NP-MRD: Showing NP-Card for Melicopicine (NP0051243)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:52 UTC

Updated at

2022-04-27 22:37:52 UTC

NP-MRD ID

NP0051243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melicopicine

Description

Melicopicine belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Melicopicine is found in Acronychia baueri, Bauerella simplicifolia ssp.neo-scotica, Melicope fareana, Melicope leptococca, Sarcomelicope argirophylla, Sarcomelicope argyrophylla, Sarcomelicope follicularis, Sarcomelicope galuca, Sarcomelicope leiocarpa, Sarcomelicope megistophylla, Sarcomelicope simplicifolia, Teclea boiviniana, Teclea trichocarpa, Vepris sclerophylla, Vepris trichocarpa and Zanthoxylum simullans. Melicopicine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.1648   -1.1348    1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -1.0121   -0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -0.5672   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566    0.7777   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219    1.6425   -0.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6255    2.0746   -1.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540    1.2918   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5141    2.6528   -0.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    3.4532    0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4202    0.4531   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1654   -0.9253    0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239   -1.4089    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -2.7625    0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871   -3.6306   -0.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1760   -1.8158    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0123   -3.0710    0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4743   -1.3518    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179   -2.2540    0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8152   -1.8199    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414   -0.4771    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    0.4381    0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982    0.0199    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877    0.9223   -0.0472 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    2.3066   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0733   -1.7663    1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5256   -0.1268    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -1.5180    2.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    1.3572   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0611    3.0782   -1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    2.1992   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.9043    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5648    3.8554    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1360    4.3096    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197   -3.4007   -1.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -3.6714   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412   -4.6595   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -3.3311    0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246   -2.5497    0.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0443   -0.0927    0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226    1.4914    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184    2.4404   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3646    2.8320   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1888    2.8472    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 10  1  0
 10  7  2  0
  7  8  1  0
  8  9  1  0
  7  4  1  0
 10 11  1  0
 22 17  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
M  END


  Mrv1533004161520382D          

 24 26  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   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 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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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   -1.6500    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
    3.5724   -0.4125    0.0000 O   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   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
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=O)C3=CC=CC=C3N(C)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO5/c1-19-11-9-7-6-8-10(11)14(20)12-13(19)16(22-3)18(24-5)17(23-4)15(12)21-2/h6-9H,1-5H3

> <INCHI_KEY>
URPVDDXMEZAEJY-UHFFFAOYSA-N

> <FORMULA>
C18H19NO5

> <MOLECULAR_WEIGHT>
329.352

> <EXACT_MASS>
329.126322716

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.48227382360181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3,4-tetramethoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.4922698156666665

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.552334969896473

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
89.81119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melicopicine

> <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       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₅

Average Mass

329.3520 Da

Monoisotopic Mass

329.12632 Da

IUPAC Name

1,2,3,4-tetramethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

melicopicine

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C(=O)C3=CC=CC=C3N(C)C2=C1OC

InChI Identifier

InChI=1S/C18H19NO5/c1-19-11-9-7-6-8-10(11)14(20)12-13(19)16(22-3)18(24-5)17(23-4)15(12)21-2/h6-9H,1-5H3

InChI Key

URPVDDXMEZAEJY-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
Acronychia baueri	Plant	KNApSAcK
Bauerella simplicifolia ssp.neo-scotica	Plant	KNApSAcK
Melicope fareana	Plant	KNApSAcK
Melicope leptococca	Plant	KNApSAcK
Sarcomelicope argirophylla	Plant	KNApSAcK
Sarcomelicope argyrophylla	LOTUS Database	35616633
Sarcomelicope follicularis	Plant	KNApSAcK
Sarcomelicope galuca	Plant	KNApSAcK
Sarcomelicope leiocarpa	Plant	KNApSAcK
Sarcomelicope megistophylla	Plant	KNApSAcK
Sarcomelicope simplicifolia	LOTUS Database	35616633
Teclea boiviniana	Plant	KNApSAcK
Teclea trichocarpa	Plant	KNApSAcK
Vepris sclerophylla	Plant	KNApSAcK
Vepris trichocarpa	LOTUS Database	35616633
Zanthoxylum simullans	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
Dihydroquinoline
Anisole
Alkyl aryl ether
Pyridine
Benzenoid
Vinylogous ester
Vinylogous amide
Heteroaromatic compound
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acridines (CHEBI:6734 )
Acridone alkaloids (C10722 )

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	2.58	ALOGPS
logP	2.49	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.81 m³·mol⁻¹	ChemAxon
Polarizability	34.48 Å³	ChemAxon
Number of Rings	3	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

C00002186

Chemspider ID

Not Available

KEGG Compound ID

C10722

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Melicopicine (NP0051243)

MOL for NP0051243 (Melicopicine)

3D MOL for NP0051243 (Melicopicine)

3D SDF for NP0051243 (Melicopicine)

3D-SDF for NP0051243 (Melicopicine)

PDB for NP0051243 (Melicopicine)

3D PDB for NP0051243 (Melicopicine)

SMILES for NP0051243 (Melicopicine)

INCHI for NP0051243 (Melicopicine)

Structure for NP0051243 (Melicopicine)

3D Structure for NP0051243 (Melicopicine)