NP-MRD: Showing NP-Card for 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate (NP0237952)

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Record Information

Version

2.0

Created at

2022-09-06 21:14:41 UTC

Updated at

2022-09-06 21:14:41 UTC

NP-MRD ID

NP0237952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate

Description

Rhinacanthin D belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate is found in Rhinacanthus nasutus. 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate was first documented in 2009 (PMID: 19772749). Based on a literature review a small amount of articles have been published on Rhinacanthin D (PMID: 33860009) (PMID: 29491638) (PMID: 29200728) (PMID: 25869958).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223142D          

 30 33  0  0  0  0            999 V2000
   -0.3020   -1.1270    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
   -1.1270    0.3020    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
   -2.1434   -0.4125    0.0000 O   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
   -2.8579   -1.6500    0.0000 O   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
   -4.2868   -0.8250    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
   -4.4584    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    1.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144    0.9645    0.0000 O   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
    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   -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
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -0.4420   -0.4520    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    0.3726   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    1.7278   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -0.3613   -1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456   -0.3665   -0.8330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900   -0.9626   -1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477   -1.4928   -2.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4396   -1.0122   -0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -1.6149   -1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154   -1.6415   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7869   -1.0602    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6641   -0.4548    1.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106   -0.4378    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0161    0.0304    2.7322 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4449    0.0241    2.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8071   -0.9555    1.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5075    0.2267   -1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662    0.6479   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6260   -0.3356   -0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3174   -1.6652   -0.9548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979   -0.0140   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148   -1.0110    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0282   -0.7311    0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3725    0.5756    1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4769    1.5673    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2551    1.2942    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3586    2.3836   -0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589    3.6009   -0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0644    2.0429   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782    3.0000   -1.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4986   -0.4811    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1180    0.0209    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094   -1.4985    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    1.6296   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1984    2.2087    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    2.4022   -1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -1.4031   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    0.1498   -2.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5100   -2.0766   -2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5967   -2.1239   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6302    0.0519    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8772    1.0205    2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385   -0.2740    3.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284   -0.8358   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    0.7878   -2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826   -2.3435   -1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5345   -2.0404    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7334   -1.5343    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3302    0.7933    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7164    2.6213    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
  2 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 13  8  1  0
 29 18  1  0
 12 11  1  0
 26 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  9 39  1  0
 10 40  1  0
 15 42  1  0
 15 43  1  0
 13 41  1  0
 17 44  1  0
 17 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
M  END


  Mrv1652309062223142D          

 30 33  0  0  0  0            999 V2000
   -0.3020   -1.1270    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
   -1.1270    0.3020    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
   -2.1434   -0.4125    0.0000 O   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
   -2.8579   -1.6500    0.0000 O   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
   -4.2868   -0.8250    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
   -4.4584    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    1.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144    0.9645    0.0000 O   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
    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   -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
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0237952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(COC(=O)C1=CC=C2OCOC2=C1)CC1=C(O)C2=CC=CC=C2C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O7/c1-23(2,11-28-22(27)13-7-8-17-18(9-13)30-12-29-17)10-16-19(24)14-5-3-4-6-15(14)20(25)21(16)26/h3-9,24H,10-12H2,1-2H3

> <INCHI_KEY>
OBJIGRUMXMZJRX-UHFFFAOYSA-N

> <FORMULA>
C23H20O7

> <MOLECULAR_WEIGHT>
408.406

> <EXACT_MASS>
408.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.904723651334116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1-hydroxy-3,4-dioxo-3,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl 2H-1,3-benzodioxole-5-carboxylate

> <JCHEM_LOGP>
4.162268457000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.307425372055061

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7532791973089665

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
108.0037

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2H-1,3-benzodioxole-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.564  -2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.104   0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.322   3.046   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.854   3.207   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.480   1.800   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    2   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   18   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Rhinacanthin-D	MeSH

Chemical Formula

C₂₃H₂₀O₇

Average Mass

408.4060 Da

Monoisotopic Mass

408.12090 Da

IUPAC Name

3-(1-hydroxy-3,4-dioxo-3,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl 2H-1,3-benzodioxole-5-carboxylate

Traditional Name

3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2H-1,3-benzodioxole-5-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)(COC(=O)C1=CC=C2OCOC2=C1)CC1=C(O)C2=CC=CC=C2C(=O)C1=O

InChI Identifier

InChI=1S/C23H20O7/c1-23(2,11-28-22(27)13-7-8-17-18(9-13)30-12-29-17)10-16-19(24)14-5-3-4-6-15(14)20(25)21(16)26/h3-9,24H,10-12H2,1-2H3

InChI Key

OBJIGRUMXMZJRX-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, 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
Rhinacanthus nasutus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
1-naphthol
Benzodioxole
Quinone
Aryl ketone
Vinylogous acid
Cyclic ketone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	4.16	ChemAxon
pKa (Strongest Acidic)	5.31	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108 m³·mol⁻¹	ChemAxon
Polarizability	41.9 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00041096

Chemspider ID

409188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

465430

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dey D, Paul PK, Al Azad S, Al Mazid MF, Khan AM, Sharif MA, Rahman MH: Molecular optimization, docking, and dynamic simulation profiling of selective aromatic phytochemical ligands in blocking the SARS-CoV-2 S protein attachment to ACE2 receptor: an in silico approach of targeted drug designing. J Adv Vet Anim Res. 2021 Mar 5;8(1):24-35. doi: 10.5455/javar.2021.h481. eCollection 2021 Mar. [PubMed:33860009 ]
Shah MA, Jakkawanpitak C, Sermwittayawong D, Panichayupakaranant P: Rhinacanthins-rich Extract Enhances Glucose Uptake and Inhibits Adipogenesis in 3T3-L1 Adipocytes and L6 Myotubes. Pharmacogn Mag. 2018 Jan;13(Suppl 4):S817-S821. doi: 10.4103/pm.pm_236_17. Epub 2018 Jan 31. [PubMed:29491638 ]
Shah MA, Muhammad H, Mehmood Y, Khalil R, Ul-Haq Z, Panichayupakaranant P: Superoxide Scavenging and Antiglycation Activity of Rhinacanthins-rich Extract Obtained from the Leaves of Rhinacanthus nasutus. Pharmacogn Mag. 2017 Oct-Dec;13(52):652-658. doi: 10.4103/pm.pm_196_17. Epub 2017 Nov 13. [PubMed:29200728 ]
Kotewong R, Pouyfung P, Duangkaew P, Prasopthum A, Rongnoparut P: Synergy between rhinacanthins from Rhinacanthus nasutus in inhibition against mosquito cytochrome P450 enzymes. Parasitol Res. 2015 Jul;114(7):2567-79. doi: 10.1007/s00436-015-4461-8. Epub 2015 Apr 15. [PubMed:25869958 ]
Panichayupakaranant P, Charoonratana T, Sirikatitham A: RP-HPLC analysis of rhinacanthins in Rhinacanthus nasutus: validation and application for the preparation of rhinacanthin high-yielding extract. J Chromatogr Sci. 2009 Sep;47(8):705-8. doi: 10.1093/chromsci/47.8.705. [PubMed:19772749 ]
LOTUS database [Link]

Showing NP-Card for 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate (NP0237952)

MOL for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

3D MOL for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

3D SDF for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

3D-SDF for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

PDB for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

3D PDB for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

SMILES for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

INCHI for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

Structure for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)

3D Structure for NP0237952 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2h-1,3-benzodioxole-5-carboxylate)