NP-MRD: Showing NP-Card for Aspergiolide D (NP0009719)

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Record Information

Version

2.0

Created at

2021-01-05 19:17:56 UTC

Updated at

2021-07-15 17:04:03 UTC

NP-MRD ID

NP0009719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergiolide D

Provided By

NPAtlas

Description

Aspergiolide D is found in Aspergillus glaucus. Based on a literature review very few articles have been published on 4',6,8,14'-tetrahydroxy-2'-methoxy-3,12'-dimethyl-1H-10'-oxaspiro[naphthalene-2,6'-pentacyclo[13.3.1.0⁵,¹⁸.0⁸,¹⁷.0¹¹,¹⁶]Nonadecane]-1',3',5'(18'),8'(17'),11'(16'),12',14'-heptaene-1,7',9',19'-tetrone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106523D          

 58 64  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242106523D          

 58 64  0  0  0  0            999 V2000
   -1.7032    5.2434   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281    3.9643   -0.7670 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6989   -0.3431    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -0.1186    1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    0.1956    3.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.2253    1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045   -0.5408    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.6359   -0.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238   -0.7637   -0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1753   -0.6651   -0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120   -0.9002   -1.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9248   -0.8332   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -1.1025   -2.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660    5.5573   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1133   -3.4485    2.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6613   -1.1485   -2.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5850   -0.6912   -3.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373   -0.7272   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205   -2.2023   -2.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 18 19  1  0  0  0  0
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 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
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 36 37  2  0  0  0  0
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  9  3  1  0  0  0  0
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 27  7  1  0  0  0  0
 37 30  1  0  0  0  0
 23  8  1  0  0  0  0
 24 18  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  4 44  1  0  0  0  0
  6 45  1  0  0  0  0
 14 46  1  0  0  0  0
 15 47  1  0  0  0  0
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 17 50  1  0  0  0  0
 32 51  1  0  0  0  0
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 35 53  1  0  0  0  0
 36 54  1  0  0  0  0
 38 55  1  0  0  0  0
 40 56  1  0  0  0  0
 40 57  1  0  0  0  0
 40 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)[C@]3(C(=O)C4=C5C6=C(C(O[H])=C([H])C(=C6OC4=O)C([H])([H])[H])C(=O)C4=C5C3=C(O[H])C([H])=C4OC([H])([H])[H])C(=C([H])C2=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O10/c1-9-4-13(32)18-22-20-21-19(25(18)35)16(39-3)8-15(34)24(21)30(28(37)23(20)29(38)40-26(9)22)10(2)5-11-6-12(31)7-14(33)17(11)27(30)36/h4-8,31-34H,1-3H3/t30-/m0/s1

> <INCHI_KEY>
NWYKACHSINRRPF-UHFFFAOYSA-N

> <FORMULA>
C30H18O10

> <MOLECULAR_WEIGHT>
538.464

> <EXACT_MASS>
538.08999678

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
53.86175116672204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4',6,8,14'-tetrahydroxy-2'-methoxy-3,12'-dimethyl-1H-10'-oxaspiro[naphthalene-2,6'-pentacyclo[13.3.1.0^{5,18}.0^{8,17}.0^{11,16}]nonadecane]-1'(18'),2',4',8'(17'),11',13',15'-heptaene-1,7',9',19'-tetrone

