NP-MRD: Showing NP-Card for Asperanthone (NP0018802)

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Record Information

Version

2.0

Created at

2021-01-06 04:23:59 UTC

Updated at

2021-07-15 17:29:12 UTC

NP-MRD ID

NP0018802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperanthone

Provided By

NPAtlas

Description

Asperanthone belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Asperanthone is found in Aspergillus. Asperanthone was first documented in 2018 (PMID: 30294975). Based on a literature review very few articles have been published on Asperanthone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104383D          

 62 65  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242104383D          

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    8.0900   -0.0111   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0265   -1.0773   -1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603   -1.5217    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215   -0.2698    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.2069   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952   -1.2445   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0590   -3.3598   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -4.8206   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -4.0033   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5021    2.6142   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8843    2.4727    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0379   -2.4456    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  3  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 23  7  1  0  0  0  0
 23 12  2  0  0  0  0
 21 15  1  0  0  0  0
 30 16  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4 40  1  1  0  0  0
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  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
  8 44  1  0  0  0  0
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 29 57  1  0  0  0  0
 29 58  1  0  0  0  0
 30 59  1  6  0  0  0
 33 60  1  0  0  0  0
 33 61  1  0  0  0  0
 33 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0018802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C2=C1C(=O)C1=C3C(OC([H])([H])[C@@]([H])(C(=C([H])[H])C([H])([H])[H])[C@]3([H])OC(=O)C([H])([H])[H])=C(C([H])=C1O2)C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C(=C([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O7/c1-12(2)17-11-32-25-14(5)9-20-22(23(25)27(17)33-15(6)28)24(31)21-18(29)8-7-16(26(21)34-20)10-19(30)13(3)4/h7-9,17,19,27,29-30H,1,3,10-11H2,2,4-6H3/t17-,19-,27-/m0/s1

> <INCHI_KEY>
VPPUNOXCKFHURD-PNGUEYMGSA-N

> <FORMULA>
C27H28O7

> <MOLECULAR_WEIGHT>
464.514

> <EXACT_MASS>
464.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.96425858116445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-6-hydroxy-9-[(2S)-2-hydroxy-3-methylbut-3-en-1-yl]-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.702757643333333

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.508267458344747

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.669015871443076

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0326269460370074

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
126.86489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-6-hydroxy-9-[(2S)-2-hydroxy-3-methylbut-3-en-1-yl]-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    5.9668    1.4770    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    0.3296   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0936   -3.0008   -1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712   -3.7705   -1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -3.2798   -1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223   -4.1079   -1.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.9581   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -1.3283   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6002    0.7123   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    0.1449   -0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -1.1163   -1.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0276   -0.2466    0.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2206   -0.8197    1.6416 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1627   -2.7264    0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0937    1.7853    1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0900   -0.0111   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0590   -3.3598   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -4.8206   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -4.0033   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    4.2302    1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995    4.7066   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    4.3962    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3105   -0.8841   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138   -3.7211    3.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714   -2.1137    3.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -2.4456    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  3
 27 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 23  7  1  0
 23 12  2  0
 21 15  1  0
 30 16  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  1
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  6
 33 60  1  0
 33 61  1  0
 33 62  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       5.967   1.477   0.427  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.963   0.330  -0.218  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.134  -0.072  -1.019  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.781  -0.554  -0.135  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.861  -0.083   0.779  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.179  -0.795  -1.520  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.989  -1.677  -1.462  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.094  -3.001  -1.823  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.971  -3.771  -1.744  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.726  -3.280  -1.317  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.322  -4.108  -1.272  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.669  -1.958  -0.969  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.501  -1.328  -0.527  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.507  -2.030  -0.457  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.568  -0.001  -0.176  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.787   0.527   0.254  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.768   1.889   0.596  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.586   2.611   0.491  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.622   4.070   0.869  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.585   2.047   0.063  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.600   0.712  -0.279  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.722   0.145  -0.694  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.782  -1.116  -1.027  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.891   2.570   1.044  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.030   1.795   1.393  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.193   0.791   0.302  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.311   1.331  -1.050  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.547   0.986  -2.067  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.384   2.350  -1.287  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.028  -0.247   0.352  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.221  -0.820   1.642  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.780  -2.041   1.833  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.973  -2.641   3.208  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.163  -2.726   0.852  0.00  0.00           O+0
HETATM   35  H   UNK     0       6.827   2.126   0.370  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.094   1.785   1.029  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.285   0.679  -1.848  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.090  -0.011  -0.424  0.00  0.00           H+0
HETATM   39  H   UNK     0       7.027  -1.077  -1.468  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.160  -1.522   0.290  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.122  -0.270   1.704  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.935   0.207  -1.929  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.995  -1.244  -2.131  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.059  -3.360  -2.148  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.053  -4.821  -2.030  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.237  -4.003  -1.023  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.473   4.230   1.559  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.800   4.707  -0.026  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.353   4.396   1.289  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.502   2.614  -0.016  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.884   2.473   1.378  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.922   1.261   2.351  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.102   0.156   0.495  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.706   1.444  -3.052  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.742   0.268  -2.041  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.154   2.337  -0.477  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.862   2.060  -2.257  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.927   3.346  -1.426  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.311  -0.884  -0.480  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.814  -3.721   3.165  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.371  -2.114   3.958  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.038  -2.446   3.452  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   37   38   39                                             
CONECT    4    2    5    6   40                                             
CONECT    5    4   41                                                       
CONECT    6    4    7   42   43                                             
CONECT    7    6    8   23                                                  
CONECT    8    7    9   44                                                  
CONECT    9    8   10   45                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   46                                                       
CONECT   12   10   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   47   48   49                                             
CONECT   20   18   21   50                                                  
CONECT   21   20   22   15                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   12                                                  
CONECT   24   17   25                                                       
CONECT   25   24   26   51   52                                             
CONECT   26   25   27   30   53                                             
CONECT   27   26   28   29                                                  
CONECT   28   27   54   55                                                  
CONECT   29   27   56   57   58                                             
CONECT   30   26   31   16   59                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   60   61   62                                             
CONECT   34   32                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   11                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   30                                                            
CONECT   60   33                                                            
CONECT   61   33                                                            
CONECT   62   33                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    5.9668    1.4770    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    0.3296   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1338   -0.0723   -1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7806   -0.5543   -0.1351 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8615   -0.0833    0.7787 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790   -0.7952   -1.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -1.6770   -1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0936   -3.0008   -1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712   -3.7705   -1.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -3.2798   -1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223   -4.1079   -1.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.9581   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -1.3283   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074   -2.0296   -0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -0.0008   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    0.5270    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7677    1.8889    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5864    2.6109    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216    4.0704    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    2.0472    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6002    0.7123   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216    0.1449   -0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -1.1163   -1.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8913    2.5695    1.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0297    1.7949    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    0.7913    0.3023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3113    1.3309   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5473    0.9864   -2.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3836    2.3503   -1.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276   -0.2466    0.3520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2206   -0.8197    1.6416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7796   -2.0405    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -2.6407    3.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1627   -2.7264    0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275    2.1259    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937    1.7853    1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2853    0.6791   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0900   -0.0111   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0265   -1.0773   -1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603   -1.5217    0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215   -0.2698    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.2069   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952   -1.2445   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0590   -3.3598   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -4.8206   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373   -4.0033   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    4.2302    1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7995    4.7066   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    4.3962    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    2.6142   -0.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8843    2.4727    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9216    1.2611    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1018    0.1559    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7064    1.4438   -3.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422    0.2683   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1543    2.3371   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8617    2.0603   -2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269    3.3461   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -0.8841   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138   -3.7211    3.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714   -2.1137    3.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -2.4456    3.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  3
 27 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 23  7  1  0
 23 12  2  0
 21 15  1  0
 30 16  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  1
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 29 58  1  0
 30 59  1  6
 33 60  1  0
 33 61  1  0
 33 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₇

