NP-MRD: Showing NP-Card for Dihydroisoustilaginoidin A (NP0003946)

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Record Information

Version

2.0

Created at

2020-12-09 01:29:00 UTC

Updated at

2021-07-15 16:47:48 UTC

NP-MRD ID

NP0003946

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroisoustilaginoidin A

Provided By

NPAtlas

Description

Dihydroisoustilaginoidin A is found in Ustilaginoidea virens and Verticillium. Dihydroisoustilaginoidin A was first documented in 1975 (PMID: 1171848). Based on a literature review very few articles have been published on 4,5,6-trihydroxy-2-methyl-9-{5,6,8-trihydroxy-2-methyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl}-8H-cyclohexa[g]chromen-8-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 58 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117513D          

 58 63  0  0  0  0            999 V2000
    3.9660   -1.7034   -4.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151   -0.7039   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7752    2.8844   -1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722    0.4953   -1.1484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7508   -0.8570   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -1.8591   -1.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539    0.4807    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852   -0.3438    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -0.0602   -0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690   -0.9113   -1.9984 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947   -2.6662   -3.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955   -1.3322   -5.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0531   -1.9298   -4.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867    0.6754   -3.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6784    4.2853    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0297   -3.1866    3.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838   -4.4294    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497   -5.4537    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8685    1.2096   -2.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8144    3.2606   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629    2.9754   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385    3.4755   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893    0.8031   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1318    0.4795   -1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.2655   -0.0809 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  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  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  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
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 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 15 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38  2  1  0  0  0  0
 37  6  1  0  0  0  0
 35  9  1  0  0  0  0
 28 16  1  0  0  0  0
 28 22  1  0  0  0  0
 33 25  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  3 42  1  0  0  0  0
  5 43  1  0  0  0  0
  8 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 46  1  0  0  0  0
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 19 48  1  0  0  0  0
 21 49  1  0  0  0  0
 24 50  1  0  0  0  0
 27 51  1  0  0  0  0
 30 52  1  6  0  0  0
 31 53  1  0  0  0  0
 31 54  1  0  0  0  0
 31 55  1  0  0  0  0
 32 56  1  0  0  0  0
 32 57  1  0  0  0  0
 36 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=O)C(=C2C([H])=C3OC(=C([H])C(O[H])=C3C(O[H])=C12)C([H])([H])[H])C1=C(O[H])C([H])=C(O[H])C2=C(O[H])C3=C(O[C@]([H])(C([H])([H])[H])C([H])([H])C3=O)C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C28H20O10/c1-9-3-13(29)25-19(37-9)5-11-21(15(31)7-17(33)23(11)27(25)35)22-12-6-20-26(14(30)4-10(2)38-20)28(36)24(12)18(34)8-16(22)32/h3,5-8,10,29,32-36H,4H2,1-2H3/t10-/m1/s1

> <INCHI_KEY>
IIKCGQWDQVJPMD-UHFFFAOYSA-N

> <FORMULA>
C28H20O10

> <MOLECULAR_WEIGHT>
516.458

> <EXACT_MASS>
516.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
51.69140316219828

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,6-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl]-8H-cyclohexa[g]chromen-8-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.3171271369999995