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.980884196

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.788929293401729

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.128158642434429

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889542273449812

> <JCHEM_POLAR_SURFACE_AREA>
167.65999999999997

> <JCHEM_REFRACTIVITY>
150.5835

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4',6,8,14'-tetrahydroxy-2'-methoxy-3,12'-dimethyl-10'-oxaspiro[naphthalene-2,6'-pentacyclo[13.3.1.0^{5,18}.0^{8,17}.0^{11,16}]nonadecane]-1'(18'),2',4',8'(17'),11',13',15'-heptaene-1,7',9',19'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
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    1.3278   -2.8289    0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7866   -0.6359   -0.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1753   -0.6651   -0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120   -0.9002   -1.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9248   -0.8332   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -1.1025   -2.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660    5.5573   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5243    5.2924   -2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5465   -4.2056    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6673   -0.0452    2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -0.4739    0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0373   -0.7272   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205   -2.2023   -2.7736 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
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  8  9  2  0
  9 10  1  0
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 19 20  1  0
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 20 22  1  0
 22 23  2  0
 23 24  1  0
 22 25  1  0
 25 26  2  0
 27 25  1  1
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
  9  3  1  0
 24 12  2  0
 39 27  1  0
 27  7  1  0
 37 30  1  0
 23  8  1  0
 24 18  1  0
  1 41  1  0
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  1 43  1  0
  4 44  1  0
  6 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
 32 51  1  0
 33 52  1  0
 35 53  1  0
 36 54  1  0
 38 55  1  0
 40 56  1  0
 40 57  1  0
 40 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      -1.703   5.243  -1.125  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.128   3.964  -0.767  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.282   2.886  -0.623  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.073   2.955  -0.817  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.877   1.875  -0.667  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.260   1.916  -0.857  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.354   0.620  -0.302  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.985   0.526  -0.104  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.815   1.653  -0.262  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.246   1.522  -0.044  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.932   2.568  -0.201  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.833   0.254   0.332  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.167   0.105   0.542  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.059   1.115   0.420  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.655  -1.170   0.906  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.787  -2.213   1.039  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.377  -3.540   1.430  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.431  -2.093   0.834  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.657  -3.123   0.976  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.361  -3.085   0.798  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.611  -4.069   0.932  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.815  -1.833   0.431  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.611  -0.736   0.276  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.971  -0.841   0.478  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.600  -1.762   0.231  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.328  -2.829   0.392  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.293  -0.509  -0.159  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.279  -0.267   0.895  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.847   0.041   2.074  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.699  -0.343   0.730  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.607  -0.119   1.749  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.215   0.196   3.006  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.976  -0.225   1.450  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.404  -0.541   0.192  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.787  -0.636  -0.059  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.524  -0.764  -0.818  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.175  -0.665  -0.549  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.212  -0.900  -1.614  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.925  -0.833  -1.455  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.051  -1.103  -2.663  0.00  0.00           C+0
HETATM   41  H   UNK     0      -0.766   5.557  -0.622  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.524   5.292  -2.234  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.466   5.989  -0.875  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.484   3.915  -1.097  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.655   2.827  -1.124  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.970   2.047   0.188  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.734  -1.280   1.073  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.792  -3.962   0.485  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.547  -4.206   1.767  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.113  -3.449   2.232  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.408   0.327   3.468  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.667  -0.045   2.264  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.440  -0.474   0.676  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.897  -1.012  -1.806  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.661  -1.149  -2.602  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.585  -0.691  -3.531  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.037  -0.727  -2.515  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.020  -2.202  -2.774  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   44                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   45                                                       
CONECT    7    5    8   27                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   46                                                       
CONECT   15   13   16   47                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   48   49   50                                             
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24    8                                                  
CONECT   24   23   12   18                                                  
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   39    7                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   37                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   51                                                       
CONECT   33   31   34   52                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   53                                                       
CONECT   36   34   37   54                                                  
CONECT   37   36   38   30                                                  
CONECT   38   37   39   55                                                  
CONECT   39   38   40   27                                                  
CONECT   40   39   56   57   58                                             
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    4                                                            
CONECT   45    6                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   32                                                            
CONECT   52   33                                                            
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   38                                                            
CONECT   56   40                                                            
CONECT   57   40                                                            
CONECT   58   40                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