Average Mass

464.5140 Da

Monoisotopic Mass

464.18350 Da

IUPAC Name

(3R,4S)-6-hydroxy-9-[(2S)-2-hydroxy-3-methylbut-3-en-1-yl]-12-methyl-5-oxo-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-4-yl acetate

Traditional Name

(3R,4S)-6-hydroxy-9-[(2S)-2-hydroxy-3-methylbut-3-en-1-yl]-12-methyl-5-oxo-3-(prop-1-en-2-yl)-3,4-dihydro-2H-1,10-dioxatetraphen-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](COC2=C1C1=C(OC3=C(CC(O)C(C)=C)C=CC(O)=C3C1=O)C=C2C)C(C)=C

InChI Identifier

InChI=1S/C27H28O7/c1-12(2)17-11-32-25-14(5)9-20-22(23(25)27(17)33-15(6)28)24(31)21-18(29)8-7-16(26(21)34-20)10-19(30)13(3)4/h7-9,17,19,27,29-30H,1,3,10-11H2,2,4-6H3/t17-,19?,27-/m0/s1

InChI Key

VPPUNOXCKFHURD-PNGUEYMGSA-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
Aspergillus	NPAtlas	30294975

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Pyranoxanthone
Chromone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	3.5	ALOGPS
logP	4.7	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.86 m³·mol⁻¹	ChemAxon
Polarizability	49.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA027832

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

146684064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qiao Y, Tu K, Feng W, Liu J, Xu Q, Tao L, Zhu H, Chen C, Wang J, Xue Y, Zhang Y: Polyketide and Prenylxanthone Derivatives from the Endophytic Fungus Aspergillus sp. TJ23. Chem Biodivers. 2018 Dec;15(12):e1800395. doi: 10.1002/cbdv.201800395. Epub 2018 Dec 7. [PubMed:30294975 ]

Showing NP-Card for Asperanthone (NP0018802)

MOL for NP0018802 (Asperanthone)

3D MOL for NP0018802 (Asperanthone)

3D SDF for NP0018802 (Asperanthone)

3D-SDF for NP0018802 (Asperanthone)

PDB for NP0018802 (Asperanthone)

3D PDB for NP0018802 (Asperanthone)

SMILES for NP0018802 (Asperanthone)

INCHI for NP0018802 (Asperanthone)

Structure for NP0018802 (Asperanthone)

3D Structure for NP0018802 (Asperanthone)