NP-MRD: Showing NP-Card for 2,3-Dihydromenisporphine (NP0067896)

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Record Information

Version

2.0

Created at

2022-04-28 12:44:18 UTC

Updated at

2022-04-28 12:44:18 UTC

NP-MRD ID

NP0067896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Dihydromenisporphine

Description

5,10,11-Trimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-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. 2,3-Dihydromenisporphine is found in Menispermum dauricum DC. . Based on a literature review very few articles have been published on 5,10,11-trimethoxy-16-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    6.3824   -0.8932   -1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0771   -1.3734   -1.4703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9768   -0.7063   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422    0.3615   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0777    1.0248    0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    0.5508    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.5225   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -1.1625   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -1.0203   -0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -2.0005   -1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -0.3542   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146   -0.8349   -0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -1.9132   -1.6018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2573   -3.2533   -1.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198   -0.2115   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871   -0.6765   -0.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6725   -0.1266   -0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0396    0.8606    0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7894    1.3619    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093    0.7374    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217    1.2163    0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    2.2041    1.5408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507    2.9342    2.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    2.5088    1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5298   -0.9546   -0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1115   -1.5820   -1.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5036    0.1536   -1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.6877    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1624    1.8619    1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -1.9986   -1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052   -3.5252   -0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -3.8793   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416   -3.5141   -0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4878   -0.9050   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0403    0.7473   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667    0.2028    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8899    1.3826    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.9265    3.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1719    4.0340    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    3.3871    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355    2.2638    2.8855 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  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 19 18  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 11 20  2  0
  4  3  1  0
 20 21  1  0
  9  7  1  0
 20 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  8 30  1  0
  5 29  1  0
  4 28  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 18 37  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END


  Mrv1652304282214442D          

 24 27  0  0  0  0            999 V2000
    3.5724   -1.2375    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    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
    2.8579   -2.4750    0.0000 N   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
    0.7145   -1.2375    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 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
    0.0000   -0.0000    0.0000 O   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
    4.2868    0.0000    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
    5.0013   -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
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 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
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 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
  1 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1=NCCC3=CC(OC)=C(OC)C(C2=O)=C13

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO4/c1-22-11-4-5-12-13(9-11)18(21)16-15-10(6-7-20-17(12)15)8-14(23-2)19(16)24-3/h4-5,8-9H,6-7H2,1-3H3

> <INCHI_KEY>
VBFVDZXMKBJFKN-UHFFFAOYSA-N

> <FORMULA>
C19H17NO4

> <MOLECULAR_WEIGHT>
323.348

> <EXACT_MASS>
323.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.52546882698803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,10,11-trimethoxy-16-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.7219183629999995

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.979588053315155

> <JCHEM_POLAR_SURFACE_AREA>
57.120000000000005

> <JCHEM_REFRACTIVITY>
90.80400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,10,11-trimethoxy-16-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    7   22                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21    1                                                       
CONECT   23   20   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇NO₄

Average Mass

323.3480 Da

Monoisotopic Mass

323.11576 Da

IUPAC Name

5,10,11-trimethoxy-16-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one

Traditional Name

5,10,11-trimethoxy-16-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=NCCC3=CC(OC)=C(OC)C(C2=O)=C13

InChI Identifier

InChI=1S/C19H17NO4/c1-22-11-4-5-12-13(9-11)18(21)16-15-10(6-7-20-17(12)15)8-14(23-2)19(16)24-3/h4-5,8-9H,6-7H2,1-3H3

InChI Key

VBFVDZXMKBJFKN-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
Dihydroisoquinoline
Anisole
Aryl ketone
Phenol ether
Alkyl aryl ether
Benzenoid
Ketimine
Ketone
Ether
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Imine
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
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	2.85	ALOGPS
logP	2.72	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	4.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.8 m³·mol⁻¹	ChemAxon
Polarizability	34.53 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

C00025733

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

85517875

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,3-Dihydromenisporphine (NP0067896)

MOL for NP0067896 (2,3-Dihydromenisporphine)

3D MOL for NP0067896 (2,3-Dihydromenisporphine)

3D SDF for NP0067896 (2,3-Dihydromenisporphine)

3D-SDF for NP0067896 (2,3-Dihydromenisporphine)

PDB for NP0067896 (2,3-Dihydromenisporphine)

3D PDB for NP0067896 (2,3-Dihydromenisporphine)

SMILES for NP0067896 (2,3-Dihydromenisporphine)

INCHI for NP0067896 (2,3-Dihydromenisporphine)

Structure for NP0067896 (2,3-Dihydromenisporphine)

3D Structure for NP0067896 (2,3-Dihydromenisporphine)