NP-MRD: Showing NP-Card for Norbikaverin (NP0021575)

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Record Information

Version

2.0

Created at

2021-01-06 06:51:49 UTC

Updated at

2021-07-15 17:36:42 UTC

NP-MRD ID

NP0021575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Norbikaverin

Provided By

NPAtlas

Description

Norbikaverin is found in Fusarium fujikuroi. Norbikaverin was first documented in 1971 (PMID: 5168485). Based on a literature review a small amount of articles have been published on Norbikaverin (PMID: 31748828) (PMID: 20376635) (PMID: 12846324).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 39 42  0  0  0  0            999 V2000
    6.5787   -0.8821    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -1.1650    1.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -0.7039    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.0602   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    0.5455   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.3636   -2.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    0.2358   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797    0.6719   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3706   -2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    0.3490   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -0.4169    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5885   -0.8291    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.5342    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9216   -0.9820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -0.7434    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.4372    2.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -0.2719    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3084   -0.5975    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -1.3636    2.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -0.1696    0.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7040   -0.5122    1.6378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5729    0.5915   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    0.9290   -0.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999    1.6858   -1.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.5024   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8858    0.1854    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3267   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    0.8501   -3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6478    2.3970   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    1.4774   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.5813    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.6718    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -1.0542    2.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5301    0.9333   -0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    2.0236   -2.5188 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
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 22 38  1  0  0  0  0
 24 39  1  0  0  0  0
M  END

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    6.5787   -0.8821    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -1.1650    1.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -0.7039    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.0602   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    0.5455   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.3636   -2.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    0.2358   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797    0.6719   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3706   -2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    0.3490   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5885   -0.8291    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2273   -1.3636    2.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -0.1696    0.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242105163D          

 39 42  0  0  0  0            999 V2000
    6.5787   -0.8821    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -1.1650    1.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -0.7039    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9742    0.5455   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.3636   -2.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    0.2358   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797    0.6719   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3706   -2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
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 13  7  1  0  0  0  0
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  6 32  1  0  0  0  0
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  6 34  1  0  0  0  0
 14 35  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0021575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(OC4=C([H])C(OC([H])([H])[H])=C([H])C(=C4C3=O)C([H])([H])[H])C(=O)C2=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O8/c1-6-3-7(26-2)4-10-11(6)16(23)14-17(24)12-8(20)5-9(21)15(22)13(12)18(25)19(14)27-10/h3-5,20-22H,1-2H3

> <INCHI_KEY>
GOQPBCJYIHERLE-UHFFFAOYSA-N

> <FORMULA>
C19H12O8

> <MOLECULAR_WEIGHT>
368.297

> <EXACT_MASS>
368.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.9384341730604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.1646365873333333

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.963377991084286

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.0372309153757096

> <JCHEM_PKA_STRONGEST_BASIC>
-4.766160039691832

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
93.69099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8,10-trihydroxy-3-methoxy-1-methyl-5-oxatetracene-6,11,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    6.5787   -0.8821    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -1.1650    1.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -0.7039    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.0602   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    0.5455   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.3636   -2.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    0.2358   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797    0.6719   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3706   -2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    0.3490   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -0.4169    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5885   -0.8291    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.5342    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9216   -0.9820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -0.7434    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.4372    2.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -0.2719    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3084   -0.5975    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -1.3636    2.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -0.1696    0.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7040   -0.5122    1.6378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5729    0.5915   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    0.9290   -0.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999    1.6858   -1.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.5024   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    0.8280   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5219   -2.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3682   -1.5187    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691   -1.0498   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8858    0.1854    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3267   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    0.8501   -3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6478    2.3970   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    1.4774   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.5813    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.6718    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -1.0542    2.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5301    0.9333   -0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    2.0236   -2.5188 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
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 17 18  2  0
 18 19  1  0
 18 20  1  0
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 20 22  2  0
 22 23  1  0
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 23 25  2  0
 25 26  1  0
 26 27  2  0
 14  3  1  0
 25 17  1  0
 13  7  1  0
 26 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 14 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 24 39  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       6.579  -0.882   0.578  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.340  -1.165   1.153  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.139  -0.704   0.607  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.150   0.060  -0.541  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.974   0.546  -1.126  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.009   1.364  -2.358  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.778   0.236  -0.516  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.580   0.672  -1.025  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.556   1.371  -2.071  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.612   0.349  -0.395  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.572  -0.417   0.749  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.589  -0.829   1.227  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.727  -0.534   0.646  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.922  -0.982   1.173  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.835  -0.743   1.393  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.868  -1.437   2.438  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.104  -0.272   0.840  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.308  -0.598   1.475  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.227  -1.364   2.615  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.516  -0.170   0.979  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.704  -0.512   1.638  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.573   0.592  -0.156  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.379   0.929  -0.808  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.500   1.686  -1.929  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.163   0.502  -0.316  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.896   0.828  -0.958  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.859   1.522  -2.004  0.00  0.00           O+0
HETATM   28  H   UNK     0       7.368  -1.519   0.978  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.469  -1.050  -0.529  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.886   0.185   0.758  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.057   0.327  -1.051  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.516   0.850  -3.227  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.648   2.397  -2.214  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.092   1.477  -2.658  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.853  -1.581   2.080  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.987  -1.672   3.170  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.779  -1.054   2.460  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.530   0.933  -0.553  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.820   2.024  -2.519  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   32   33   34                                             
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14    7                                                  
CONECT   14   13    3   35                                                  
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   36                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20   37                                                       
CONECT   22   20   23   38                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   39                                                       
CONECT   25   23   26   17                                                  
CONECT   26   25   27   10                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35   14                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   24                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

