NP-MRD: Showing NP-Card for Purpactin A (NP0008983)

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Record Information

Version

1.0

Created at

2020-12-09 06:27:24 UTC

Updated at

2021-07-15 17:01:58 UTC

NP-MRD ID

NP0008983

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpactin A

Provided By

NPAtlas

Description

AS-186b, also known as purpactin a or vermixocin b, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. AS-186b is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Purpactin A is found in Penicillium, Penicillium asperosporum, Talaromyces purpureogenus, Penicillium simplicissimum, Pseudopenicillium megasporum and Talaromyces flavus. It was first documented in 1991 (PMID: 2010354). Based on a literature review a small amount of articles have been published on AS-186b (PMID: 8119857) (PMID: 17390588) (PMID: 1750931) (PMID: 2010355).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106313D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242106313D          

 56 58  0  0  0  0            999 V2000
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   -2.9865   -0.7079    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3996   -2.4823    0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -1.6542   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512   -1.4201    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4572   -0.1413   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135    0.4579   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8098    0.7911    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7964   -2.3114   -0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6206   -1.9274   -2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -3.3044   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    3.1929    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555    3.4537    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    3.5789    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.0455    2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -2.2562    2.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416    1.8040   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6179    2.4401   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9744    1.5744   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1880    0.9673   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4525    0.8353    0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.6241   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -1.7557    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -2.6748    1.9343 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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  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
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 17  3  1  0  0  0  0
 29 22  1  0  0  0  0
 30 16  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  5 34  1  1  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  7 37  1  1  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 14 47  1  0  0  0  0
 15 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 23 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  0  0  0  0
 28 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008983

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC3=C(C(OC([H])([H])[H])=C(C([H])=C3[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C(=O)OC([H])([H])C2=C([H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O7/c1-12(2)8-19(29-14(4)24)16-6-7-18-20(22(16)27-5)23(26)28-11-15-9-13(3)10-17(25)21(15)30-18/h6-7,9-10,12,19,25H,8,11H2,1-5H3/t19-/m0/s1

> <INCHI_KEY>
NUYFKDBCHFKOBT-IBGZPJMESA-N

> <FORMULA>
C23H26O7

> <MOLECULAR_WEIGHT>
414.454

> <EXACT_MASS>
414.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.0541222324385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-{16-hydroxy-7-methoxy-14-methyl-9-oxo-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3(8),4,6,12,14-hexaen-6-yl}-3-methylbutyl acetate

