NP-MRD: Showing NP-Card for berkazaphilone C (NP0036526)

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Record Information

Version

2.0

Created at

2021-06-20 19:40:37 UTC

Updated at

2021-06-30 00:08:13 UTC

NP-MRD ID

NP0036526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

berkazaphilone C

Provided By

JEOL Database JEOL Logo

Description

Azaphilone belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. berkazaphilone C is found in Penicillium rubrum. berkazaphilone C was first documented in 2020 (PMID: 33352851). Based on a literature review a small amount of articles have been published on Azaphilone (PMID: 33925595) (PMID: 33643832) (PMID: 33607578) (PMID: 33600149).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121403D          

 50 52  0  0  0  0            999 V2000
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    0.2759    2.4237    4.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3428    1.4017    2.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    1.1277    2.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.3571    1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6211   -0.6329   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8107   -0.7648   -0.6432 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2874   -2.6294   -0.4801 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121403D          

 50 52  0  0  0  0            999 V2000
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   -0.8570    1.6965   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
  8  7  1  0  0  0  0
 10 13  1  0  0  0  0
 13 26  1  0  0  0  0
  6  7  2  0  0  0  0
  6 26  1  0  0  0  0
 17 15  1  0  0  0  0
 23 21  2  0  0  0  0
 15 16  2  0  0  0  0
 17 24  2  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28  4  1  0  0  0  0
  4  5  2  0  0  0  0
 21 20  1  0  0  0  0
  4  3  1  0  0  0  0
 15 14  1  0  0  0  0
  3  2  2  0  0  0  0
 20 18  2  0  0  0  0
  2  1  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
 18 17  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
 21 22  1  0  0  0  0
 26 48  1  1  0  0  0
 10 12  1  1  0  0  0
 23 46  1  0  0  0  0
 20 44  1  0  0  0  0
 22 45  1  0  0  0  0
 25 47  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 12 39  1  0  0  0  0
 13 40  1  6  0  0  0
  7 35  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
  5 34  1  0  0  0  0
  3 33  1  0  0  0  0
  2 32  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C(=O)O[C@]2([H])[C@]3([H])C(C([H])=C(OC3([H])[H])C(\[H])=C(/[H])C([H])([H])[H])=C([H])C(=O)[C@@]2(O[H])C([H])([H])[H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(24)21(3,26)19(15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-9,15,19,22-23,26H,10H2,1-3H3/b5-4+/t15-,19+,21-/m0/s1

> <INCHI_KEY>
HNVJWWBKFFDQAA-NRKPLWJESA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.523856406551744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R,8R,8aR)-7-hydroxy-7-methyl-6-oxo-3-[(1E)-prop-1-en-1-yl]-6,7,8,8a-tetrahydro-1H-isochromen-8-yl 2,4-dihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.252605821333333

