NP-MRD: Showing NP-Card for hydroxyversicolorone (NP0260367)

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Record Information

Version

2.0

Created at

2022-09-08 02:31:00 UTC

Updated at

2022-09-08 02:31:00 UTC

NP-MRD ID

NP0260367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hydroxyversicolorone

Description

Hydroxyversicolorone belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Hydroxyversicolorone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. hydroxyversicolorone was first documented in 2003 (PMID: 12513978). Based on a literature review a significant number of articles have been published on hydroxyversicolorone (PMID: 15184162) (PMID: 15933021) (PMID: 19211038) (PMID: 30563144) (PMID: 22069531).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204312D          

 28 31  0  0  1  0            999 V2000
    7.1953   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363   -2.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3814    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  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
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    5.5788   -1.3634   -1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2581   -1.7627   -0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -2.4437   -1.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -1.3210    0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204    0.1558    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351    0.8326   -0.1324 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2950    0.6983   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.9317   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    2.1657   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4587    1.2154   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -0.0126   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2998   -0.2568    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026   -1.4511    0.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853   -1.0054    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -2.1345    0.5737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -0.7178   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4952   -1.6499    0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -2.8969    0.6528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8298   -1.3351   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2264   -0.0964   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5644    0.1832   -0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2245    0.8218   -0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8877    0.5026   -0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682    1.5073   -0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.6229   -1.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570    2.7899   -0.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    2.3687    0.2182 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1082    2.8259    0.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4811   -0.5711   -1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1702   -2.1772   -1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2136   -0.8791   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7554   -1.5561    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469   -1.9063    1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701    0.5856    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    0.4426    1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    0.8455   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    3.1329   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728   -2.2994    0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7850   -3.6302    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5859   -2.0594    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1836    0.5691   -0.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4804    1.7966   -1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    2.5006    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4836    3.0313    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 27  1  0
 27 28  1  0
 27 26  1  0
 26  8  1  0
  8  7  2  0
  7 12  1  0
 12 13  1  0
 12 11  2  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 10  1  0
 10  9  2  0
  7  6  1  0
 10 11  1  0
  9  8  1  0
 23 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
 27 43  1  1
 28 44  1  0
 13 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
  9 37  1  0
M  END


  Mrv1652309082204312D          

 28 31  0  0  1  0            999 V2000
    7.1953   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8363   -2.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3814    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  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
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0260367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC[C@@H]1[C@@H](O)OC2=C1C(O)=C1C(=O)C3=C(O)C=C(O)C=C3C(=O)C1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O8/c1-7(21)2-3-9-15-13(28-20(9)27)6-11-16(19(15)26)18(25)14-10(17(11)24)4-8(22)5-12(14)23/h4-6,9,20,22-23,26-27H,2-3H2,1H3/t9-,20-/m0/s1

> <INCHI_KEY>
JGXCLZAVTLWCBF-LXGOIASLSA-N

> <FORMULA>
C20H16O8

> <MOLECULAR_WEIGHT>
384.34

> <EXACT_MASS>
384.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.0247813431716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-2,4,6,8-tetrahydroxy-3-(3-oxobutyl)-2H,3H,5H,10H-anthra[2,3-b]furan-5,10-dione

> <JCHEM_LOGP>
2.9751465896666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.96720069827984

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.213338879529154

> <JCHEM_PKA_STRONGEST_BASIC>
-4.239822443825237

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
96.84169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2,4,6,8-tetrahydroxy-3-(3-oxobutyl)-2H,3H-anthra[2,3-b]furan-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      13.431  -4.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.925  -3.725   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.894  -4.870   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.449  -2.261   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.943  -1.941   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.467  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.467   2.016   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.372   0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.912   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   10   25                                                  
CONECT   25   24                                                            
CONECT   26    8   27                                                       
CONECT   27   26    6   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
1'-Hydroxyversicolorone	ChEBI

Chemical Formula

C₂₀H₁₆O₈

Average Mass

384.3400 Da

Monoisotopic Mass

384.08452 Da

IUPAC Name

(2S,3S)-2,4,6,8-tetrahydroxy-3-(3-oxobutyl)-2H,3H,5H,10H-anthra[2,3-b]furan-5,10-dione

