NP-MRD: Showing NP-Card for Bikaverin (NP0051590)

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Record Information

Version

2.0

Created at

2022-04-27 22:53:54 UTC

Updated at

2022-04-27 22:53:54 UTC

NP-MRD ID

NP0051590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bikaverin

Description

Bikaverin, also known as lycopersin, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Bikaverin is an extremely weak basic (essentially neutral) compound (based on its pKa). Bikaverin is found in Fusarium bulbigenum, Gibberella fujikuroi, Fusarium oxysporum var. lycopersici, Fusarium solani var. pisi, Fusarium vanettenii and Verticillium agaricinum. Bikaverin was first documented in 2014 (PMID: 24183988). A organic heterotetracyclic compound that is 10H-benzoxanthene-7,10,12-trione substituted by hydroxy groups at positions 6 and 11, methoxy groups at positions 3 and 8 and a methyl group at position 1 (PMID: 24291181).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503362D          

 28 31  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -7.1638    0.6658    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4327   -0.5051    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -0.3562   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.1398   -1.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6106    0.0213   -1.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4439    0.2272   -3.1092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646   -0.0614   -0.9725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -0.2854    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551   -0.3581    1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.5782    2.5391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -0.1966    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7655   -0.2683    1.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -0.1331    1.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -0.2201    1.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358   -0.0746    1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3906   -0.1586    2.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7253   -0.0142    1.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.1540    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526    0.2421   -0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    0.4821   -2.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544    0.0922   -0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    0.1770   -1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975    0.3819   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.0277   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2068    0.1048   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963    0.3221   -2.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -0.4435    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2015   -0.6481    2.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5795    1.2057    1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1391    0.4358    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2765    1.3106   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7894   -0.0728   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343   -0.7177    3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422   -0.3974    2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8309    1.0183    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4066   -0.1699    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9233   -0.7420    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072    0.2700   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009    1.4587   -2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5006   -0.3701   -2.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8936    0.5617   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    0.4571   -3.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8 27  1  0
 27 28  2  0
 27  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7 25  2  0
 25 26  1  0
 14 15  1  0
  7  8  1  0
 13 21  1  0
 25 24  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 14 34  1  0
 10 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
 26 42  1  0
M  END


  Mrv1533004181503362D          

 28 31  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C2C(=O)C3=C(OC2=C1)C(O)=C1C(=O)C(OC)=CC(=O)C1=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3

> <INCHI_KEY>
ZOQMSOSJEWBMHP-UHFFFAOYSA-N

> <FORMULA>
C20H14O8

> <MOLECULAR_WEIGHT>
382.324

> <EXACT_MASS>
382.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
37.66228069392958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,11-dihydroxy-3,8-dimethoxy-1-methyl-10,12-dihydro-7H-5-oxatetracene-7,10,12-trione

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.7735015433333334

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.055584799604437

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1456617940735585

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7549613058483113

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
99.12629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bikaverin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   13   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   10   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   27                                                  
CONECT   27   26    3   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Lycopersin	ChEBI

Chemical Formula

C₂₀H₁₄O₈

Average Mass

382.3240 Da

Monoisotopic Mass

382.06887 Da

IUPAC Name

6,11-dihydroxy-3,8-dimethoxy-1-methyl-10,12-dihydro-7H-5-oxatetracene-7,10,12-trione

Traditional Name

bikaverin

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C2C(=O)C3=C(OC2=C1)C(O)=C1C(=O)C(OC)=CC(=O)C1=C3O

InChI Identifier

InChI=1S/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3

InChI Key

ZOQMSOSJEWBMHP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium bulbigenum	Fungi	KNApSAcK
Fusarium fujikuroi	Fungi	KNApSAcK
Fusarium oxysporum var. lycopersici	Fungi	KNApSAcK
Fusarium solani var. pisi	Fungi	KNApSAcK
Fusarium vanettenii	LOTUS Database	35616633
Verticillium agaricinum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Naphthopyranone
Xanthone
Naphthopyran
Naphthoquinone
Chromone
Naphthalene
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Vinylogous acid
Vinylogous ester
Heteroaromatic compound
Ketone
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:3096 )
aromatic ether (CHEBI:3096 )
organic heterotetracyclic compound (CHEBI:3096 )
polyphenol (CHEBI:3096 )
cyclic ether (CHEBI:3096 )
Naphthopyrones (C10306 )

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	2.89	ALOGPS
logP	3.77	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.13 m³·mol⁻¹	ChemAxon
Polarizability	37.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002798

Chemspider ID

Not Available

KEGG Compound ID

C10306

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281730

PDB ID

Not Available

ChEBI ID

3096

Good Scents ID

Not Available

References

General References

Deshmukh R, Mathew A, Purohit HJ: Characterization of antibacterial activity of bikaverin from Fusarium sp. HKF15. J Biosci Bioeng. 2014 Apr;117(4):443-8. doi: 10.1016/j.jbiosc.2013.09.017. Epub 2013 Oct 31. [PubMed:24183988 ]
Sorensen JL, Sondergaard TE: The effects of different yeast extracts on secondary metabolite production in Fusarium. Int J Food Microbiol. 2014 Jan 17;170:55-60. doi: 10.1016/j.ijfoodmicro.2013.10.024. Epub 2013 Nov 4. [PubMed:24291181 ]

Showing NP-Card for Bikaverin (NP0051590)

MOL for NP0051590 (Bikaverin)

3D MOL for NP0051590 (Bikaverin)

3D SDF for NP0051590 (Bikaverin)

3D-SDF for NP0051590 (Bikaverin)

PDB for NP0051590 (Bikaverin)

3D PDB for NP0051590 (Bikaverin)

SMILES for NP0051590 (Bikaverin)

INCHI for NP0051590 (Bikaverin)

Structure for NP0051590 (Bikaverin)

3D Structure for NP0051590 (Bikaverin)