NP-MRD: Showing NP-Card for Purpurquinone A (NP0010274)

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Record Information

Version

1.0

Created at

2021-01-05 19:51:00 UTC

Updated at

2021-07-15 17:05:38 UTC

NP-MRD ID

NP0010274

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurquinone A

Provided By

NPAtlas

Description

Purpurquinone A 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. Purpurquinone A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Purpurquinone A is found in Penicillium and Talaromyces purpureogenus. It was first documented in 2011 (PMID: 21879714). Based on a literature review very few articles have been published on Purpurquinone A (PMID: 34383398) (PMID: 34383397) (PMID: 34383396) (PMID: 34384147).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107363D          

 50 52  0  0  0  0            999 V2000
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    6.4794   -0.3711   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242107363D          

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    2.4657   -2.6968   -0.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -0.4137   -1.7348 H   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30  4  1  0  0  0  0
 26  6  1  0  0  0  0
 22 15  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  0  0  0  0
  5 36  1  0  0  0  0
  7 37  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 18 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  0  0  0  0
 27 48  1  0  0  0  0
 28 49  1  1  0  0  0
 29 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C(C(=O)O[C@@]2(C(=O)C([H])=C3C([H])=C(O[C@]([H])(O[H])[C@]3(O[H])C2=O)C(\[H])=C(/[H])C([H])([H])[H])C([H])([H])[H])C(O[H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c1-4-5-13-7-11-8-15(24)20(3,18(26)21(11,28)19(27)29-13)30-17(25)16-10(2)6-12(22)9-14(16)23/h4-9,19,22-23,27-28H,1-3H3/b5-4+/t19-,20+,21+/m0/s1

> <INCHI_KEY>
AWAFQUDYYMTSLY-QWOQCBQGSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.382

> <EXACT_MASS>
416.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.96590012121284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(1E)-prop-1-en-1-yl]-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.152756107333334

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.209954691158732

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.675716169749302

> <JCHEM_PKA_STRONGEST_BASIC>
-4.003825515757616

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
106.83689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(1E)-prop-1-en-1-yl]-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    7.8449    0.0031   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794   -0.3711   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    0.4981   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842    0.0768   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4406    0.9411    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081    0.5500    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252    1.4068    1.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    1.0513    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    1.8418    2.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -0.3040    1.4975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6129   -1.1486    2.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9701   -0.2866    1.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.3866   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054    1.0343   -0.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571    0.2913   -0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519    0.9484   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    1.7413   -2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7178    0.8604   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    0.1343   -0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9418    0.0140   -1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0787   -0.5263    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -0.4410    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000   -1.0926    1.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.9596    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248   -1.5490   -0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305   -0.8791    0.8007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0843   -1.4725    2.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5192   -1.6157   -0.2760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9814   -1.3949   -1.5286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8810   -1.2349   -0.1963 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6180   -0.7279   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176    0.1521   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027    0.9716   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1400   -1.3917   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9643    1.5174   -0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532    1.9713    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418    2.4573    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -0.8350    3.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -2.2205    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707   -1.0021    3.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850    2.2687   -3.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    1.1528   -2.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289    2.5749   -1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203    1.3780   -2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5555    0.7067   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6821   -1.1200    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -1.6368    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0655   -1.6101    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657   -2.6968   -0.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -0.4137   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  6
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 10 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30  4  1  0
 26  6  1  0
 22 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  5 36  1  0
  7 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 27 48  1  0
 28 49  1  1
 29 50  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       7.845   0.003  -1.454  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.479  -0.371  -1.009  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.637   0.498  -0.479  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.284   0.077  -0.050  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.441   0.941   0.479  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.108   0.550   0.908  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.225   1.407   1.387  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.117   1.051   1.825  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.856   1.842   2.474  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.649  -0.304   1.498  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.613  -1.149   2.778  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.970  -0.287   1.060  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.439   0.387  -0.055  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.605   1.034  -0.727  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.857   0.291  -0.360  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.352   0.948  -1.460  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.462   1.741  -2.323  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.718   0.860  -1.759  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.591   0.134  -0.987  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.942   0.014  -1.235  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.079  -0.526   0.124  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.734  -0.441   0.420  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.200  -1.093   1.525  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.284  -0.960   0.547  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.125  -1.549  -0.417  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.730  -0.879   0.801  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.084  -1.472   2.020  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.519  -1.616  -0.276  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.981  -1.395  -1.529  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.881  -1.235  -0.196  0.00  0.00           O+0
HETATM   31  H   UNK     0       8.618  -0.728  -1.081  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.918   0.152  -2.546  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.103   0.972  -0.950  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.140  -1.392  -1.113  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.964   1.517  -0.371  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.753   1.971   0.596  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.542   2.457   1.452  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.220  -0.835   3.435  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.545  -2.220   2.485  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.571  -1.002   3.329  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.085   2.269  -3.104  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.653   1.153  -2.799  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.029   2.575  -1.731  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.120   1.378  -2.630  0.00  0.00           H+0
HETATM   45  H   UNK     0      -8.556   0.707  -0.809  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.682  -1.120   0.790  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.821  -1.637   2.114  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.066  -1.610   2.037  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.466  -2.697  -0.041  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.082  -0.414  -1.735  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   24                                             
CONECT   11   10   38   39   40                                             
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   41   42   43                                             
CONECT   18   16   19   44                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   45                                                       
CONECT   21   19   22   46                                                  
CONECT   22   21   23   15                                                  
CONECT   23   22   47                                                       
CONECT   24   10   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28    6                                             
CONECT   27   26   48                                                       
CONECT   28   26   29   30   49                                             
CONECT   29   28   50                                                       
CONECT   30   28    4                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   27                                                            
CONECT   49   28                                                            
CONECT   50   29                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    7.8449    0.0031   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794   -0.3711   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6369    0.4981   -0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842    0.0768   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4406    0.9411    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081    0.5500    0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252    1.4068    1.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    1.0513    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    1.8418    2.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -0.3040    1.4975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6129   -1.1486    2.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9701   -0.2866    1.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.3866   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054    1.0343   -0.7266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571    0.2913   -0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519    0.9484   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    1.7413   -2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7178    0.8604   -1.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5911    0.1343   -0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9418    0.0140   -1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0787   -0.5263    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -0.4410    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000   -1.0926    1.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.9596    0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248   -1.5490   -0.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305   -0.8791    0.8007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0843   -1.4725    2.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5192   -1.6157   -0.2760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9814   -1.3949   -1.5286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8810   -1.2349   -0.1963 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6180   -0.7279   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176    0.1521   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1027    0.9716   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1400   -1.3917   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9643    1.5174   -0.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532    1.9713    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418    2.4573    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -0.8350    3.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -2.2205    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707   -1.0021    3.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850    2.2687   -3.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    1.1528   -2.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289    2.5749   -1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1203    1.3780   -2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5555    0.7067   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6821   -1.1200    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -1.6368    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0655   -1.6101    2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657   -2.6968   -0.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -0.4137   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  6
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 10 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30  4  1  0
 26  6  1  0
 22 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  5 36  1  0
  7 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 27 48  1  0
 28 49  1  1
 29 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₉

