NP-MRD: Showing NP-Card for dioncophylline c (NP0253655)

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Record Information

Version

2.0

Created at

2022-09-07 17:35:34 UTC

Updated at

2022-09-07 17:35:34 UTC

NP-MRD ID

NP0253655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dioncophylline c

Description

Dioncophylline C 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 C 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 c is found in Ancistrocladus abbreviatus and Triphyophyllum peltatum. dioncophylline c was first documented in 1996 (PMID: 8762401). Based on a literature review a small amount of articles have been published on dioncophylline C (PMID: 17263326) (PMID: 17315144) (PMID: 22459968) (PMID: 9272557).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219352D          

 27 30  0  0  1  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -2.1434    1.2375    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
   -1.4289    2.4750    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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    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
    0.0000    0.8250    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   -0.4125    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
   -1.4289   -0.0000    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 13 19  1  0  0  0  0
 19 20  1  6  0  0  0
  7 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  3 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.6886    1.3247    1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.8934    0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756    0.4128    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566    0.3005    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.1800    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -0.2671    2.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.5717    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097   -1.0834    0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512   -2.4313    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8397   -2.9233    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -2.0779    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -2.5612    0.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -0.7378    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.2404    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1082    1.1987    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    2.0930    0.2542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7187    2.7764   -1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849    1.4269    0.9067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7949    0.2706    0.1139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1468   -0.2227    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7528   -0.4684   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -0.8618   -2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7562   -0.7916   -3.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448   -0.3118   -3.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.0982   -2.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9622    0.5541   -2.3647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0657    0.0217   -0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5684    1.9272    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0583    1.8599    2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0857    0.4215    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652    0.6172    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -0.9586    2.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989    0.7713    2.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6790   -0.6091    3.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -3.1061    0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -3.9762    0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3704   -3.5542    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672    1.3855   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    1.4422    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699    2.9237    0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3719    2.2289   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3180    3.8089   -1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8336    2.8770   -0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    2.0871    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8540    0.5929   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8115    0.6729    0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1845   -0.7036    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5802   -0.8446   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -1.2362   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449   -1.1086   -4.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5444   -0.2522   -4.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6953    0.9004   -1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 27  2  0
 27 25  1  0
 25 26  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  4  3  1  0
 14  8  1  0
 21 27  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 26 52  1  0
 24 51  1  0
 23 50  1  0
 22 49  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  4 31  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  1
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  1  0
 20 47  1  0
 20 48  1  0
M  END


  Mrv1652309072219352D          

 27 30  0  0  1  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -2.1434    1.2375    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
   -1.4289    2.4750    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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    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
    0.0000    0.8250    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   -0.4125    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
   -1.4289   -0.0000    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 13 19  1  0  0  0  0
 19 20  1  6  0  0  0
  7 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  3 27  2  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(O)=CC=CC2=C(C(C)=C1)C1=CC=C(O)C2=C1C[C@@H](C)N[C@@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C23H25NO3/c1-12-10-20(27-4)23-16(6-5-7-18(23)25)21(12)15-8-9-19(26)22-14(3)24-13(2)11-17(15)22/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1

> <INCHI_KEY>
NALOMJPIDNQZKW-ZIAGYGMSSA-N

> <FORMULA>
C23H25NO3

> <MOLECULAR_WEIGHT>
363.457

> <EXACT_MASS>
363.183443669

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.309364661119105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.550435580267384

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.246176818191719

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.157907511907613

> <JCHEM_PKA_STRONGEST_BASIC>
10.178210149226869

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
108.50580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
dioncophylline C

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   2.310   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  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -8.002   6.160   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
CONECT   21    7   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    3   21                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₅NO₃

Average Mass

363.4570 Da

Monoisotopic Mass

363.18344 Da

IUPAC Name

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

Traditional Name

dioncophylline C

CAS Registry Number

Not Available

SMILES

COC1=C2C(O)=CC=CC2=C(C(C)=C1)C1=CC=C(O)C2=C1C[C@@H](C)N[C@@H]2C

InChI Identifier

InChI=1S/C23H25NO3/c1-12-10-20(27-4)23-16(6-5-7-18(23)25)21(12)15-8-9-19(26)22-14(3)24-13(2)11-17(15)22/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1

InChI Key

NALOMJPIDNQZKW-ZIAGYGMSSA-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 abbreviatus	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
1-naphthol
Naphthalene
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:31505 )
naphthols (CHEBI:31505 )
isoquinoline alkaloid (CHEBI:31505 )
isoquinolines (CHEBI:31505 )
methoxynaphthalene (CHEBI:31505 )
biaryl (CHEBI:31505 )
methylnaphthalenes (CHEBI:31505 )

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	3.55	ChemAxon
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	10.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.51 m³·mol⁻¹	ChemAxon
Polarizability	40.31 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

C00025304

Chemspider ID

391873

KEGG Compound ID

C12337

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443774

PDB ID

Not Available

ChEBI ID

31505

Good Scents ID

Not Available

References

General References

Frosch T, Schmitt M, Noll T, Bringmann G, Schenzel K, Popp J: Ultrasensitive in situ tracing of the alkaloid dioncophylline A in the tropical liana Triphyophyllum peltatum by applying deep-UV resonance Raman microscopy. Anal Chem. 2007 Feb 1;79(3):986-93. doi: 10.1021/ac061526q. [PubMed:17263326 ]
Schwedhelm KF, Horstmann M, Faber JH, Reichert Y, Bringmann G, Faber C: The novel antimalarial compound dioncophylline C forms a complex with heme in solution. ChemMedChem. 2007 Apr;2(4):541-8. doi: 10.1002/cmdc.200600263. [PubMed:17315144 ]
Bringmann G, Zhang G, Olschlager T, Stich A, Wu J, Chatterjee M, Brun R: Highly selective antiplasmodial naphthylisoquinoline alkaloids from Ancistrocladus tectorius. Phytochemistry. 2013 Jul;91:220-8. doi: 10.1016/j.phytochem.2012.02.017. Epub 2012 Mar 27. [PubMed:22459968 ]
Francois G, Timperman G, Holenz J, Ake Assi L, Geuder T, Maes L, Dubois J, Hanocq M, Bringmann G: Naphthylisoquinoline alkaloids exhibit strong growth-inhibiting activities against Plasmodium falciparum and P. berghei in vitro--structure-activity relationships of dioncophylline C. Ann Trop Med Parasitol. 1996 Apr;90(2):115-23. doi: 10.1080/00034983.1996.11813035. [PubMed:8762401 ]
Francois G, Timperman G, Steenackers T, Assi LA, Holenz J, Bringmann G: In vitro inhibition of liver forms of the rodent malaria parasite Plasmodium berghei by naphthylisoquinoline alkaloids--structure-activity relationships of dioncophyllines A and C and ancistrocladine. Parasitol Res. 1997;83(7):673-9. doi: 10.1007/s004360050318. [PubMed:9272557 ]
LOTUS database [Link]

Showing NP-Card for dioncophylline c (NP0253655)

MOL for NP0253655 (dioncophylline c)

3D MOL for NP0253655 (dioncophylline c)

3D SDF for NP0253655 (dioncophylline c)

3D-SDF for NP0253655 (dioncophylline c)

PDB for NP0253655 (dioncophylline c)

3D PDB for NP0253655 (dioncophylline c)

SMILES for NP0253655 (dioncophylline c)

INCHI for NP0253655 (dioncophylline c)

Structure for NP0253655 (dioncophylline c)

3D Structure for NP0253655 (dioncophylline c)