NP-MRD: Showing NP-Card for Verrulactone A (NP0010671)

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Record Information

Version

2.0

Created at

2021-01-05 20:06:43 UTC

Updated at

2026-02-05 16:11:39 UTC

NP-MRD ID

NP0010671

Natural Product DOI

https://doi.org/10.57994/5424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verrulactone A

Provided By

NPAtlas

Description

Verrulactone A belongs to the class of organic compounds known as biphenols. These are organic compounds containing two phenol groups linked together by a C-C bond. Verrulactone A is found in Penicillium and Talaromyces verruculosus. Verrulactone A was first documented in 2012 (PMID: 22377515). Based on a literature review very few articles have been published on Verrulactone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107403D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242107403D          

 58 63  0  0  0  0            999 V2000
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   -1.8015    2.1425   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    2.6589   -2.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    2.0200   -3.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    0.9936   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.5218    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463   -0.6187    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -0.5741   -0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2014    0.1208    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173    0.2845    1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    0.9595    4.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -0.4539    3.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8921    2.0374    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921    2.3367    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138   -1.4367   -4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2486   -3.9339    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304   -4.2673    3.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -2.4497    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188    3.6720   -0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069    3.6446   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    1.9105   -2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    0.9809   -3.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    2.5536   -3.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608    0.6383   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.0218    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 17 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40  3  1  0  0  0  0
 39  7  1  0  0  0  0
 38 11  1  0  0  0  0
 37 18  1  0  0  0  0
 37 24  2  0  0  0  0
 36 28  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  4 44  1  0  0  0  0
  6 45  1  0  0  0  0
 12 46  1  0  0  0  0
 14 47  1  0  0  0  0
 16 48  1  0  0  0  0
 20 49  1  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  0  0  0  0
 30 52  1  0  0  0  0
 31 53  1  0  0  0  0
 34 54  1  0  0  0  0
 34 55  1  0  0  0  0
 34 56  1  0  0  0  0
 35 57  1  0  0  0  0
 40 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C3=C([H])C(OC([H])([H])[H])=C([H])C(O[H])=C3C(=O)O2)C(=C1O[H])C1=C2C(OC(=O)C3=C(O[H])C([H])=C(OC([H])([H])[H])C([H])=C23)=C([H])C(O[H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H18O12/c1-37-9-3-11-19(13(29)5-9)27(35)39-17-7-15(31)25(33)23(21(11)17)24-22-12-4-10(38-2)6-14(30)20(12)28(36)40-18(22)8-16(32)26(24)34/h3-8,29-34H,1-2H3

> <INCHI_KEY>
ZSHZQCWUSDSOFB-UHFFFAOYSA-N

> <FORMULA>
C28H18O12

> <MOLECULAR_WEIGHT>
546.44

> <EXACT_MASS>
546.07982602

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
51.191257871720985

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,7-trihydroxy-9-methoxy-1-{2,3,7-trihydroxy-9-methoxy-6-oxo-6H-benzo[c]chromen-1-yl}-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
4.687899967333332