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.67077795350015

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.99082458234913

> <JCHEM_PKA_STRONGEST_BASIC>
2.6248790123892154

> <JCHEM_POLAR_SURFACE_AREA>
173.97999999999996

> <JCHEM_REFRACTIVITY>
141.40169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,6-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2H,3H-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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   -3.1003   -2.1984    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7752    2.8844   -1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722    0.4953   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6784    4.2853    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    2.7942    4.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.1866    3.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9497   -5.4537    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055   -3.5942   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8685    1.2096   -2.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3370   -1.2655   -0.0809 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
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 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
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 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  2  0
 15 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38  2  1  0
 37  6  1  0
 35  9  1  0
 28 16  1  0
 28 22  1  0
 33 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
  8 44  1  0
 11 45  1  0
 12 46  1  0
 18 47  1  0
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 24 50  1  0
 27 51  1  0
 30 52  1  6
 31 53  1  0
 31 54  1  0
 31 55  1  0
 32 56  1  0
 32 57  1  0
 36 58  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       3.966  -1.703  -4.094  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.815  -0.704  -2.971  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.560   0.435  -2.950  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.424   1.375  -1.901  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.168   2.493  -1.898  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.518   1.112  -0.897  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.304   1.978   0.189  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.003   3.104   0.261  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.369   1.654   1.178  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.123   2.469   2.262  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.810   3.649   2.400  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.189   2.142   3.246  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.481   0.966   3.140  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.370   0.628   4.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.714   0.140   2.063  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.016  -1.122   1.865  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.469  -2.319   2.356  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.658  -2.336   3.083  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.258  -3.466   2.119  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.426  -3.409   1.399  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.195  -4.541   1.134  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.898  -2.202   0.895  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.100  -2.198   0.163  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.777  -3.368  -0.038  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.517  -0.986  -0.309  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.816   0.188  -0.093  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.625   0.128   0.643  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.169  -1.075   1.136  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.237   1.396  -0.565  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.272   1.471  -1.513  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.775   2.884  -1.564  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.372   0.495  -1.148  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.751  -0.857  -1.095  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.223  -1.859  -1.678  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.654   0.481   1.085  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.885  -0.344   0.011  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.801  -0.060  -0.987  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.969  -0.911  -1.998  0.00  0.00           O+0
HETATM   39  H   UNK     0       3.495  -2.666  -3.818  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.495  -1.332  -5.004  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.053  -1.930  -4.255  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.287   0.675  -3.728  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.257   3.242  -1.334  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.179   3.899   0.748  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.678   4.285   3.164  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.010   2.794   4.090  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.030  -3.187   3.461  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.084  -4.429   2.500  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.950  -5.454   1.447  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.606  -3.594  -0.493  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.059   1.032   0.825  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.869   1.210  -2.518  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.814   3.261  -0.507  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.763   2.975  -2.059  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.038   3.475  -2.164  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.789   0.803  -0.189  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.132   0.480  -1.936  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.337  -1.266  -0.081  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3   38                                                  
CONECT    3    2    4   42                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   43                                                       
CONECT    6    4    7   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   44                                                       
CONECT    9    7   10   35                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   45                                                       
CONECT   12   10   13   46                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   35                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   47                                                       
CONECT   19   17   20   48                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   49                                                       
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   50                                                       
CONECT   25   23   26   33                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28   51                                                  
CONECT   28   27   16   22                                                  
CONECT   29   26   30                                                       
CONECT   30   29   31   32   52                                             
CONECT   31   30   53   54   55                                             
CONECT   32   30   33   56   57                                             
CONECT   33   32   34   25                                                  
CONECT   34   33                                                            
CONECT   35   15   36    9                                                  
CONECT   36   35   37   58                                                  
CONECT   37   36   38    6                                                  
CONECT   38   37    2                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    3                                                            
CONECT   43    5                                                            
CONECT   44    8                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   21                                                            
CONECT   50   24                                                            
CONECT   51   27                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   31                                                            
CONECT   55   31                                                            
CONECT   56   32                                                            
CONECT   57   32                                                            
CONECT   58   36                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