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.424882890333333

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.222368314253387

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.395531208968766

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7534326129522833

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
110.42379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-{16-hydroxy-7-methoxy-14-methyl-9-oxo-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3(8),4,6,12,14-hexaen-6-yl}-3-methylbutyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -1.4619    2.0652   -1.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    0.7217   -1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -0.0552   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -0.7563    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -0.4705    0.5639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5956   -1.4977   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -1.2844   -0.1009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5290    0.0394   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287   -2.3438   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    0.8545    0.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5501    1.5895    1.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8590    3.0432    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168    1.0213    2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449   -1.5179    1.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -1.6542    1.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.9584    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7964   -0.1895   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245    0.5235   -1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.4746   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4805    1.1960   -1.8137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.5207   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482    0.4510   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.7126   -0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6559   -0.0717    0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126    0.2431   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3117   -1.1519    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829   -1.4149    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -2.4702    1.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.6348    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024   -1.2234    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572    2.6563   -2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    2.1423   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    2.6491   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -0.7079    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3996   -2.4823    0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -1.6542   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512   -1.4201    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4572   -0.1413   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135    0.4579   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8098    0.7911    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7964   -2.3114   -0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6206   -1.9274   -2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -3.3044   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    3.1929    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555    3.4537    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    3.5789    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.0455    2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -2.2562    2.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416    1.8040   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6179    2.4401   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9744    1.5744   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1880    0.9673   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4525    0.8353    0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.6241   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -1.7557    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -2.6748    1.9343 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
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 17  3  1  0
 29 22  1  0
 30 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  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      -1.462   2.065  -1.449  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.105   0.722  -1.405  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.563  -0.055  -0.437  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.299  -0.756   0.517  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.766  -0.471   0.564  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.596  -1.498  -0.108  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.064  -1.284  -0.101  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.529   0.039  -0.701  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.729  -2.344  -1.052  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.067   0.855   0.441  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.550   1.589   1.533  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.859   3.043   1.416  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.717   1.021   2.605  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.645  -1.518   1.440  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.730  -1.654   1.515  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.478  -0.958   0.569  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.796  -0.190  -0.371  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.325   0.524  -1.541  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.476   0.475  -2.479  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.481   1.196  -1.814  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.702   1.521  -1.219  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.348   0.451  -0.420  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.713   0.713  -0.599  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.656  -0.072   0.003  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.113   0.243  -0.227  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.312  -1.152   0.812  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.983  -1.415   0.994  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.572  -2.470   1.789  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.013  -0.635   0.393  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.802  -1.223   0.821  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.957   2.656  -2.277  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.555   2.142  -1.791  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.277   2.649  -0.550  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.986  -0.708   1.697  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.400  -2.482   0.395  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.295  -1.654  -1.189  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.551  -1.420   0.863  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.457  -0.141  -1.273  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.814   0.458  -1.435  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.810   0.791   0.073  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.796  -2.311  -0.816  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.621  -1.927  -2.097  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.230  -3.304  -0.956  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.886   3.193   1.021  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.756   3.454   2.454  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.183   3.579   0.716  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.254  -2.046   2.176  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.216  -2.256   2.257  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.442   1.804  -2.026  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.618   2.440  -0.571  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.974   1.574  -1.255  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.188   0.967  -1.081  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.453   0.835   0.662  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.714  -0.624  -0.464  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.081  -1.756   1.272  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.591  -2.675   1.934  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10   34                                             
CONECT    6    5    7   35   36                                             
CONECT    7    6    8    9   37                                             
CONECT    8    7   38   39   40                                             
CONECT    9    7   41   42   43                                             
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   44   45   46                                             
CONECT   13   11                                                            
CONECT   14    4   15   47                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18    3                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   49   50                                             
CONECT   22   21   23   29                                                  
CONECT   23   22   24   51                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   52   53   54                                             
CONECT   26   24   27   55                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   56                                                       
CONECT   29   27   30   22                                                  
CONECT   30   29   16                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -1.4619    2.0652   -1.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    0.7217   -1.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -0.0552   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -0.7563    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -0.4705    0.5639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5956   -1.4977   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -1.2844   -0.1009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5290    0.0394   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287   -2.3438   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    0.8545    0.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5501    1.5895    1.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8590    3.0432    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168    1.0213    2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3482    0.4510   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.7126   -0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6559   -0.0717    0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126    0.2431   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3117   -1.1519    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829   -1.4149    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5719   -2.4702    1.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.6348    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024   -1.2234    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572    2.6563   -2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    2.1423   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767    2.6491   -0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -0.7079    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3996   -2.4823    0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -1.6542   -1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512   -1.4201    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4572   -0.1413   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135    0.4579   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8098    0.7911    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7964   -2.3114   -0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6206   -1.9274   -2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304   -3.3044   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857    3.1929    1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555    3.4537    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833    3.5789    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.0455    2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2163   -2.2562    2.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416    1.8040   -2.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6179    2.4401   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9744    1.5744   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1880    0.9673   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4525    0.8353    0.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -0.6241   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -1.7557    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -2.6748    1.9343 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
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 17  3  1  0
 29 22  1  0
 30 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1'-O-Acetylpenicillide	ChEBI
Purpactin a	ChEBI
Vermixocin b	ChEBI
AS 186b	MeSH
3-1'-Acetoxy-11-hydroxy-4-methoxy-9-methyl-3'-methylbutyl-5H,7H-dibenzo(b,g)-1,5-dioxocin-5-one	MeSH
3-(1'-Acetoxy-3'-methylbutyl)-11-hydroxy-4-methoxy-9-methyl-5H,7H-dibenzo(c,F)(1,5)-dioxocin-5-one	MeSH

