NP-MRD: Showing NP-Card for (5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate (NP0317850)

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Record Information

Version

2.0

Created at

2022-09-11 17:58:43 UTC

Updated at

2022-09-11 17:58:44 UTC

NP-MRD ID

NP0317850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

Description

(6R,7R)-3-[(1E)-3-[(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxo-5,6,7,8-tetrahydro-1H-isochromen-5-ylidene]prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6,7,8-tetrahydro-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. (5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate is found in Hypoxylon rutilum. Based on a literature review very few articles have been published on (6R,7R)-3-[(1E)-3-[(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxo-5,6,7,8-tetrahydro-1H-isochromen-5-ylidene]prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6,7,8-tetrahydro-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219582D          

 60 65  0  0  1  0            999 V2000
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.4750    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   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
   -5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -1.6500    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
  2  3  2  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
  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
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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
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 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
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 47 60  1  0  0  0  0
 38 60  1  0  0  0  0
M  END

     RDKit          3D

100105  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309112219582D          

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M  END
> <DATABASE_ID>
NP0317850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C=C\C1=CC2=C(CO1)C(=O)[C@@](C)(OC(=O)C1=C(C)C=C(O)C=C1O)C(=O)\C2=C/C=C/C1=CC2=C(CO1)C(=O)[C@](C)(O)[C@@H](C2)OC(=O)C1=C(C)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H40O16/c1-21-12-25(46)16-33(48)36(21)41(53)59-35-15-24-14-27(57-19-31(24)38(50)43(35,4)55)8-6-10-29-30-18-28(9-7-11-56-23(3)45)58-20-32(30)40(52)44(5,39(29)51)60-42(54)37-22(2)13-26(47)17-34(37)49/h6-10,12-14,16-18,35,46-49,55H,11,15,19-20H2,1-5H3/b8-6+,9-7+,29-10-/t35-,43-,44+/m1/s1

> <INCHI_KEY>
OQKLHNURLMVVRL-DJWCDVQHSA-N

> <FORMULA>
C44H40O16

> <MOLECULAR_WEIGHT>
824.788

> <EXACT_MASS>
824.231635208

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
82.58186363304279

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2E)-3-[(6R,7R)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6,7,8-tetrahydro-1H-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-5,6,7,8-tetrahydro-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_LOGP>
6.004029805333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.978921134710973

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.388711852080723

> <JCHEM_PKA_STRONGEST_BASIC>
-3.993452160067034

> <JCHEM_POLAR_SURFACE_AREA>
249.71999999999994

> <JCHEM_REFRACTIVITY>
219.4829

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2E)-3-[(6R,7R)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1H-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -10.669 -12.320   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.669   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.992   1.180   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.012   1.180   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.539   2.627   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -9.055   2.894   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.549   3.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.076   5.254   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.592   5.521   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.086   6.433   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.569   6.166   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.579   7.346   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.043   4.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.032   3.539   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.506   2.092   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.528   0.677   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.518  -1.037   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28                                                            
CONECT   30   16   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   10   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   60                                                  
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44   48   60                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   58                                                  
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57   51   59                                                  
CONECT   59   58                                                            
CONECT   60   47   38                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  130    0
END

View in JSmol

Synonyms

Value	Source
(6R,7R)-3-[(1E)-3-[(5Z,7S)-3-[(1E)-3-(Acetyloxy)prop-1-en-1-yl]-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxo-5,6,7,8-tetrahydro-1H-isochromen-5-ylidene]prop-1-en-1-yl]-7-hydroxy-7-methyl-8-oxo-5,6,7,8-tetrahydro-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoic acid	Generator

Chemical Formula

C₄₄H₄₀O₁₆

Average Mass

824.7880 Da

Monoisotopic Mass

824.23164 Da

IUPAC Name

(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2E)-3-[(6R,7R)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6,7,8-tetrahydro-1H-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-5,6,7,8-tetrahydro-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

(5Z,7S)-3-[(1E)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2E)-3-[(6R,7R)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1H-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C=C\C1=CC2=C(CO1)C(=O)[C@@](C)(OC(=O)C1=C(C)C=C(O)C=C1O)C(=O)\C2=C/C=C/C1=CC2=C(CO1)C(=O)[C@](C)(O)[C@@H](C2)OC(=O)C1=C(C)C=C(O)C=C1O

InChI Identifier

InChI=1S/C44H40O16/c1-21-12-25(46)16-33(48)36(21)41(53)59-35-15-24-14-27(57-19-31(24)38(50)43(35,4)55)8-6-10-29-30-18-28(9-7-11-56-23(3)45)58-20-32(30)40(52)44(5,39(29)51)60-42(54)37-22(2)13-26(47)17-34(37)49/h6-10,12-14,16-18,35,46-49,55H,11,15,19-20H2,1-5H3/b8-6+,9-7+,29-10-/t35-,43-,44+/m1/s1

InChI Key

OQKLHNURLMVVRL-DJWCDVQHSA-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
Hypoxylon rutilum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoate ester
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
M-cresol
Resorcinol
Benzoyl
Toluene
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Acyloin
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Tertiary alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
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	6	ChemAxon
pKa (Strongest Acidic)	8.39	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	249.72 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	219.48 m³·mol⁻¹	ChemAxon
Polarizability	82.58 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163187280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate (NP0317850)

MOL for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

3D MOL for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

3D SDF for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

3D-SDF for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

PDB for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

3D PDB for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

SMILES for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

INCHI for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

Structure for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)

3D Structure for NP0317850 ((5z,7s)-3-[(1e)-3-(acetyloxy)prop-1-en-1-yl]-5-[(2e)-3-[(6r,7r)-6-(2,4-dihydroxy-6-methylbenzoyloxy)-7-hydroxy-7-methyl-8-oxo-5,6-dihydro-1h-isochromen-3-yl]prop-2-en-1-ylidene]-7-methyl-6,8-dioxo-1h-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate)