=CN=C23)=CC2=C1OCO2

InChI Identifier

InChI=1S/C18H11NO4/c1-21-10-2-3-11-12(7-10)17(20)15-14-9(4-5-19-16(11)14)6-13-18(15)23-8-22-13/h2-7H,8H2,1H3

InChI Key

BZLSBGPHEXHPAQ-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 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
Benzodioxole
Anisole
Aryl ketone
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Ketone
Azacycle
Oxacycle
Acetal
Ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	2.6	ALOGPS
logP	2.73	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	3.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.65 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.86 m³·mol⁻¹	ChemAxon
Polarizability	31.22 Å³	ChemAxon
Number of Rings	5	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

126022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bianfugedine (NP0067931)

MOL for NP0067931 (Bianfugedine)

3D MOL for NP0067931 (Bianfugedine)

3D SDF for NP0067931 (Bianfugedine)

3D-SDF for NP0067931 (Bianfugedine)

PDB for NP0067931 (Bianfugedine)

3D PDB for NP0067931 (Bianfugedine)

SMILES for NP0067931 (Bianfugedine)

INCHI for NP0067931 (Bianfugedine)

Structure for NP0067931 (Bianfugedine)

3D Structure for NP0067931 (Bianfugedine)