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.544817746348123

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.69673022205969

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9903877309539206

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
105.33559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R,8R,8aR)-7-hydroxy-7-methyl-6-oxo-3-[(1E)-prop-1-en-1-yl]-8,8a-dihydro-1H-isochromen-8-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    0.6194    3.1547    5.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759    2.4237    4.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    2.1116    3.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    1.4017    2.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    1.1277    2.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.3571    1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    0.1861    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211   -0.6329   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8107   -0.7648   -0.6432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956   -1.3580   -1.1152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9193   -1.6264   -2.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874   -2.6294   -0.4801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -0.5100   -1.0379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0902   -1.2182   -1.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -0.8728   -2.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.0124   -3.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597   -1.6272   -3.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -2.9377   -2.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -3.7479   -2.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -3.5266   -3.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995   -2.8501   -4.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9329   -3.4830   -4.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729   -1.5805   -4.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -0.9786   -4.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    0.2706   -4.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8273   -0.2241    0.4276 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6432    0.7485    0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.0336    1.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460    4.0830    5.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    2.5383    6.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680    3.4089    6.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1163    2.1404    3.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989    2.4053    4.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4245    1.4636    3.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    0.6069    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558   -2.1956   -2.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -2.2366   -3.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -0.6939   -3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -3.1255   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.4506   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007   -4.8073   -2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -3.3975   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300   -3.7007   -2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -4.5271   -3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -2.8960   -5.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044   -1.0478   -5.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.5242   -4.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.1552    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416    0.3167    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    1.6965   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 24 25  1  0
  8  7  1  0
 10 13  1  0
 13 26  1  0
  6  7  2  0
  6 26  1  0
 17 15  1  0
 23 21  2  0
 15 16  2  0
 17 24  2  0
 18 19  1  0
  6  5  1  0
 26 27  1  0
 27 28  1  0
 28  4  1  0
  4  5  2  0
 21 20  1  0
  4  3  1  0
 15 14  1  0
  3  2  2  0
 20 18  2  0
  2  1  1  0
  8 10  1  0
  8  9  2  0
 18 17  1  0
 10 11  1  0
 13 14  1  0
 21 22  1  0
 26 48  1  1
 10 12  1  1
 23 46  1  0
 20 44  1  0
 22 45  1  0
 25 47  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 12 39  1  0
 13 40  1  6
  7 35  1  0
 27 49  1  0
 27 50  1  0
  5 34  1  0
  3 33  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.619   3.155   5.506  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.276   2.424   4.250  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.978   2.112   3.882  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.343   1.402   2.669  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.626   1.128   2.369  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.993   0.357   1.196  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.272   0.186   0.833  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.621  -0.633  -0.355  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.811  -0.765  -0.643  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.496  -1.358  -1.115  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.919  -1.626  -2.562  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.287  -2.629  -0.480  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.203  -0.510  -1.038  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.090  -1.218  -1.637  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.733  -0.873  -2.891  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.248   0.012  -3.560  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.460  -1.627  -3.360  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.780  -2.938  -2.937  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.079  -3.748  -2.004  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.970  -3.527  -3.407  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.800  -2.850  -4.295  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.933  -3.483  -4.711  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.473  -1.581  -4.745  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.303  -0.979  -4.286  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.049   0.271  -4.796  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.827  -0.224   0.428  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.643   0.749   0.509  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.277   1.034   1.866  0.00  0.00           O+0
HETATM   29  H   UNK     0       1.146   4.083   5.265  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.276   2.538   6.128  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.268   3.409   6.095  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.116   2.140   3.620  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.799   2.405   4.532  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.425   1.464   3.026  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.109   0.607   1.378  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.856  -2.196  -2.599  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.179  -2.237  -3.089  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.074  -0.694  -3.114  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.125  -3.126  -0.555  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.369   0.451  -1.547  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.201  -4.807  -2.027  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.038  -3.397  -0.974  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.130  -3.701  -2.304  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.255  -4.527  -3.086  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.412  -2.896  -5.319  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.104  -1.048  -5.449  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.127   0.524  -4.572  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.521  -1.155   0.926  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.242   0.317   0.029  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.857   1.696  -0.003  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32                                                  
CONECT    3    4    2   33                                                  
CONECT    4   28    5    3                                                  
CONECT    5    6    4   34                                                  
CONECT    6    7   26    5                                                  
CONECT    7    8    6   35                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10   13    8   11   12                                             
CONECT   11   10   36   37   38                                             
CONECT   12   10   39                                                       
CONECT   13   10   26   14   40                                             
CONECT   14   15   13                                                       
CONECT   15   17   16   14                                                  
CONECT   16   15                                                            
CONECT   17   15   24   18                                                  
CONECT   18   19   20   17                                                  
CONECT   19   18   41   42   43                                             
CONECT   20   21   18   44                                                  
CONECT   21   23   20   22                                                  
CONECT   22   21   45                                                       
CONECT   23   24   21   46                                                  
CONECT   24   23   25   17                                                  
CONECT   25   24   47                                                       
CONECT   26   13    6   27   48                                             
CONECT   27   26   28   49   50                                             
CONECT   28   27    4                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    0.6194    3.1547    5.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759    2.4237    4.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9775    2.1116    3.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    1.4017    2.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    1.1277    2.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.3571    1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    0.1861    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211   -0.6329   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8107   -0.7648   -0.6432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956   -1.3580   -1.1152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9193   -1.6264   -2.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874   -2.6294   -0.4801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -0.5100   -1.0379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0902   -1.2182   -1.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -0.8728   -2.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.0124   -3.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597   -1.6272   -3.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -2.9377   -2.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0786   -3.7479   -2.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -3.5266   -3.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995   -2.8501   -4.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9329   -3.4830   -4.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729   -1.5805   -4.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -0.9786   -4.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    0.2706   -4.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8273   -0.2241    0.4276 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6432    0.7485    0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.0336    1.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460    4.0830    5.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    2.5383    6.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680    3.4089    6.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1163    2.1404    3.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989    2.4053    4.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4245    1.4636    3.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    0.6069    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558   -2.1956   -2.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -2.2366   -3.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -0.6939   -3.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -3.1255   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690    0.4506   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007   -4.8073   -2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378   -3.3975   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300   -3.7007   -2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -4.5271   -3.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -2.8960   -5.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044   -1.0478   -5.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.5242   -4.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207   -1.1552    0.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2416    0.3167    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    1.6965   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 24 25  1  0
  8  7  1  0
 10 13  1  0
 13 26  1  0
  6  7  2  0
  6 26  1  0
 17 15  1  0
 23 21  2  0
 15 16  2  0
 17 24  2  0
 18 19  1  0
  6  5  1  0
 26 27  1  0
 27 28  1  0
 28  4  1  0
  4  5  2  0
 21 20  1  0
  4  3  1  0
 15 14  1  0
  3  2  2  0
 20 18  2  0
  2  1  1  0
  8 10  1  0
  8  9  2  0
 18 17  1  0
 10 11  1  0
 13 14  1  0
 21 22  1  0
 26 48  1  1
 10 12  1  1
 23 46  1  0
 20 44  1  0
 22 45  1  0
 25 47  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 12 39  1  0
 13 40  1  6
  7 35  1  0
 27 49  1  0
 27 50  1  0
  5 34  1  0
  3 33  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

