NP-MRD: Showing NP-Card for Versicoumarin A (NP0044002)

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Record Information

Version

1.0

Created at

2021-06-22 17:44:52 UTC

Updated at

2021-06-22 17:44:52 UTC

NP-MRD ID

NP0044002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Versicoumarin A

Description

Versicoumarin A belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Versicoumarin A is found in Aspergillus versicolor. It was first documented in 2021 (PMID: 34607427). Based on a literature review a significant number of articles have been published on Versicoumarin A (PMID: 34588859) (PMID: 34569051) (PMID: 34553697) (PMID: 34552118).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0044002
     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.6514    4.0778   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    2.6870   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.8450   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990    2.2892   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759    1.3965   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.0488   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083   -0.4009   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    0.4925   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -0.0920   -0.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -1.2655    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -0.9481    1.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081   -1.8241   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782   -2.3131    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2882   -1.8078   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531   -2.6374   -0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822   -0.9015   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -0.2385    0.3682 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8188   -1.2223    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    0.9538   -0.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302    1.8895   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    3.1438   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    4.3716    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    4.6490   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    4.2371   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518    3.3566   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.1427    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843   -1.5297    1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -1.2804    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472   -2.8421   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7407   -1.1046   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7439   -1.7648   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110   -2.7299    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -3.1509   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.5728   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -1.5813    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    0.0059    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6017   -1.9999    1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.6774    0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -1.7019   -0.6977 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 20  5  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END


  Mrv1652306222119442D          

 21 23  0  0  1  0            999 V2000
   -0.1105   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -1.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(C)(C)CC(=O)C2=C2C[C@@H](C)OC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O5/c1-8-5-9-10(15(18)20-8)6-12(19-4)14-13(9)11(17)7-16(2,3)21-14/h6,8H,5,7H2,1-4H3/t8-/m1/s1

> <INCHI_KEY>
KWFWITMTZVXDQD-MRVPVSSYSA-N

> <FORMULA>
C16H18O5

> <MOLECULAR_WEIGHT>
290.315

> <EXACT_MASS>
290.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.31032069496885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-9-methoxy-4,12,12-trimethyl-5,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-triene-6,14-dione

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.1109847503333334

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.522582132398309

> <JCHEM_PKA_STRONGEST_BASIC>
-4.654088796217567

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
76.3382

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-9-methoxy-4,12,12-trimethyl-5,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-triene-6,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0044002
     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.6514    4.0778   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    2.6870   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.8450   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990    2.2892   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759    1.3965   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.0488   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083   -0.4009   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    0.4925   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -0.0920   -0.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -1.2655    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -0.9481    1.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081   -1.8241   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782   -2.3131    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2882   -1.8078   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531   -2.6374   -0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822   -0.9015   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -0.2385    0.3682 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8188   -1.2223    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    0.9538   -0.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302    1.8895   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    3.1438   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    4.3716    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    4.6490   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    4.2371   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518    3.3566   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.1427    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843   -1.5297    1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -1.2804    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472   -2.8421   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7407   -1.1046   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7439   -1.7648   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110   -2.7299    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -3.1509   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.5728   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -1.5813    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    0.0059    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6017   -1.9999    1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.6774    0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -1.7019   -0.6977 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 20  5  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.206  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.724  -5.184   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.206  -3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.184  -7.851   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724  -7.851   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.853  -3.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.853  -4.573   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20   21                                             
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
CONECT   18   12   19                                                       
CONECT   19   18                                                            
CONECT   20    9                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    NP0044002
HETATM    1  C1  UNL     1      -1.651   4.078  -0.747  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.901   2.687  -0.657  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.815   1.845  -0.549  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.499   2.289  -0.524  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.576   1.396  -0.412  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.336   0.049  -0.324  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.008  -0.401  -0.350  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.064   0.493  -0.462  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.318  -0.092  -0.474  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.661  -1.265   0.232  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.994  -0.948   1.689  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.908  -1.824  -0.425  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.578  -2.313   0.258  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.288  -1.808  -0.273  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.553  -2.637  -0.661  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.382  -0.901  -0.195  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.652  -0.238   0.368  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.819  -1.222   0.289  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.942   0.954  -0.306  1.00  0.00           O  
HETATM   20  C16 UNL     1       2.930   1.890  -0.404  1.00  0.00           C  
HETATM   21  O5  UNL     1       3.193   3.144  -0.484  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.186   4.372   0.233  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.592   4.649  -0.909  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.920   4.237  -1.552  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.652   3.357  -0.595  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.109   0.143   1.855  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.884  -1.530   1.976  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.166  -1.280   2.369  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.147  -2.842  -0.090  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.741  -1.105  -0.224  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.744  -1.765  -1.540  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.411  -2.730   1.273  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.885  -3.151  -0.404  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.701  -1.573  -0.947  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.082  -1.581   0.674  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.534   0.006   1.437  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.602  -2.000   1.067  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.742  -0.677   0.488  1.00  0.00           H  
HETATM   39  H18 UNL     1       4.761  -1.702  -0.698  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   20
CONECT    6    7   16
CONECT    7    8    8   14
CONECT    8    9
CONECT    9   10
CONECT   10   11   12   13
CONECT   11   26   27   28
CONECT   12   29   30   31
CONECT   13   14   32   33
CONECT   14   15   15
CONECT   16   17   34   35
CONECT   17   18   19   36
CONECT   18   37   38   39
CONECT   19   20
CONECT   20   21   21
END

