NP-MRD: Showing NP-Card for verrucosidin (NP0028161)

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Record Information

Version

2.0

Created at

2021-06-19 20:07:22 UTC

Updated at

2021-06-29 23:54:45 UTC

NP-MRD ID

NP0028161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

verrucosidin

Provided By

JEOL Database JEOL Logo

Description

verrucosidin is found in Penicillium sp., Penicillium verrucosum and Talaromyces verruculosus. verrucosidin was first documented in 2012 (PMID: 22119450). Based on a literature review a significant number of articles have been published on Verrucosidin (PMID: 24773150) (PMID: 26243556) (PMID: 26954888) (PMID: 27548192) (PMID: 34093475) (PMID: 33016118).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122073D          

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     RDKit          3D

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M  END


  Mrv1652306192122073D          

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   -3.8421    3.0681    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27 26  1  0  0  0  0
 11 13  2  0  0  0  0
 20 22  1  0  0  0  0
 11 12  1  0  0  0  0
 26  6  1  0  0  0  0
 13 14  1  0  0  0  0
 22 25  1  0  0  0  0
 14 16  2  0  0  0  0
  6  4  2  0  0  0  0
 14 15  1  0  0  0  0
 17 16  1  1  0  0  0
 25 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  3 29  2  0  0  0  0
  2  1  1  0  0  0  0
 17 19  1  0  0  0  0
 29 30  1  0  0  0  0
 27 28  2  0  0  0  0
 20 21  1  0  0  0  0
  7  8  1  1  0  0  0
 22 23  1  6  0  0  0
 29 27  1  0  0  0  0
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  7  9  1  0  0  0  0
 10  9  1  0  0  0  0
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 18 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(\C(=C(/[H])[C@@]1(O[C@]([H])(C([H])([H])[H])[C@]2(O[C@@]12[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])=C(\C([H])([H])[H])[C@]1([H])O[C@]1(C1=C(C(OC([H])([H])[H])=C(C(=O)O1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3/b12-11+,13-10+/t16-,18+,21+,22+,23-,24-/m1/s1

> <INCHI_KEY>
JSVLNARHSWZARV-FOOXNAEUSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.71119012965818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-3,5-dimethyl-6-[(2R,3S)-2-methyl-3-[(2E,4E)-4-methyl-5-[(1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]penta-2,4-dien-2-yl]oxiran-2-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.38680576