RDKit          3D

58 63  0  0  0  0  0  0  0  0999 V2000
    3.9660   -1.7034   -4.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151   -0.7039   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    0.4348   -2.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236    1.3754   -1.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1675    2.4934   -1.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5175    1.1119   -0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3041    1.9775    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033    3.1040    0.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685    1.6538    1.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4690    2.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8099    3.6486    2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1886    2.1418    3.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    0.9657    3.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    0.6282    3.9996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140    0.1401    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160   -1.1224    1.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685   -2.3193    2.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -2.3364    3.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2579   -3.4659    2.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255   -3.4090    1.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -4.5412    1.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976   -2.2016    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003   -2.1984    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7769   -3.3682   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167   -0.9857   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8159    0.1878   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6245    0.1280    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687   -1.0750    1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    1.3964   -0.5646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2718    1.4714   -1.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7752    2.8844   -1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722    0.4953   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508   -0.8570   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -1.8591   -1.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539    0.4807    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852   -0.3438    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -0.0602   -0.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690   -0.9113   -1.9984 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947   -2.6662   -3.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955   -1.3322   -5.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0531   -1.9298   -4.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867    0.6754   -3.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569    3.2424   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791    3.8987    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6784    4.2853    3.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    2.7942    4.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.1866    3.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838   -4.4294    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497   -5.4537    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055   -3.5942   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588    1.0316    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685    1.2096   -2.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8144    3.2606   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629    2.9754   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385    3.4755   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893    0.8031   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1318    0.4795   -1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.2655   -0.0809 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  2  0
 15 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38  2  1  0
 37  6  1  0
 35  9  1  0
 28 16  1  0
 28 22  1  0
 33 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
  8 44  1  0
 11 45  1  0
 12 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 24 50  1  0
 27 51  1  0
 30 52  1  6
 31 53  1  0
 31 54  1  0
 31 55  1  0
 32 56  1  0
 32 57  1  0
 36 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₂₀O₁₀

Average Mass

516.4580 Da

Monoisotopic Mass

516.10565 Da

IUPAC Name

4,5,6-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl]-8H-cyclohexa[g]chromen-8-one

Traditional Name

4,5,6-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2H,3H-naphtho[2,3-b]pyran-9-yl]cyclohexa[g]chromen-8-one

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C2=C(O1)C=C1C(C(O)=CC(O)=C1C1=C3C=C4OC(C)=CC(O)=C4C(O)=C3C(O)=CC1=O)=C2O

InChI Identifier

InChI=1S/C28H20O10/c1-9-3-13(29)25-19(37-9)5-11-21(15(31)7-17(33)23(11)27(25)35)22-12-6-20-26(14(30)4-10(2)38-20)28(36)24(12)18(34)8-16(22)32/h3,5-8,10,29,32-36H,4H2,1-2H3

InChI Key

IIKCGQWDQVJPMD-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
Ustilaginoidea virens	LOTUS Database	35616633
Verticillium	NPAtlas	1171848

Chemical Taxonomy

Classification

Not classified

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	2.5	ALOGPS
logP	2.32	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	141.4 m³·mol⁻¹	ChemAxon
Polarizability	51.69 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014059

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135530281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsumoto M, Minato H, Kondo E, Mitsugi T, Katagiri K: Cephalochromin, dihydroisoustilaginoidin A, and iso-ustilaginoidin A from Verticillium sp. K-113. J Antibiot (Tokyo). 1975 Aug;28(8):602-4. doi: 10.7164/antibiotics.28.602. [PubMed:1171848 ]

Showing NP-Card for Dihydroisoustilaginoidin A (NP0003946)

MOL for NP0003946 (Dihydroisoustilaginoidin A)

3D MOL for NP0003946 (Dihydroisoustilaginoidin A)

3D SDF for NP0003946 (Dihydroisoustilaginoidin A)

3D-SDF for NP0003946 (Dihydroisoustilaginoidin A)

PDB for NP0003946 (Dihydroisoustilaginoidin A)

3D PDB for NP0003946 (Dihydroisoustilaginoidin A)

SMILES for NP0003946 (Dihydroisoustilaginoidin A)

INCHI for NP0003946 (Dihydroisoustilaginoidin A)

Structure for NP0003946 (Dihydroisoustilaginoidin A)

3D Structure for NP0003946 (Dihydroisoustilaginoidin A)