(7R,8R,8aR)-7-hydroxy-7-methyl-6-oxo-3-[(1E)-prop-1-en-1-yl]-6,7,8,8a-tetrahydro-1H-isochromen-8-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

(7R,8R,8aR)-7-hydroxy-7-methyl-6-oxo-3-[(1E)-prop-1-en-1-yl]-8,8a-dihydro-1H-isochromen-8-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C(C(=O)O[C@]2([H])[C@]3([H])C(C([H])=C(OC3([H])[H])C(\[H])=C(/[H])C([H])([H])[H])=C([H])C(=O)[C@@]2(O[H])C([H])([H])[H])C(=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(24)21(3,26)19(15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-9,15,19,22-23,26H,10H2,1-3H3/b5-4+/t15-,19+,21-/m0/s1

InChI Key

HNVJWWBKFFDQAA-NRKPLWJESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Talaromyces ruber	JEOL database	Stierle, A. A., et al, J. Nat. Prod. 75, 344 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoyl
M-cresol
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Toluene
Acyloin
Tertiary alcohol
Vinylogous acid
Ketone
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	2.72	ALOGPS
logP	3.25	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.34 m³·mol⁻¹	ChemAxon
Polarizability	40.52 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	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

28531479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57384025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Venkatachalam M, Shum-Cheong-Sing A, Caro Y, Dufosse L, Fouillaud M: OVAT Analysis and Response Surface Methodology Based on Nutrient Sources for Optimization of Pigment Production in the Marine-Derived Fungus Talaromyces albobiverticillius 30548 Submerged Fermentation. Mar Drugs. 2021 Apr 27;19(5). pii: md19050248. doi: 10.3390/md19050248. [PubMed:33925595 ]
Wei Q, Bai J, Yan D, Bao X, Li W, Liu B, Zhang D, Qi X, Yu D, Hu Y: Genome mining combined metabolic shunting and OSMAC strategy of an endophytic fungus leads to the production of diverse natural products. Acta Pharm Sin B. 2021 Feb;11(2):572-587. doi: 10.1016/j.apsb.2020.07.020. Epub 2020 Aug 5. [PubMed:33643832 ]
Zhang XY, Tan XM, Yu M, Yang J, Sun BD, Qin JC, Guo LP, Ding G: Bioactive metabolites from the desert plant-associated endophytic fungus Chaetomium globosum (Chaetomiaceae). Phytochemistry. 2021 May;185:112701. doi: 10.1016/j.phytochem.2021.112701. Epub 2021 Feb 16. [PubMed:33607578 ]
Chakrabarty S, Romero EO, Pyser JB, Yazarians JA, Narayan ARH: Chemoenzymatic Total Synthesis of Natural Products. Acc Chem Res. 2021 Mar 16;54(6):1374-1384. doi: 10.1021/acs.accounts.0c00810. Epub 2021 Feb 18. [PubMed:33600149 ]
Lebeau J, Petit T, Fouillaud M, Dufosse L, Caro Y: Aqueous Two-Phase System Extraction of Polyketide-Based Fungal Pigments Using Ammonium- or Imidazolium-Based Ionic Liquids for Detection Purpose: A Case Study. J Fungi (Basel). 2020 Dec 18;6(4). pii: jof6040375. doi: 10.3390/jof6040375. [PubMed:33352851 ]
Stierle, A. A., et al. (2012). Stierle, A. A., et al, J. Nat. Prod. 75, 344 (2012). J. Nat. Prod..

Showing NP-Card for berkazaphilone C (NP0036526)

MOL for NP0036526 (berkazaphilone C)

3D MOL for NP0036526 (berkazaphilone C)

3D SDF for NP0036526 (berkazaphilone C)

3D-SDF for NP0036526 (berkazaphilone C)

PDB for NP0036526 (berkazaphilone C)

3D PDB for NP0036526 (berkazaphilone C)

SMILES for NP0036526 (berkazaphilone C)

INCHI for NP0036526 (berkazaphilone C)

Structure for NP0036526 (berkazaphilone C)

3D Structure for NP0036526 (berkazaphilone C)