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7595583304774327

> <JCHEM_POLAR_SURFACE_AREA>
69.82

> <JCHEM_REFRACTIVITY>
115.5577

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-3,5-dimethyl-6-[(2R,3S)-2-methyl-3-[(2E,4E)-4-methyl-5-[(1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]penta-2,4-dien-2-yl]oxiran-2-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    6.4564   -1.4849   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11 13  2  0
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 18 49  1  0
 18 50  1  0
 18 51  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       6.093  -3.838   1.679  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.864  -2.520   2.184  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.851  -1.886   1.491  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.537  -1.926   2.112  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.412  -2.607   3.450  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.504  -1.332   1.480  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.100  -1.293   1.961  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.731  -0.115   2.824  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.368  -2.478   2.322  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.068  -1.942   1.027  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.190  -1.228   0.707  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.042  -0.155  -0.345  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.368  -1.564   1.275  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.669  -0.946   1.058  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.739  -1.906   0.616  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.857   0.361   1.337  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.094   1.231   1.184  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.858   1.255   2.510  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.974   0.683   0.173  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.941   1.507  -1.017  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.232   0.726  -2.112  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.266   2.784  -0.644  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.612   3.665  -1.643  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.882   3.493   0.447  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.767   2.632   0.735  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.723  -0.654   0.248  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.955  -0.529  -0.319  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.116   0.091  -1.365  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.086  -1.186   0.370  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.430  -1.002  -0.266  0.00  0.00           C+0
HETATM   31  H   UNK     0       5.186  -4.449   1.729  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.467  -3.807   0.650  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.858  -4.309   2.304  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.437  -2.451   3.920  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.556  -3.687   3.349  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.157  -2.218   4.154  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.409  -0.039   3.681  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.800   0.816   2.253  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.286  -0.195   3.223  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.436  -2.529   0.189  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.401  -0.509  -1.160  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.993   0.134  -0.800  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.582   0.739   0.087  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.380  -2.397   1.979  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.589  -2.898   1.057  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.739  -1.593   0.927  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.724  -2.016  -0.473  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.003   0.906   1.741  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.792   1.821   2.414  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.266   1.713   3.310  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.144   0.244   2.822  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.978   1.692  -1.315  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.190   0.523  -1.846  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.241   1.271  -3.061  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.716  -0.244  -2.265  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.740   3.173  -2.085  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.269   4.603  -1.193  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.311   3.917  -2.447  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.842   3.068   1.071  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.242  -1.424   0.335  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.650   0.063  -0.396  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.456  -1.485  -1.248  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   29                                                  
CONECT    4    6    5    3                                                  
CONECT    5    4   34   35   36                                             
CONECT    6   26    4    7                                                  
CONECT    7    8   10    9    6                                             
CONECT    8    7   37   38   39                                             
CONECT    9    7   10                                                       
CONECT   10    7   40   11    9                                             
CONECT   11   13   12   10                                                  
CONECT   12   11   41   42   43                                             
CONECT   13   11   14   44                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   45   46   47                                             
CONECT   16   14   17   48                                                  
CONECT   17   16   25   19   18                                             
CONECT   18   17   49   50   51                                             
CONECT   19   17   20                                                       
CONECT   20   22   21   19   52                                             
CONECT   21   20   53   54   55                                             
CONECT   22   20   25   23   24                                             
CONECT   23   22   56   57   58                                             
CONECT   24   25   22                                                       
CONECT   25   22   17   24   59                                             
CONECT   26   27    6                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29    3   30   27                                                  
CONECT   30   29   60   61   62                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   23                                                            
CONECT   59   25                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
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
    6.0935   -3.8381    1.6788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645   -2.5204    2.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508   -1.8858    1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -1.9257    2.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4116   -2.6067    3.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044   -1.3322    1.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0997   -1.2933    1.9613 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7309   -0.1152    2.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3684   -2.4783    2.3221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -1.9422    1.0271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1904   -1.2278    0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420   -0.1552   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -1.5636    1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6690   -0.9455    1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -1.9061    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572    0.3611    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0941    1.2308    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8581    1.2549    2.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9742    0.6830    0.1733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9409    1.5069   -1.0169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2324    0.7260   -2.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2662    2.7842   -0.6435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6122    3.6653   -1.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820    3.4925    0.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7669    2.6316    0.7346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7234   -0.6541    0.2476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9552   -0.5288   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1160    0.0914   -1.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -1.1859    0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4299   -1.0020   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861   -4.4490    1.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -3.8068    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576   -4.3087    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370   -2.4514    3.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -3.6870    3.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1566   -2.2182    4.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091   -0.0388    3.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8164    2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -0.1950    3.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -2.5286    0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -0.5089   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    0.1336   -0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820    0.7390    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800   -2.3970    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5887   -2.8983    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7393   -1.5926    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244   -2.0164   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    0.9061    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7921    1.8212    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2661    1.7130    3.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1438    0.2438    2.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9784    1.6924   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1903    0.5228   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413    1.2709   -3.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -0.2444   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402    3.1731   -2.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2685    4.6031   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3108    3.9172   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421    3.0681    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2415   -1.4236    0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501    0.0631   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4564   -1.4849   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 11 13  2  0
 20 22  1  0
 11 12  1  0
 26  6  1  0
 13 14  1  0
 22 25  1  0
 14 16  2  0
  6  4  2  0
 14 15  1  0
 17 16  1  1
 25 17  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  3 29  2  0
  2  1  1  0
 17 19  1  0
 29 30  1  0
 27 28  2  0
 20 21  1  0
  7  8  1  1
 22 23  1  6
 29 27  1  0
 25 24  1  0
 22 24  1  0
  7 10  1  0
 17 18  1  0
 19 20  1  0
 10 40  1  6
 10 11  1  0
  7  9  1  0
 10  9  1  0
  7  6  1  0
 20 52  1  6
 25 59  1  6
  8 37  1  0
  8 38  1  0
  8 39  1  0
 13 44  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 16 48  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

4-methoxy-3,5-dimethyl-6-[(2R,3S)-2-methyl-3-[(2E,4E)-4-methyl-5-[(1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]penta-2,4-dien-2-yl]oxiran-2-yl]-2H-pyran-2-one

Traditional Name

4-methoxy-3,5-dimethyl-6-[(2R,3S)-2-methyl-3-[(2E,4E)-4-methyl-5-[(1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]penta-2,4-dien-2-yl]oxiran-2-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(\C(=C(/[H])[C@@]1(O[C@]([H])(C([H])([H])[H])[C@]2(O[C@@]12[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])=C(\C([H])([H])[H])[C@]1([H])O[C@]1(C1=C(C(OC([H])([H])[H])=C(C(=O)O1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3/b12-11+,13-10+/t16-,18+,21+,22+,23-,24-/m1/s1

