NP-MRD: Showing NP-Card for dioncophylline a (NP0192876)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 10:11:17 UTC

Updated at

2022-09-04 10:11:17 UTC

NP-MRD ID

NP0192876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dioncophylline a

Description

Dioncophylline A belongs to the class of organic compounds known as naphthylisoquinolines. These are polycyclic aromatic compounds containing a naphthalene moiety linked to an isoquinoline through a CC or CN single bond. Dioncophylline A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. dioncophylline a is found in Ancistrocladus barteri, Ancistrocladus korupensis, Ancistrocladus letestui, Ancistrocladus tectorius, Apis cerana, Dioncophyllum thollonii, Habropetalum dawei and Triphyophyllum peltatum. dioncophylline a was first documented in 2013 (PMID: 23225585). Based on a literature review a small amount of articles have been published on dioncophylline A (PMID: 32629205) (PMID: 28121440) (PMID: 27438403) (PMID: 26272344).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042212112D          

 28 31  0  0  1  0            999 V2000
   -3.5724   -2.8875    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
   -2.8579   -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 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
   -2.1434   -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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -2.1434    2.0625    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    0.0000   -0.0000    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   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   -1.2375    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
  3 28  2  0  0  0  0
  7 28  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    6.5019    1.3252    1.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5229    0.5885    0.9985 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1616    0.7099    1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6284    1.5790    2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761    1.6991    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    0.9327    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161    0.0493    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -0.7074    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -0.6017    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142   -1.3685    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781   -1.1754    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -0.2600    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895    0.5152   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1295    0.3222   -0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    1.1052   -1.4156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949    1.5284   -1.2008 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3169    1.0958   -2.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    1.7431   -0.6765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1755    0.4755   -0.5162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6804    0.5710   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6423   -0.1303    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529   -1.5956   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561   -2.4059   -1.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227   -1.7212   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -0.9557   -0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -1.0786   -0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5162   -1.9937   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -0.0633    0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417    0.8319    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1521    2.3738    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4114    1.4916    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    2.2088    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770    2.3939    3.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360    0.9979    1.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548   -2.0847    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0179   -1.7684    2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218    1.7886   -1.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    2.5182   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3896    0.9773   -2.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8459    0.1054   -2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973    1.8466   -3.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    2.3560    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8750   -0.1837   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9901    1.2386    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0513   -0.4612   -0.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0374    0.8715   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1076   -1.0915    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7681    0.6367    1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -3.3362   -1.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -1.8490   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9653   -2.7919   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359   -2.4371   -1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526   -3.0025   -1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3059   -1.6648   -2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6057   -2.1481   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 22  1  0
 22 23  1  0
 22  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 21  1  0
 21 19  1  0
 19 20  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 13  1  0
 13 14  2  0
 14 15  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 28  2  0
 28 25  1  0
 14  9  1  0
 28  7  1  0
 13 12  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 24 52  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 10 35  1  0
 11 36  1  0
 21 47  1  0
 21 48  1  0
 19 43  1  6
 20 44  1  0
 20 45  1  0
 20 46  1  0
 18 42  1  0
 16 38  1  6
 17 39  1  0
 17 40  1  0
 17 41  1  0
 15 37  1  0
  6 34  1  0
  5 33  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309042212112D          

 28 31  0  0  1  0            999 V2000
   -3.5724   -2.8875    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
   -2.8579   -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 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
   -2.1434   -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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -2.1434    2.0625    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    0.0000   -0.0000    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   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   -1.2375    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
  3 28  2  0  0  0  0
  7 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C(C2=CC=C3C[C@@H](C)N[C@H](C)C3=C2O)C2=CC=CC(OC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1

> <INCHI_KEY>
MXIZZLBQRBAZEX-HUUCEWRRSA-N

> <FORMULA>
C24H27NO3

> <MOLECULAR_WEIGHT>
377.484

> <EXACT_MASS>
377.199093733

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.93293076240057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

> <JCHEM_LOGP>
3.8179229763249727

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.846939915203849

> <JCHEM_PKA_STRONGEST_BASIC>
10.300653437634699

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
112.98810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
dioncophylline A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -5.335   6.160   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12                                                       
CONECT   22    8   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₇NO₃