RDKit          3D

58 64  0  0  0  0  0  0  0  0999 V2000
   -1.7032    5.2434   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281    3.9643   -0.7670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    2.8856   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0725    2.9549   -0.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766    1.8750   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596    1.9164   -0.8573 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    0.6196   -0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9854    0.5259   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    1.6531   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464    1.5216   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9316    2.5679   -0.2014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333    0.2535    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1673    0.1052    0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0589    1.1145    0.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6548   -1.1699    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6566   -3.1226    0.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6105   -4.0686    0.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8150   -1.8326    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111   -0.7357    0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9713   -0.8412    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -1.7617    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3278   -2.8289    0.3920 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2928   -0.5089   -0.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2792   -0.2671    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8466    0.0408    2.0743 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989   -0.3431    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071   -0.1186    1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    0.1956    3.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.2253    1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045   -0.5408    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.6359   -0.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5238   -0.7637   -0.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1753   -0.6651   -0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120   -0.9002   -1.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9248   -0.8332   -1.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -1.1025   -2.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660    5.5573   -0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5243    5.2924   -2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4659    5.9892   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835    3.9150   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6553    2.8274   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9701    2.0472    0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7342   -1.2799    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7923   -3.9625    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5465   -4.2056    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133   -3.4485    2.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079    0.3272    3.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6673   -0.0452    2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -0.4739    0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8971   -1.0124   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -1.1485   -2.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5850   -0.6912   -3.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0373   -0.7272   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205   -2.2023   -2.7736 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
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 22 25  1  0
 25 26  2  0
 27 25  1  1
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
  9  3  1  0
 24 12  2  0
 39 27  1  0
 27  7  1  0
 37 30  1  0
 23  8  1  0
 24 18  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  4 44  1  0
  6 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
 32 51  1  0
 33 52  1  0
 35 53  1  0
 36 54  1  0
 38 55  1  0
 40 56  1  0
 40 57  1  0
 40 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₀H₁₈O₁₀

Average Mass

538.4640 Da

Monoisotopic Mass

538.09000 Da

IUPAC Name

(2S)-4',6,8,14'-tetrahydroxy-2'-methoxy-3,12'-dimethyl-1H-10'-oxaspiro[naphthalene-2,6'-pentacyclo[13.3.1.0^{5,18}.0^{8,17}.0^{11,16}]nonadecane]-1'(18'),2',4',8'(17'),11',13',15'-heptaene-1,7',9',19'-tetrone

Traditional Name

(2S)-4',6,8,14'-tetrahydroxy-2'-methoxy-3,12'-dimethyl-10'-oxaspiro[naphthalene-2,6'-pentacyclo[13.3.1.0^{5,18}.0^{8,17}.0^{11,16}]nonadecane]-1'(18'),2',4',8'(17'),11',13',15'-heptaene-1,7',9',19'-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C3=C1C(=O)C1=C(O)C=C(C)C4=C1C3=C(C(=O)O4)C(=O)C21C(C)=CC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C30H18O10/c1-9-4-13(32)18-22-20-21-19(25(18)35)16(39-3)8-15(34)24(21)30(28(37)23(20)29(38)40-26(9)22)10(2)5-11-6-12(31)7-14(33)17(11)27(30)36/h4-8,31-34H,1-3H3

InChI Key

NWYKACHSINRRPF-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
Aspergillus glaucus	NPAtlas	21243700

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Anthracene
Naphthopyran
Phenanthrene
Coumarin
2-naphthol
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	3.89	ALOGPS
logP	4.98	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	150.58 m³·mol⁻¹	ChemAxon
Polarizability	53.86 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016092

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435030

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52952452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aspergiolide D (NP0009719)

MOL for NP0009719 (Aspergiolide D)

3D MOL for NP0009719 (Aspergiolide D)

3D SDF for NP0009719 (Aspergiolide D)

3D-SDF for NP0009719 (Aspergiolide D)

PDB for NP0009719 (Aspergiolide D)

3D PDB for NP0009719 (Aspergiolide D)

SMILES for NP0009719 (Aspergiolide D)

INCHI for NP0009719 (Aspergiolide D)

Structure for NP0009719 (Aspergiolide D)

3D Structure for NP0009719 (Aspergiolide D)