RDKit          3D

39 42  0  0  0  0  0  0  0  0999 V2000
    6.5787   -0.8821    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3404   -1.1650    1.1532 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -0.7039    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.0602   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742    0.5455   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    1.3636   -2.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    0.2358   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797    0.6719   -1.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3706   -2.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    0.3490   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5724   -0.4169    0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5885   -0.8291    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273   -0.5342    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9216   -0.9820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -0.7434    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -1.4372    2.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -0.2719    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3084   -0.5975    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -1.3636    2.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -0.1696    0.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7040   -0.5122    1.6378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5729    0.5915   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    0.9290   -0.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999    1.6858   -1.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.5024   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    0.8280   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    1.5219   -2.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3682   -1.5187    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691   -1.0498   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8858    0.1854    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.3267   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    0.8501   -3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6478    2.3970   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    1.4774   -2.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.5813    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.6718    3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7788   -1.0542    2.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5301    0.9333   -0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198    2.0236   -2.5188 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 14  3  1  0
 25 17  1  0
 13  7  1  0
 26 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
 14 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 24 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₉H₁₂O₈

Average Mass

368.2970 Da

Monoisotopic Mass

368.05322 Da

IUPAC Name

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

Traditional Name

7,8,10-trihydroxy-3-methoxy-1-methyl-5-oxatetracene-6,11,12-trione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(C)=C1)C(=O)C1=C(O2)C(=O)C2=C(C(O)=CC(O)=C2O)C1=O

InChI Identifier

InChI=1S/C19H12O8/c1-6-3-7(26-2)4-10-11(6)16(23)14-17(24)12-8(20)5-9(21)15(22)13(12)18(25)19(14)27-10/h3-5,20-22H,1-2H3

InChI Key

GOQPBCJYIHERLE-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 fujikuroi	NPAtlas	5168485

Chemical Taxonomy

Classification

Not classified

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	2.93	ALOGPS
logP	3.16	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.04	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.69 m³·mol⁻¹	ChemAxon
Polarizability	35.94 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

NPAtlas ID

NPA006945

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049240

Chemspider ID

78436057

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135565101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kjaer D, Kjaer A, Pedersen C, Bu'lock JD, Smith JR: Bikaverin and norbikaverin, benzoxanthentrione pigments of Gibberella fujikuroi. J Chem Soc Perkin 1. 1971;16:2792-7. doi: 10.1039/j39710002792. [PubMed:5168485 ]
Lebeau J, Petit T, Dufosse L, Caro Y: Putative metabolic pathway for the bioproduction of bikaverin and intermediates thereof in the wild Fusarium oxysporum LCP531 strain. AMB Express. 2019 Nov 20;9(1):186. doi: 10.1186/s13568-019-0912-4. [PubMed:31748828 ]
Limon MC, Rodriguez-Ortiz R, Avalos J: Bikaverin production and applications. Appl Microbiol Biotechnol. 2010 Jun;87(1):21-9. doi: 10.1007/s00253-010-2551-1. Epub 2010 Apr 8. [PubMed:20376635 ]
Bell AA, Wheeler MH, Liu J, Stipanovic RD, Puckhaber LS, Orta H: United States Department of Agriculture-Agricultural Research Service studies on polyketide toxins of Fusarium oxysporum f sp vasinfectum: potential targets for disease control. Pest Manag Sci. 2003 Jun-Jul;59(6-7):736-47. doi: 10.1002/ps.713. [PubMed:12846324 ]

Showing NP-Card for Norbikaverin (NP0021575)

MOL for NP0021575 (Norbikaverin)

3D MOL for NP0021575 (Norbikaverin)

3D SDF for NP0021575 (Norbikaverin)

3D-SDF for NP0021575 (Norbikaverin)

PDB for NP0021575 (Norbikaverin)

3D PDB for NP0021575 (Norbikaverin)

SMILES for NP0021575 (Norbikaverin)

INCHI for NP0021575 (Norbikaverin)

Structure for NP0021575 (Norbikaverin)

3D Structure for NP0021575 (Norbikaverin)