NP-MRD: Showing NP-Card for Sculezonone B (NP0003234)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:10 UTC

Updated at

2021-07-15 16:45:52 UTC

NP-MRD ID

NP0003234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sculezonone B

Provided By

NPAtlas

Description

Sculezonone B is found in Penicillium sp. It was first documented in 2000 (PMID: 10757733). Based on a literature review very few articles have been published on 2,4,5,7,9-pentahydroxy-8-methoxy-6-methyl-2-(2-methyl-3-oxobutan-2-yl)-2,3-dihydro-1H-phenalene-1,3-dione (PMID: 12056892).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

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M  END

     RDKit          3D

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  Mrv1652306242117463D          

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  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 28  1  0  0  0  0
 28 29  2  0  0  0  0
 16  3  1  0  0  0  0
 28  6  1  0  0  0  0
 15  7  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  5 33  1  0  0  0  0
 10 34  1  0  0  0  0
 12 35  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 17 39  1  0  0  0  0
 21 40  1  0  0  0  0
 23 41  1  0  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)[C@](O[H])(C(=O)C3=C2C(=C(O[H])C(OC([H])([H])[H])=C3O[H])C(=C1O[H])C([H])([H])[H])C(C(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O9/c1-6-8-9-10(13(23)12(6)22)17(26)20(28,19(3,4)7(2)21)18(27)11(9)15(25)16(29-5)14(8)24/h22-25,28H,1-5H3/t20-/m0/s1

> <INCHI_KEY>
NKDAVCHIYATDKS-UHFFFAOYSA-N

> <FORMULA>
C20H20O9

> <MOLECULAR_WEIGHT>
404.371

> <EXACT_MASS>
404.110732224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.04051714490026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2,4,5,7,9-pentahydroxy-8-methoxy-6-methyl-2-(2-methyl-3-oxobutan-2-yl)-2,3-dihydro-1H-phenalene-1,3-dione

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
3.1395022256666665

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.369857503736165

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.472450719722858

> <JCHEM_PKA_STRONGEST_BASIC>
-4.698518460485052

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
101.15569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,4,5,7,9-pentahydroxy-8-methoxy-6-methyl-2-(2-methyl-3-oxobutan-2-yl)phenalene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -4.3669    3.3145    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    2.7146   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    1.7309   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835    2.0597   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691    3.3975    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428    1.0465    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -0.2841    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366   -1.2738    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -2.6097    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296   -3.5835    1.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -2.8958    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -4.2205    0.0428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -1.9230   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8524   -2.2939   -0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062   -0.6104   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    0.4281   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    0.0974   -1.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.0228    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0225   -1.8616    1.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.3307    0.9114 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8365    0.6030    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692    0.3105   -0.3568 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8738   -0.0766   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    1.6808   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.6381   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707   -0.4769    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0171   -1.5885   -1.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903    1.3449    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    2.4734    1.3801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0459    3.0356    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3185    4.4163   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3874    2.9156   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    3.8233    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -4.5618    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315   -4.9725    0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.9630   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9287   -3.4231   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083   -2.0678   -1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    0.7884   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0778    1.5753    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.1629   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    0.6477   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -1.0705   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197    1.6339   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882    2.3887   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607    2.0644    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537    0.5992    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360   -0.9553    1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9451   -0.8849    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  1
 25 26  1  0
 25 27  2  0
 20 28  1  0
 28 29  2  0
 16  3  1  0
 28  6  1  0
 15  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 26 47  1  0
 26 48  1  0
 26 49  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      -4.367   3.314   0.010  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.440   2.715  -0.900  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.559   1.731  -0.496  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.284   2.060  -0.011  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.969   3.397   0.037  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.443   1.046   0.380  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.830  -0.284   0.301  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.037  -1.274   0.696  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.366  -2.610   0.610  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.530  -3.583   1.016  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.619  -2.896   0.131  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.025  -4.221   0.043  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.509  -1.923  -0.273  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.852  -2.294  -0.783  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.106  -0.610  -0.185  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.936   0.428  -0.572  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.190   0.097  -1.048  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.374  -1.023   1.201  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.022  -1.862   1.845  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.973   0.331   0.911  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.837   0.603   1.968  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.769   0.311  -0.357  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.874  -0.077  -1.517  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.333   1.681  -0.654  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.912  -0.638  -0.254  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.971  -0.477   0.774  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.017  -1.589  -1.017  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.890   1.345   0.910  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.149   2.473   1.380  0.00  0.00           O+0
HETATM   30  H   UNK     0      -4.046   3.036   1.034  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.319   4.416  -0.106  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.387   2.916  -0.164  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.157   3.823   0.322  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.410  -4.562   1.022  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.432  -4.973   0.318  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.682  -1.963  -0.114  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.929  -3.423  -0.738  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.008  -2.068  -1.848  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.842   0.788  -1.345  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.078   1.575   2.006  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.544  -0.163  -2.411  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.069   0.648  -1.682  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.407  -1.071  -1.366  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.920   1.634  -1.606  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.488   2.389  -0.843  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.961   2.064   0.178  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.154   0.599   1.014  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.636  -0.955   1.726  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.945  -0.885   0.456  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   33                                                       
CONECT    6    4    7   28                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   34                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11   35                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13   36   37   38                                             
CONECT   15   13   16    7                                                  
CONECT   16   15   17    3                                                  
CONECT   17   16   39                                                       
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   28                                             
CONECT   21   20   40                                                       
CONECT   22   20   23   24   25                                             
CONECT   23   22   41   42   43                                             
CONECT   24   22   44   45   46                                             
CONECT   25   22   26   27                                                  
CONECT   26   25   47   48   49                                             
CONECT   27   25                                                            
CONECT   28   20   29    6                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    5                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   17                                                            
CONECT   40   21                                                            
CONECT   41   23                                                            
CONECT   42   23                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
CONECT   47   26                                                            
CONECT   48   26                                                            
CONECT   49   26                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

