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Showing NP-Card for 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate (NP0252655)

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Record Information
Version2.0
Created at2022-09-07 16:14:17 UTC
Updated at2022-09-07 16:14:17 UTC
NP-MRD IDNP0252655
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate
DescriptionRhinacanthin K 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 (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate is found in Rhinacanthus nasutus. Based on a literature review very few articles have been published on Rhinacanthin K.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)


  Mrv1652309072218142D          

 32 33  0  0  0  0            999 V2000
   -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
   -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
   -4.2868    1.6500    0.0000 C   0  0  0  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
   -5.4138    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    2.7770    0.0000 O   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
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    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
   -2.1434   -0.4125    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1270    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
    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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
Download

3D MOL for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)

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3D SDF for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)

  Mrv1652309072218142D          

 32 33  0  0  0  0            999 V2000
   -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
   -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
   -4.2868    1.6500    0.0000 C   0  0  0  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
   -5.4138    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    2.7770    0.0000 O   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
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    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
   -2.1434   -0.4125    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1270    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
    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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0252655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(C)(O)CC\C=C(/C)C(=O)OCC(C)(C)CC1=C(O)C2=CC=CC=C2C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-15(9-8-12-25(5,31)16(2)26)23(30)32-14-24(3,4)13-19-20(27)17-10-6-7-11-18(17)21(28)22(19)29/h6-7,9-11,16,26-27,31H,8,12-14H2,1-5H3/b15-9+

> <INCHI_KEY>
XVWTTYRIYXHBGO-OQLLNIDSSA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.59154757914897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1-hydroxy-3,4-dioxo-3,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl (2E)-6,7-dihydroxy-2,6-dimethyloct-2-enoate

> <JCHEM_LOGP>
3.775947839666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.85306668783306

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.618442917768441

> <JCHEM_PKA_STRONGEST_BASIC>
-3.120252313151129

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
122.39479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2E)-6,7-dihydroxy-2,6-dimethyloct-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)
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PDB for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)
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      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.106   2.516   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -8.566   5.184   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -12.003   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.564  -2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.104   0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   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
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   20   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

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3D PDB for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)
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SMILES for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)
CC(O)C(C)(O)CC\C=C(/C)C(=O)OCC(C)(C)CC1=C(O)C2=CC=CC=C2C(=O)C1=O
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INCHI for NP0252655 (3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2e)-6,7-dihydroxy-2,6-dimethyloct-2-enoate)
InChI=1S/C25H32O7/c1-15(9-8-12-25(5,31)16(2)26)23(30)32-14-24(3,4)13-19-20(27)17-10-6-7-11-18(17)21(28)22(19)29/h6-7,9-11,16,26-27,31H,8,12-14H2,1-5H3/b15-9+
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SynonymsNot Available
Chemical FormulaC25H32O7
Average Mass444.5240 Da
Monoisotopic Mass444.21480 Da
IUPAC Name3-(1-hydroxy-3,4-dioxo-3,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl (2E)-6,7-dihydroxy-2,6-dimethyloct-2-enoate
Traditional Name3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl (2E)-6,7-dihydroxy-2,6-dimethyloct-2-enoate
CAS Registry NumberNot Available
SMILES
CC(O)C(C)(O)CC\C=C(/C)C(=O)OCC(C)(C)CC1=C(O)C2=CC=CC=C2C(=O)C1=O
InChI Identifier
InChI=1S/C25H32O7/c1-15(9-8-12-25(5,31)16(2)26)23(30)32-14-24(3,4)13-19-20(27)17-10-6-7-11-18(17)21(28)22(19)29/h6-7,9-11,16,26-27,31H,8,12-14H2,1-5H3/b15-9+
InChI KeyXVWTTYRIYXHBGO-OQLLNIDSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Rhinacanthus nasutusLOTUS Database
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).
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassNaphthalenes  
Sub ClassNaphthoquinones  
Direct ParentNaphthoquinones  
Alternative Parents
Substituents
  • Naphthoquinone
    • 

  • 1-naphthol
    • 

  • Aromatic monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Monoterpenoid
    • 

  • Fatty alcohol
    • 

  • Aryl ketone
    • 

  • Quinone
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tertiary alcohol
    • 

  • Ketone
    • 

  • 1,2-diol
    • 

  • Carboxylic acid ester
    • 

  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Enol
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.78ChemAxon
pKa (Strongest Acidic)5.62ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity122.39 m³·mol⁻¹ChemAxon
Polarizability48.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00041101  
Chemspider ID8941032  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10765714  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]