Chemical Formula

C₂₃H₂₆O₇

Average Mass

414.4540 Da

Monoisotopic Mass

414.16785 Da

IUPAC Name

(1S)-1-{16-hydroxy-7-methoxy-14-methyl-9-oxo-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3(8),4,6,12,14-hexaen-6-yl}-3-methylbutyl acetate

Traditional Name

(1S)-1-{16-hydroxy-7-methoxy-14-methyl-9-oxo-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3(8),4,6,12,14-hexaen-6-yl}-3-methylbutyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(C=CC2=C1C(=O)OCC1=CC(C)=CC(O)=C1O2)[C@H](CC(C)C)OC(C)=O

InChI Identifier

InChI=1S/C23H26O7/c1-12(2)8-19(29-14(4)24)16-6-7-18-20(22(16)27-5)23(26)28-11-15-9-13(3)10-17(25)21(15)30-18/h6-7,9-10,12,19,25H,8,11H2,1-5H3/t19-/m0/s1

InChI Key

NUYFKDBCHFKOBT-IBGZPJMESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	2010354
Penicillium asperosporum	LOTUS Database	35616633
Penicillium purpurogenum	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633
Pseudopenicillium megasporum	LOTUS Database	35616633
Talaromyces flavus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium purpurogenum FO-608	KNApSAcK Database	22123792
Penicillium simplicissimum IFM53375	KNApSAcK Database	22123792
Penicillium vermiculatum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:65444 )
phenols (CHEBI:65444 )
acetate ester (CHEBI:65444 )
lactone (CHEBI:65444 )
dibenzodioxocine (CHEBI:65444 )

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	4.32	ALOGPS
logP	4.42	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.42 m³·mol⁻¹	ChemAxon
Polarizability	45.05 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	Yes	ChemAxon

External Links

NPAtlas ID

NPA005415

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016738

Chemspider ID

8517181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10341722

PDB ID

Not Available

ChEBI ID

65444

Good Scents ID

Not Available

References

General References

Nishida H, Tomoda H, Cao J, Okuda S, Omura S: Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. II. Structure elucidation of purpactins A, B and C. J Antibiot (Tokyo). 1991 Feb;44(2):144-51. doi: 10.7164/antibiotics.44.144. [PubMed:2010354 ]
Kuroda K, Morishita Y, Saito Y, Ikuina Y, Ando K, Kawamoto I, Matsuda Y: AS-186 compounds, new inhibitors of acyl-CoA: cholesterol acyltransferase from Penicillium asperosporum KY1635. J Antibiot (Tokyo). 1994 Jan;47(1):16-22. doi: 10.7164/antibiotics.47.16. [PubMed:8119857 ]
Ohshiro T, Rudel LL, Omura S, Tomoda H: Selectivity of microbial acyl-CoA: cholesterol acyltransferase inhibitors toward isozymes. J Antibiot (Tokyo). 2007 Jan;60(1):43-51. doi: 10.1038/ja.2007.6. [PubMed:17390588 ]
Tomoda H, Nishida H, Masuma R, Cao J, Okuda S, Omura S: Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. I. Production, isolation and physico-chemical and biological properties. J Antibiot (Tokyo). 1991 Feb;44(2):136-43. doi: 10.7164/antibiotics.44.136. [PubMed:1750931 ]
Nishida H, Tomoda H, Cao J, Araki S, Okuda S, Omura S: Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. III. Chemical modification of purpactin A. J Antibiot (Tokyo). 1991 Feb;44(2):152-9. doi: 10.7164/antibiotics.44.152. [PubMed:2010355 ]

Showing NP-Card for Purpactin A (NP0008983)

MOL for NP0008983 (Purpactin A)

3D MOL for NP0008983 (Purpactin A)

3D SDF for NP0008983 (Purpactin A)

3D-SDF for NP0008983 (Purpactin A)

PDB for NP0008983 (Purpactin A)

3D PDB for NP0008983 (Purpactin A)

SMILES for NP0008983 (Purpactin A)

INCHI for NP0008983 (Purpactin A)

Structure for NP0008983 (Purpactin A)

3D Structure for NP0008983 (Purpactin A)