InChI Key

JSVLNARHSWZARV-FOOXNAEUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp.	JEOL database	Choo, S.-J., et al, J. Antibiotics 58, 210 (2005)
Penicillium verrucosum	LOTUS Database	35616633
Talaromyces verruculosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Para-dioxane
Oxolane
Vinylogous ester
Heteroaromatic compound
Lactone
Ether
Oxirane
Dialkyl ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
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	4.53	ALOGPS
logP	3.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.56 m³·mol⁻¹	ChemAxon
Polarizability	45.71 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4941929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verrucosidin

METLIN ID

Not Available

PubChem Compound

6437365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li J, Wang J, Jiang CS, Li G, Guo YW: (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza. J Asian Nat Prod Res. 2014;16(5):542-8. doi: 10.1080/10286020.2014.911290. Epub 2014 Apr 29. [PubMed:24773150 ]
Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M: Penicyrones A and B, an epimeric pair of alpha-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. [PubMed:26243556 ]
Lin TS, Chiang YM, Wang CC: Biosynthetic Pathway of the Reduced Polyketide Product Citreoviridin in Aspergillus terreus var. aureus Revealed by Heterologous Expression in Aspergillus nidulans. Org Lett. 2016 Mar 18;18(6):1366-9. doi: 10.1021/acs.orglett.6b00299. Epub 2016 Mar 8. [PubMed:26954888 ]
Pan C, Shi Y, Auckloo BN, Chen X, Chen CT, Tao X, Wu B: An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10. Mar Drugs. 2016 Aug 18;14(8). pii: md14080156. doi: 10.3390/md14080156. [PubMed:27548192 ]
Valente S, Piombo E, Schroeckh V, Meloni GR, Heinekamp T, Brakhage AA, Spadaro D: CRISPR-Cas9-Based Discovery of the Verrucosidin Biosynthesis Gene Cluster in Penicillium polonicum. Front Microbiol. 2021 May 21;12:660871. doi: 10.3389/fmicb.2021.660871. eCollection 2021. [PubMed:34093475 ]
Cai XY, Wang JP, Shu Y, Hu JT, Sun CT, Cai L, Ding ZT: A new cytotoxic indole alkaloid from the fungus Penicillium polonicum TY12. Nat Prod Res. 2020 Oct 4:1-7. doi: 10.1080/14786419.2020.1828406. [PubMed:33016118 ]
Li W, Ma Z, Chen L, Yin WB: Synthesis and production of the antitumor polyketide aurovertins and structurally related compounds. Appl Microbiol Biotechnol. 2018 Aug;102(15):6373-6381. doi: 10.1007/s00253-018-9123-1. Epub 2018 Jun 2. [PubMed:29860591 ]
Kim HY, Heo do Y, Park HM, Singh D, Lee CH: Metabolomic and Transcriptomic Comparison of Solid-State and Submerged Fermentation of Penicillium expansum KACC 40815. PLoS One. 2016 Feb 10;11(2):e0149012. doi: 10.1371/journal.pone.0149012. eCollection 2016. [PubMed:26863302 ]
Thomas S, Sharma N, Gonzalez R, Pao PW, Hofman FM, Chen TC, Louie SG, Pirrung MC, Schonthal AH: Repositioning of Verrucosidin, a purported inhibitor of chaperone protein GRP78, as an inhibitor of mitochondrial electron transport chain complex I. PLoS One. 2013 Jun 6;8(6):e65695. doi: 10.1371/journal.pone.0065695. Print 2013. [PubMed:23755268 ]
Rodriguez A, Cordoba JJ, Werning ML, Andrade MJ, Rodriguez M: Duplex real-time PCR method with internal amplification control for quantification of verrucosidin producing molds in dry-ripened foods. Int J Food Microbiol. 2012 Feb 1;153(1-2):85-91. doi: 10.1016/j.ijfoodmicro.2011.10.020. Epub 2011 Nov 4. [PubMed:22119450 ]
Choo, S.-J., et al. (2005). Choo, S.-J., et al, J. Antibiotics 58, 210 (2005). J. Antibiotics.

Showing NP-Card for verrucosidin (NP0028161)

MOL for NP0028161 (verrucosidin)

3D MOL for NP0028161 (verrucosidin)

3D SDF for NP0028161 (verrucosidin)

3D-SDF for NP0028161 (verrucosidin)

PDB for NP0028161 (verrucosidin)

3D PDB for NP0028161 (verrucosidin)

SMILES for NP0028161 (verrucosidin)

INCHI for NP0028161 (verrucosidin)

Structure for NP0028161 (verrucosidin)

3D Structure for NP0028161 (verrucosidin)