RDKit          3D

49 51  0  0  0  0  0  0  0  0999 V2000
   -4.3669    3.3145    0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    2.7146   -0.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    1.7309   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835    2.0597   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691    3.3975    0.0367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428    1.0465    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -0.2841    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366   -1.2738    0.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3656   -2.6097    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296   -3.5835    1.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -2.8958    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -4.2205    0.0428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -1.9230   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8524   -2.2939   -0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062   -0.6104   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    0.4281   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    0.0974   -1.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741   -1.0228    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0225   -1.8616    1.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.3307    0.9114 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8365    0.6030    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692    0.3105   -0.3568 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8738   -0.0766   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    1.6808   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.6381   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707   -0.4769    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0171   -1.5885   -1.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903    1.3449    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    2.4734    1.3801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0459    3.0356    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3185    4.4163   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3874    2.9156   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    3.8233    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -4.5618    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315   -4.9725    0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.9630   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9287   -3.4231   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0083   -2.0678   -1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    0.7884   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0778    1.5753    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.1629   -2.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    0.6477   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -1.0705   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197    1.6339   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882    2.3887   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9607    2.0644    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537    0.5992    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6360   -0.9553    1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9451   -0.8849    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  1
 25 26  1  0
 25 27  2  0
 20 28  1  0
 28 29  2  0
 16  3  1  0
 28  6  1  0
 15  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 26 47  1  0
 26 48  1  0
 26 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Sculezonone-b	MeSH

Chemical Formula

C₂₀H₂₀O₉

Average Mass

404.3710 Da

Monoisotopic Mass

404.11073 Da

IUPAC Name

(2S)-2,4,5,7,9-pentahydroxy-8-methoxy-6-methyl-2-(2-methyl-3-oxobutan-2-yl)-2,3-dihydro-1H-phenalene-1,3-dione

Traditional Name

(2S)-2,4,5,7,9-pentahydroxy-8-methoxy-6-methyl-2-(2-methyl-3-oxobutan-2-yl)phenalene-1,3-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C3C(=C(O)C(O)=C2C)C(=O)C(O)(C(=O)C3=C1O)C(C)(C)C(C)=O

InChI Identifier

InChI=1S/C20H20O9/c1-6-8-9-10(13(23)12(6)22)17(26)20(28,19(3,4)7(2)21)18(27)11(9)15(25)16(29-5)14(8)24/h22-25,28H,1-5H3

InChI Key

NKDAVCHIYATDKS-UHFFFAOYSA-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 sp.	NPAtlas	10757733

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenalanes. These are aromatic hydrocarbons containing a cyclohexene ring fused to both benzenes of a naphthalene ring system, so as to form a triad.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenalanes

Sub Class

Not Available

Direct Parent

Phenalanes

Alternative Parents

Substituents

Phenalane
2-naphthol
1-naphthol
Naphthalene
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
Beta-hydroxy ketone
Acyloin
Vinylogous acid
Tertiary alcohol
Ketone
Ether
Polyol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.96	ALOGPS
logP	3.14	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.16 m³·mol⁻¹	ChemAxon
Polarizability	39.04 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

NPA006234

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8651737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10476327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Komatsu K, Shigemori H, Mikami Y, Kobayashi J: Sculezonones A and B, two metabolites possessing a phenalenone skeleton from a marine-derived fungus Penicillium species. J Nat Prod. 2000 Mar;63(3):408-9. doi: 10.1021/np990452t. [PubMed:10757733 ]
Perpelescu M, Kobayashi J, Furuta M, Ito Y, Izuta S, Takemura M, Suzuki M, Yoshida S: Novel phenalenone derivatives from a marine-derived fungus exhibit distinct inhibition spectra against eukaryotic DNA polymerases. Biochemistry. 2002 Jun 18;41(24):7610-6. doi: 10.1021/bi020115a. [PubMed:12056892 ]

Showing NP-Card for Sculezonone B (NP0003234)

MOL for NP0003234 (Sculezonone B)

3D MOL for NP0003234 (Sculezonone B)

3D SDF for NP0003234 (Sculezonone B)

3D-SDF for NP0003234 (Sculezonone B)

PDB for NP0003234 (Sculezonone B)

3D PDB for NP0003234 (Sculezonone B)

SMILES for NP0003234 (Sculezonone B)

INCHI for NP0003234 (Sculezonone B)

Structure for NP0003234 (Sculezonone B)

3D Structure for NP0003234 (Sculezonone B)