Average Mass

377.4840 Da

Monoisotopic Mass

377.19909 Da

IUPAC Name

(1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Traditional Name

dioncophylline A

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C(C2=CC=C3C[C@@H](C)N[C@H](C)C3=C2O)C2=CC=CC(OC)=C12

InChI Identifier

InChI=1S/C24H27NO3/c1-13-11-20(28-5)23-17(7-6-8-19(23)27-4)21(13)18-10-9-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1

InChI Key

MXIZZLBQRBAZEX-HUUCEWRRSA-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
Ancistrocladus barteri	LOTUS Database	35616633
Ancistrocladus korupensis	LOTUS Database	35616633
Ancistrocladus letestui	LOTUS Database	35616633
Ancistrocladus tectorius	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Dioncophyllum tholloni	LOTUS Database	35616633
Habropetalum dawei	LOTUS Database	35616633
Triphyophyllum peltatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthylisoquinolines. These are polycyclic aromatic compounds containing a naphthalene moiety linked to an isoquinoline through a CC or CN single bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Naphthylisoquinolines

Direct Parent

Naphthylisoquinolines

Alternative Parents

Substituents

Naphthylisoquinoline
Naphthalene
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:31504 )
isoquinolines (CHEBI:31504 )
methoxynaphthalene (CHEBI:31504 )
biaryl (CHEBI:31504 )
methylnaphthalenes (CHEBI:31504 )

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	3.82	ChemAxon
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.99 m³·mol⁻¹	ChemAxon
Polarizability	42.93 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

C00025302

Chemspider ID

391872

KEGG Compound ID

C12336

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443773

PDB ID

Not Available

ChEBI ID

31504

Good Scents ID

Not Available

References

General References

Bringmann G, Fayez S, Shamburger W, Feineis D, Winiarczyk S, Janecki R, Adaszek L: Naphthylisoquinoline alkaloids and their synthetic analogs as potent novel inhibitors against Babesia canis in vitro. Vet Parasitol. 2020 Jul;283:109177. doi: 10.1016/j.vetpar.2020.109177. Epub 2020 Jun 26. [PubMed:32629205 ]
Li J, Seupel R, Feineis D, Mudogo V, Kaiser M, Brun R, Brunnert D, Chatterjee M, Seo EJ, Efferth T, Bringmann G: Dioncophyllines C2, D2, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ileboensis with Potent Activities against Plasmodium falciparum and against Multiple Myeloma and Leukemia Cell Lines. J Nat Prod. 2017 Feb 24;80(2):443-458. doi: 10.1021/acs.jnatprod.6b00967. Epub 2017 Jan 25. [PubMed:28121440 ]
Bringmann G, Irmer A, Buttner T, Schaumloffel A, Zhang G, Seupel R, Feineis D, Fester K: Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African Liana Triphyophyllum peltatum. J Nat Prod. 2016 Aug 26;79(8):2094-103. doi: 10.1021/acs.jnatprod.6b00439. Epub 2016 Jul 20. [PubMed:27438403 ]
Hemberger Y, Zhang G, Brun R, Kaiser M, Bringmann G: Highly antiplasmodial non-natural oxidative products of dioncophylline A: synthesis, absolute configuration, and conformational stability. Chemistry. 2015 Oct 5;21(41):14507-18. doi: 10.1002/chem.201501657. Epub 2015 Aug 13. [PubMed:26272344 ]
Bringmann G, Zhang G, Buttner T, Bauckmann G, Kupfer T, Braunschweig H, Brun R, Mudogo V: Jozimine A2: the first dimeric Dioncophyllaceae-type naphthylisoquinoline alkaloid, with three chiral axes and high antiplasmodial activity. Chemistry. 2013 Jan 14;19(3):916-23. doi: 10.1002/chem.201202755. Epub 2012 Dec 5. [PubMed:23225585 ]
LOTUS database [Link]

Showing NP-Card for dioncophylline a (NP0192876)

MOL for NP0192876 (dioncophylline a)

3D MOL for NP0192876 (dioncophylline a)

3D SDF for NP0192876 (dioncophylline a)

3D-SDF for NP0192876 (dioncophylline a)

PDB for NP0192876 (dioncophylline a)

3D PDB for NP0192876 (dioncophylline a)

SMILES for NP0192876 (dioncophylline a)

INCHI for NP0192876 (dioncophylline a)

Structure for NP0192876 (dioncophylline a)

3D Structure for NP0192876 (dioncophylline a)