NP-MRD: Showing NP-Card for 10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate (NP0282084)

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Record Information

Version

2.0

Created at

2022-09-09 08:47:06 UTC

Updated at

2022-09-09 08:47:07 UTC

NP-MRD ID

NP0282084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate

Description

Secalonic acid F, also known as secalonate F, belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. 10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate is found in Diploicia canescens. 10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate was first documented in 2004 (PMID: 15139208). Based on a literature review a significant number of articles have been published on Secalonic acid F (PMID: 35684504) (PMID: 29248948) (PMID: 31980363) (PMID: 35543239) (PMID: 32679716) (PMID: 23023390).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210472D          

 46 51  0  0  1  0            999 V2000
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092210472D          

 46 51  0  0  1  0            999 V2000
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0526  -10.2412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0874   -5.5201    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
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 14 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
  7 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
  5 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0282084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12OC3=CC=C(C(O)=C3C(O)=C1C(=O)C[C@H](C)[C@@H]2O)C1=CC=C2O[C@]3([C@H](O)[C@@H](C)CC(=O)C3=C(O)C2=C1O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,35-40H,9-10H2,1-4H3/t11-,12-,27-,28+,31+,32+/m0/s1

> <INCHI_KEY>
NFZJAYYORNVZNI-XIBZLVKHSA-N

> <FORMULA>
C32H30O14

> <MOLECULAR_WEIGHT>
638.578

> <EXACT_MASS>
638.163555646

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
62.44836543401559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10a,10'a-dimethyl (5R,5'S,6S,6'S,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5H,5'H,6H,6'H,7H,7'H,8H,8'H,10aH,10'aH-[2,2'-bixanthene]-10a,10'a-dicarboxylate

> <JCHEM_LOGP>
1.1894138046666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.503499329592937

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.83432611833345

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4941477970010704

> <JCHEM_POLAR_SURFACE_AREA>
226.57999999999993

> <JCHEM_REFRACTIVITY>
156.50020000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
10a,10'a-dimethyl (5R,5'S,6S,6'S,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5H,5'H,6H,6'H,7H,7'H-[2,2'-bixanthene]-10a,10'a-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.339 -18.480   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.005 -17.710   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.632 -19.117   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      18.672 -18.480   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.672 -20.020   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.763 -10.304   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39   45                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   36                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29   33                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28   14                                                       
CONECT   34   10   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    7   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    5   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43    5   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
Secalonate F	Generator

Chemical Formula

C₃₂H₃₀O₁₄

Average Mass

638.5780 Da

Monoisotopic Mass

638.16356 Da

IUPAC Name

10a,10'a-dimethyl (5R,5'S,6S,6'S,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5H,5'H,6H,6'H,7H,7'H,8H,8'H,10aH,10'aH-[2,2'-bixanthene]-10a,10'a-dicarboxylate

Traditional Name

10a,10'a-dimethyl (5R,5'S,6S,6'S,10aR,10'aR)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5H,5'H,6H,6'H,7H,7'H-[2,2'-bixanthene]-10a,10'a-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12OC3=CC=C(C(O)=C3C(O)=C1C(=O)C[C@H](C)[C@@H]2O)C1=CC=C2O[C@]3([C@H](O)[C@@H](C)CC(=O)C3=C(O)C2=C1O)C(=O)OC

InChI Identifier

InChI=1S/C32H30O14/c1-11-9-15(33)21-25(37)19-17(45-31(21,27(11)39)29(41)43-3)7-5-13(23(19)35)14-6-8-18-20(24(14)36)26(38)22-16(34)10-12(2)28(40)32(22,46-18)30(42)44-4/h5-8,11-12,27-28,35-40H,9-10H2,1-4H3/t11-,12-,27-,28+,31+,32+/m0/s1

InChI Key

NFZJAYYORNVZNI-XIBZLVKHSA-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
Diploicia canescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Benzenoid
Hydroxy acid
Cyclic alcohol
Vinylogous acid
Methyl ester
Carboxylic acid ester
Secondary alcohol
Ketone
Ether
Enol
Oxacycle
Carboxylic acid derivative
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen 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	1.19	ChemAxon
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	226.58 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	156.5 m³·mol⁻¹	ChemAxon
Polarizability	62.45 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00048116

Chemspider ID

161668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aengenvoort J, Sekeres M, Proksch P, Fritz G: Targeting Mechanisms of the DNA Damage Response (DDR) and DNA Repair by Natural Compounds to Improve cAT-Triggered Tumor Cell Death. Molecules. 2022 Jun 1;27(11). pii: molecules27113567. doi: 10.3390/molecules27113567. [PubMed:35684504 ]
Yodsing N, Lekphrom R, Sangsopha W, Aimi T, Boonlue S: Secondary Metabolites and Their Biological Activity from Aspergillus aculeatus KKU-CT2. Curr Microbiol. 2018 May;75(5):513-518. doi: 10.1007/s00284-017-1411-y. Epub 2017 Dec 16. [PubMed:29248948 ]
van Stuijvenberg J, Proksch P, Fritz G: Targeting the DNA damage response (DDR) by natural compounds. Bioorg Med Chem. 2020 Feb 15;28(4):115279. doi: 10.1016/j.bmc.2019.115279. Epub 2020 Jan 8. [PubMed:31980363 ]
Dinakar S, Gurubarath M, Dhananjayan K: Prediction of binding affinity of 1,2-diphenyline ketone analogues at adenosine triphosphate binding site of glycogen synthase kinase-3beta: a molecular docking and dynamic simulation study. J Biomol Struct Dyn. 2023 Jul;41(11):4847-4862. doi: 10.1080/07391102.2022.2074143. Epub 2022 May 11. [PubMed:35543239 ]
Ozenver N, Dawood M, Fleischer E, Klinger A, Efferth T: Chemometric and Transcriptomic Profiling, Microtubule Disruption and Cell Death Induction by Secalonic Acid in Tumor Cells. Molecules. 2020 Jul 15;25(14):3224. doi: 10.3390/molecules25143224. [PubMed:32679716 ]
Li N, Yi Z, Wang Y, Zhang Q, Zhong T, Qiu Y, Wu Z, Tang X: Differential proteomic analysis of HL60 cells treated with secalonic acid F reveals caspase 3-induced cleavage of Rho GDP dissociation inhibitor 2. Oncol Rep. 2012 Dec;28(6):2016-22. doi: 10.3892/or.2012.2062. Epub 2012 Sep 27. [PubMed:23023390 ]
Zeng R, Luo S, Shi Y: [Allelopathic effects of secalonic acid F produced by Aspergillus japonicus on Zea mays]. Ying Yong Sheng Tai Xue Bao. 2004 Jan;15(1):145-8. [PubMed:15139208 ]
LOTUS database [Link]

Showing NP-Card for 10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate (NP0282084)

MOL for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

3D MOL for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

3D SDF for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

3D-SDF for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

PDB for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

3D PDB for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

SMILES for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

INCHI for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

Structure for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)

3D Structure for NP0282084 (10a,10'a-dimethyl (5r,5's,6s,6's,10ar,10'ar)-1,1',5,5',9,9'-hexahydroxy-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthene]-10a,10'a-dicarboxylate)