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.850127254300569

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.246745515503323

> <JCHEM_PKA_STRONGEST_BASIC>
-4.077302192360649

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
137.76819999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,7-trihydroxy-9-methoxy-1-{2,3,7-trihydroxy-9-methoxy-6-oxobenzo[c]chromen-1-yl}benzo[c]chromen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
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    0.9868   -3.1358    0.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4524   -1.0467    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.4078    2.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.6392    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0637    1.2131    1.8718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2765    1.1362    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073    2.2689   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863    2.8352    0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    2.7595   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    2.1425   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    2.6589   -2.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    2.0200   -3.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    0.9936   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.5218    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463   -0.6187    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -0.5741   -0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2014    0.1208    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173    0.2845    1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    0.9595    4.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -0.4539    3.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    1.0005    2.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.0374    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921    2.3367    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138   -1.4367   -4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -3.0139   -4.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407   -2.8511   -2.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -3.9339    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304   -4.2673    3.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -2.4497    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188    3.6720   -0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069    3.6446   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1563    0.9809   -3.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5686   -0.0218    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 17 38  2  0
 38 39  1  0
 39 40  2  0
 40  3  1  0
 39  7  1  0
 38 11  1  0
 37 18  1  0
 37 24  2  0
 36 28  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  4 44  1  0
  6 45  1  0
 12 46  1  0
 14 47  1  0
 16 48  1  0
 20 49  1  0
 22 50  1  0
 23 51  1  0
 30 52  1  0
 31 53  1  0
 34 54  1  0
 34 55  1  0
 34 56  1  0
 35 57  1  0
 40 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       0.145   0.645   3.759  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.458   1.176   3.595  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.131   0.993   2.398  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.394   1.492   2.211  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.074   1.321   1.032  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.347   1.819   0.829  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.481   0.631   0.008  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.128   0.455  -1.197  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.280   0.924  -1.342  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.546  -0.188  -2.160  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.329  -0.698  -2.040  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.817  -1.359  -3.121  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.558  -1.907  -3.034  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.085  -2.563  -4.154  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.147  -1.783  -1.878  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.430  -2.361  -1.834  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.336  -1.108  -0.726  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.501  -1.262   0.392  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.175  -2.393   1.179  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.987  -3.136   0.904  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.939  -2.826   2.223  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.555  -3.958   2.963  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.086  -2.165   2.560  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.452  -1.047   1.821  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.554  -0.408   2.138  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.998   0.639   1.528  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.064   1.213   1.872  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.276   1.136   0.468  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.707   2.269  -0.208  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.886   2.835   0.233  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.965   2.760  -1.250  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.802   2.143  -1.631  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.073   2.659  -2.684  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.126   2.020  -3.073  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.351   0.994  -0.958  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.102   0.522   0.069  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.646  -0.619   0.751  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.587  -0.574  -0.856  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.201   0.121   0.191  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.517   0.285   1.348  0.00  0.00           C+0
HETATM   41  H   UNK     0      -0.307   0.960   4.703  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.230  -0.454   3.669  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.519   1.000   2.945  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.892   2.037   2.994  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.792   2.337   1.599  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.414  -1.437  -4.026  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.793  -3.014  -4.267  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.841  -2.851  -2.599  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.249  -3.934   1.433  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.130  -4.267   3.732  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.730  -2.450   3.364  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.219   3.672  -0.254  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.307   3.645  -1.777  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.843   1.911  -2.226  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.156   0.981  -3.364  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.657   2.554  -3.868  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.461   0.638  -1.301  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.569  -0.022   1.554  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5   44                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   45                                                       
CONECT    7    5    8   39                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13   46                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   47                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15   48                                                       
CONECT   17   15   18   38                                                  
CONECT   18   17   19   37                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   49                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21   50                                                       
CONECT   23   21   24   51                                                  
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   52                                                       
CONECT   31   29   32   53                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   54   55   56                                             
CONECT   35   32   36   57                                                  
CONECT   36   35   37   28                                                  
CONECT   37   36   18   24                                                  
CONECT   38   17   39   11                                                  
CONECT   39   38   40    7                                                  
CONECT   40   39    3   58                                                  
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    4                                                            
CONECT   45    6                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   16                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   34                                                            
CONECT   55   34                                                            
CONECT   56   34                                                            
CONECT   57   35                                                            
CONECT   58   40                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