Average Mass

416.3820 Da

Monoisotopic Mass

416.11073 Da

IUPAC Name

(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(1E)-prop-1-en-1-yl]-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

(1S,7R,8aS)-1,8a-dihydroxy-7-methyl-6,8-dioxo-3-[(1E)-prop-1-en-1-yl]-1H-isochromen-7-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

C\C=C\C1=CC2=CC(=O)[C@@](C)(OC(=O)C3=C(O)C=C(O)C=C3C)C(=O)[C@@]2(O)[C@@H](O)O1

InChI Identifier

InChI=1S/C21H20O9/c1-4-5-13-7-11-8-15(24)20(3,18(26)21(11,28)19(27)29-13)30-17(25)16-10(2)6-12(22)9-14(16)23/h4-9,19,22-23,27-28H,1-3H3/b5-4+/t19-,20+,21+/m0/s1

InChI Key

AWAFQUDYYMTSLY-QWOQCBQGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium	NPAtlas	21879714
Penicillium purpurogenum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium purpurogenum JS03-21	KNApSAcK Database	22123792

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
Benzoic acid or derivatives
M-cresol
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Toluene
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Cyclic ketone
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

enone (CHEBI:69469 )
polyketide (CHEBI:69469 )
benzoate ester (CHEBI:69469 )
isochromenes (CHEBI:69469 )
azaphilone (CHEBI:69469 )

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	2.45	ALOGPS
logP	3.15	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.84 m³·mol⁻¹	ChemAxon
Polarizability	39.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002067

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053730

Chemspider ID

26619075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54672171

PDB ID

Not Available

ChEBI ID

69469

Good Scents ID

Not Available

References

General References

Wang H, Wang Y, Wang W, Fu P, Liu P, Zhu W: Anti-influenza virus polyketides from the acid-tolerant fungus Penicillium purpurogenum JS03-21. J Nat Prod. 2011 Sep 23;74(9):2014-8. doi: 10.1021/np2004769. Epub 2011 Aug 31. [PubMed:21879714 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
Authors unspecified: Ponesimod. 2012. [PubMed:34383396 ]
Lee J, Cho Y, Choi KH, Hwang I, Oh YL: Metastatic leiomyosarcoma of the thyroid gland: cytologic findings and differential diagnosis. J Pathol Transl Med. 2021 Aug 13. pii: jptm.2021.06.23. doi: 10.4132/jptm.2021.06.23. [PubMed:34384147 ]

Showing NP-Card for Purpurquinone A (NP0010274)

MOL for NP0010274 (Purpurquinone A)

3D MOL for NP0010274 (Purpurquinone A)

3D SDF for NP0010274 (Purpurquinone A)

3D-SDF for NP0010274 (Purpurquinone A)

PDB for NP0010274 (Purpurquinone A)

3D PDB for NP0010274 (Purpurquinone A)

SMILES for NP0010274 (Purpurquinone A)

INCHI for NP0010274 (Purpurquinone A)

Structure for NP0010274 (Purpurquinone A)

3D Structure for NP0010274 (Purpurquinone A)