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Showing NP-Card for (8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one (NP0322889)

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Record Information
Version2.0
Created at2022-09-12 01:56:58 UTC
Updated at2022-09-12 01:56:59 UTC
NP-MRD IDNP0322889
Secondary Accession NumbersNone
Natural Product Identification
Common Name(8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one
DescriptionInterruptin E belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. (8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one is found in Cyclosorus interruptus. Based on a literature review very few articles have been published on Interruptin E.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)


  Mrv1652309122203562D          

 31 35  0  0  1  0            999 V2000
    2.8429    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455    3.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996   -1.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8904   -0.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4720    0.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046   -0.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8166   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3492   -0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0699   -1.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253   -1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  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
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 22 31  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
Download

3D MOL for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)

Download
3D SDF for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)

  Mrv1652309122203562D          

 31 35  0  0  1  0            999 V2000
    2.8429    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455    3.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996   -1.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8904   -0.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4720    0.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046   -0.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8166   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3492   -0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0699   -1.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253   -1.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  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
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 22 31  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2O[C@](O)(CC3=CC=CC=C3)[C@@H](O)C2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H20O6/c1-14-21(27)19-17(16-10-6-3-7-11-16)12-18(26)30-23(19)20-22(14)31-25(29,24(20)28)13-15-8-4-2-5-9-15/h2-12,24,27-29H,13H2,1H3/t24-,25+/m0/s1

> <INCHI_KEY>
MVZOBERUULSCEN-LOSJGSFVSA-N

> <FORMULA>
C25H20O6

> <MOLECULAR_WEIGHT>
416.429

> <EXACT_MASS>
416.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.704440685357014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8R,9S)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-2H,8H,9H-furo[2,3-h]chromen-2-one

> <JCHEM_LOGP>
4.0441512390000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.683379187584592

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.689070438656157

> <JCHEM_PKA_STRONGEST_BASIC>
-4.078093379363108

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
123.7192

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(8R,9S)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9H-furo[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)
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PDB for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.307   4.649   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.122   3.484   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.662   3.532   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.389   4.889   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.578   6.198   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.039   6.150   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.689   4.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.039  -1.998   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.262  -1.399   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.348   0.353   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.342  -0.823   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.858  -0.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.852  -1.726   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.330  -3.175   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.815  -3.448   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.821  -2.272   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   10    5   18                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18                                                            
CONECT   20    4   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

Download
3D PDB for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)
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SMILES for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)
CC1=C2O[C@](O)(CC3=CC=CC=C3)[C@@H](O)C2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O
Download
INCHI for NP0322889 ((8r,9s)-8-benzyl-5,8,9-trihydroxy-6-methyl-4-phenyl-9h-furo[2,3-h]chromen-2-one)
InChI=1S/C25H20O6/c1-14-21(27)19-17(16-10-6-3-7-11-16)12-18(26)30-23(19)20-22(14)31-25(29,24(20)28)13-15-8-4-2-5-9-15/h2-12,24,27-29H,13H2,1H3/t24-,25+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC25H20O6
Average Mass416.4290 Da
Monoisotopic Mass416.12599 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1=C2O[C@](O)(CC3=CC=CC=C3)[C@@H](O)C2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O
InChI Identifier
InChI=1S/C25H20O6/c1-14-21(27)19-17(16-10-6-3-7-11-16)12-18(26)30-23(19)20-22(14)31-25(29,24(20)28)13-15-8-4-2-5-9-15/h2-12,24,27-29H,13H2,1H3/t24-,25+/m0/s1
InChI KeyMVZOBERUULSCEN-LOSJGSFVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cyclosorus interruptusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassDiarylheptanoids  
Sub ClassLinear diarylheptanoids  
Direct ParentLinear diarylheptanoids  
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
    • 

  • 4-phenylcoumarin
    • 

  • Neoflavonoid skeleton
    • 

  • Angular furanocoumarin
    • 

  • Furanocoumarin
    • 

  • Coumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Coumaran
    • 

  • Pyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Hemiacetal
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9917331  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11742627  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]