RDKit          3D

58 63  0  0  0  0  0  0  0  0999 V2000
    0.1450    0.6453    3.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583    1.1762    3.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1305    0.9932    2.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3936    1.4919    2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744    1.3208    1.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470    1.8185    0.8289 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806    0.6306    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282    0.4547   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    0.9236   -1.3416 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5459   -0.1877   -2.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -0.6982   -2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -1.3585   -3.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -1.9074   -3.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -2.5635   -4.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1472   -1.7829   -1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301   -2.3614   -1.8342 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361   -1.1079   -0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5013   -1.2617    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747   -2.3935    1.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -3.1358    0.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389   -2.8262    2.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547   -3.9585    2.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856   -2.1646    2.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -1.0467    1.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5537   -0.4078    2.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9981    0.6392    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0637    1.2131    1.8718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2765    1.1362    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073    2.2689   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8863    2.8352    0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    2.7595   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    2.1425   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    2.6589   -2.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    2.0200   -3.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    0.9936   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1016    0.5218    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6463   -0.6187    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -0.5741   -0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2014    0.1208    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173    0.2845    1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    0.9595    4.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -0.4539    3.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189    1.0005    2.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.0374    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921    2.3367    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138   -1.4367   -4.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -3.0139   -4.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407   -2.8511   -2.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -3.9339    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304   -4.2673    3.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -2.4497    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188    3.6720   -0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069    3.6446   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    1.9105   -2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    0.9809   -3.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    2.5536   -3.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4608    0.6383   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.0218    1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  2  0
 36 37  1  0
 17 38  2  0
 38 39  1  0
 39 40  2  0
 40  3  1  0
 39  7  1  0
 38 11  1  0
 37 18  1  0
 37 24  2  0
 36 28  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  4 44  1  0
  6 45  1  0
 12 46  1  0
 14 47  1  0
 16 48  1  0
 20 49  1  0
 22 50  1  0
 23 51  1  0
 30 52  1  0
 31 53  1  0
 34 54  1  0
 34 55  1  0
 34 56  1  0
 35 57  1  0
 40 58  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₈H₁₈O₁₂

Average Mass

546.4400 Da

Monoisotopic Mass

546.07983 Da

IUPAC Name

2,3,7-trihydroxy-9-methoxy-1-{2,3,7-trihydroxy-9-methoxy-6-oxo-6H-benzo[c]chromen-1-yl}-6H-benzo[c]chromen-6-one

Traditional Name

2,3,7-trihydroxy-9-methoxy-1-{2,3,7-trihydroxy-9-methoxy-6-oxobenzo[c]chromen-1-yl}benzo[c]chromen-6-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)OC3=CC(O)=C(O)C(C4=C5C(OC(=O)C6=C(O)C=C(OC)C=C56)=CC(O)=C4O)=C3C2=C1

InChI Identifier

InChI=1S/C28H18O12/c1-37-9-3-11-19(13(29)5-9)27(35)39-17-7-15(31)25(33)23(21(11)17)24-22-12-4-10(38-2)6-14(30)20(12)28(36)40-18(22)8-16(32)26(24)34/h3-8,29-34H,1-2H3

InChI Key

ZSHZQCWUSDSOFB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, 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, 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
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-05	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	22377515
Penicillium verruculosum F375		Not Available
Talaromyces verruculosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenols. These are organic compounds containing two phenol groups linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenols

Direct Parent

Biphenols

Alternative Parents

Substituents

Biphenol
6,7-dihydroxycoumarin
Isocoumarin
Coumarin
1-benzopyran
2-benzopyran
Benzopyran
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyran
Vinylogous acid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.66	ALOGPS
logP	4.69	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.77 m³·mol⁻¹	ChemAxon
Polarizability	51.19 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009019

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28289569

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verrulactone

METLIN ID

Not Available

PubChem Compound

57404538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim N, Sohn MJ, Kim CJ, Kwon HJ, Kim WG: Verrulactones A and B, new inhibitors of Staphylococcus aureus enoyl-ACP reductase produced by Penicillium verruculosum F375. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2503-6. doi: 10.1016/j.bmcl.2012.02.001. Epub 2012 Feb 9. [PubMed:22377515 ]
DOI: 10.1016/j.bmcl.2012.02.001
PMID: 22377515

Showing NP-Card for Verrulactone A (NP0010671)

MOL for NP0010671 (Verrulactone A)

3D MOL for NP0010671 (Verrulactone A)

3D SDF for NP0010671 (Verrulactone A)

3D-SDF for NP0010671 (Verrulactone A)

PDB for NP0010671 (Verrulactone A)

3D PDB for NP0010671 (Verrulactone A)

SMILES for NP0010671 (Verrulactone A)

INCHI for NP0010671 (Verrulactone A)

Structure for NP0010671 (Verrulactone A)

3D Structure for NP0010671 (Verrulactone A)