NP0044002
     RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -1.6514    4.0778   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012    2.6870   -0.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    1.8450   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990    2.2892   -0.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759    1.3965   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.0488   -0.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0083   -0.4009   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    0.4925   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177   -0.0920   -0.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -1.2655    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944   -0.9481    1.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081   -1.8241   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782   -2.3131    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2882   -1.8078   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531   -2.6374   -0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822   -0.9015   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -0.2385    0.3682 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8188   -1.2223    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    0.9538   -0.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9302    1.8895   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1933    3.1438   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    4.3716    0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    4.6490   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    4.2371   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518    3.3566   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093    0.1427    1.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843   -1.5297    1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -1.2804    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472   -2.8421   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7407   -1.1046   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7439   -1.7648   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110   -2.7299    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -3.1509   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013   -1.5728   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815   -1.5813    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    0.0059    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6017   -1.9999    1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -0.6774    0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606   -1.7019   -0.6977 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 20  5  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₅

Average Mass

290.3150 Da

Monoisotopic Mass

290.11542 Da

IUPAC Name

(4R)-9-methoxy-4,12,12-trimethyl-5,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-triene-6,14-dione

Traditional Name

(4R)-9-methoxy-4,12,12-trimethyl-5,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-triene-6,14-dione

CAS Registry Number

Not Available

SMILES

COC1=C2OC(C)(C)CC(=O)C2=C2C[C@@H](C)OC(=O)C2=C1

InChI Identifier

InChI=1S/C16H18O5/c1-8-5-9-10(15(18)20-8)6-12(19-4)14-13(9)11(17)7-16(2,3)21-14/h6,8H,5,7H2,1-4H3/t8-/m1/s1

InChI Key

KWFWITMTZVXDQD-MRVPVSSYSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus versicolor	Linigton's dataset	Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Ya...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Chromone
2-benzopyran
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Lactone
Ketone
Carboxylic acid ester
Ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	2.4	ALOGPS
logP	2.11	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.34 m³·mol⁻¹	ChemAxon
Polarizability	30.31 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

58923304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101890346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jabborova D, Annapurna K, Al-Sadi AM, Alharbi SA, Datta R, Zuan ATK: Biochar and Arbuscular mycorrhizal fungi mediated enhanced drought tolerance in Okra (Abelmoschus esculentus) plant growth, root morphological traits and physiological properties. Saudi J Biol Sci. 2021 Oct;28(10):5490-5499. doi: 10.1016/j.sjbs.2021.08.016. Epub 2021 Aug 11. [PubMed:34588859 ]
Hanks JE, Larsen J, Campbell A: Factors associated with small lungworm infections in heavily infected sheep in southeast South Australia. Aust Vet J. 2021 Sep 26. doi: 10.1111/avj.13123. [PubMed:34569051 ]
Kharshiing G, Chrungoo NK: Wx alleles in rice: relationship with apparent amylose content of starch and a possible role in rice domestication. J Genet. 2021;100. [PubMed:34553697 ]
Zeng YT, Liu WY, Torng PC, Hwu WL, Lee NC, Lin CY, Chien YH: A pilot study shows the positive effects of continuous airway pressure for treating hypernasal speech in children with infantile-onset Pompe disease. Sci Rep. 2021 Sep 22;11(1):18826. doi: 10.1038/s41598-021-97877-1. [PubMed:34552118 ]
Sun G, Zheng X, Xu K, Song Y, Zhang J: Photodissociation Dynamics of Vinoxy Radical via the B(2)A'' State: The H + CH2CO Product Channel. J Phys Chem A. 2021 Oct 4. doi: 10.1021/acs.jpca.1c07099. [PubMed:34607427 ]
Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Yang, Xue-Mei Li and Qiu-Fen Hu (2014). Yan-qing Ye, Cong-Fang Xia, Juan-Xia Yang, Ying Qin, Ming Zhou, Xue-Mei Gao, Gang Du, Hai-Ying Yang, Xue-Mei Li and Qiu-Fen Hu. Isocoumarins from the fermentation products of an endophytic fungus of Aspergillus versicolor DOI: 10.1016/j.phytol.2014.09.016. Phytochemistry Letters.

Showing NP-Card for Versicoumarin A (NP0044002)

MOL for NP0044002 (Versicoumarin A)

3D MOL for NP0044002 (Versicoumarin A)

3D SDF for NP0044002 (Versicoumarin A)

3D-SDF for NP0044002 (Versicoumarin A)

PDB for NP0044002 (Versicoumarin A)

3D PDB for NP0044002 (Versicoumarin A)

SMILES for NP0044002 (Versicoumarin A)

INCHI for NP0044002 (Versicoumarin A)

Structure for NP0044002 (Versicoumarin A)

3D Structure for NP0044002 (Versicoumarin A)