Traditional Name

(2S,3S)-2,4,6,8-tetrahydroxy-3-(3-oxobutyl)-2H,3H-anthra[2,3-b]furan-5,10-dione

CAS Registry Number

Not Available

SMILES

CC(=O)CC[C@@H]1[C@@H](O)OC2=C1C(O)=C1C(=O)C3=C(O)C=C(O)C=C3C(=O)C1=C2

InChI Identifier

InChI=1S/C20H16O8/c1-7(21)2-3-9-15-13(28-20(9)27)6-11-16(19(15)26)18(25)14-10(17(11)24)4-8(22)5-12(14)23/h4-6,9,20,22-23,26-27H,2-3H2,1H3/t9-,20-/m0/s1

InChI Key

JGXCLZAVTLWCBF-LXGOIASLSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Naphthofuran
Coumaran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Hemiacetal
Organoheterocyclic compound
Polyol
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:71634 )
polyphenol (CHEBI:71634 )
lactol (CHEBI:71634 )
anthrafuran (CHEBI:71634 )

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	2.98	ChemAxon
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.84 m³·mol⁻¹	ChemAxon
Polarizability	38.02 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

Not Available

Chemspider ID

159450

KEGG Compound ID

C20503

BioCyc ID

CPD-10168

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

183380

PDB ID

Not Available

ChEBI ID

71634

Good Scents ID

Not Available

References

General References

Yabe K, Chihaya N, Hamamatsu S, Sakuno E, Hamasaki T, Nakajima H, Bennett JW: Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis. Appl Environ Microbiol. 2003 Jan;69(1):66-73. doi: 10.1128/AEM.69.1.66-73.2003. [PubMed:12513978 ]
Chang PK, Yabe K, Yu J: The Aspergillus parasiticus estA-encoded esterase converts versiconal hemiacetal acetate to versiconal and versiconol acetate to versiconol in aflatoxin biosynthesis. Appl Environ Microbiol. 2004 Jun;70(6):3593-9. doi: 10.1128/AEM.70.6.3593-3599.2004. [PubMed:15184162 ]
Wen Y, Hatabayashi H, Arai H, Kitamoto HK, Yabe K: Function of the cypX and moxY genes in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol. 2005 Jun;71(6):3192-8. doi: 10.1128/AEM.71.6.3192-3198.2005. [PubMed:15933021 ]
Shima Y, Shiina M, Shinozawa T, Ito Y, Nakajima H, Adachi Y, Yabe K: Participation in aflatoxin biosynthesis by a reductase enzyme encoded by vrdA gene outside the aflatoxin gene cluster. Fungal Genet Biol. 2009 Mar;46(3):221-31. doi: 10.1016/j.fgb.2008.12.005. Epub 2009 Jan 3. [PubMed:19211038 ]
Tolmie C, Smit MS, Opperman DJ: Alternative Splicing of the Aflatoxin-Associated Baeyer(-)Villiger Monooxygenase from Aspergillus flavus: Characterisation of MoxY Isoforms. Toxins (Basel). 2018 Dec 5;10(12):521. doi: 10.3390/toxins10120521. [PubMed:30563144 ]
Ehrlich KC: Predicted roles of the uncharacterized clustered genes in aflatoxin biosynthesis. Toxins (Basel). 2009 Sep;1(1):37-58. doi: 10.3390/toxins1010037. Epub 2009 Sep 25. [PubMed:22069531 ]
LOTUS database [Link]

Showing NP-Card for hydroxyversicolorone (NP0260367)

MOL for NP0260367 (hydroxyversicolorone)

3D MOL for NP0260367 (hydroxyversicolorone)

3D SDF for NP0260367 (hydroxyversicolorone)

3D-SDF for NP0260367 (hydroxyversicolorone)

PDB for NP0260367 (hydroxyversicolorone)

3D PDB for NP0260367 (hydroxyversicolorone)

SMILES for NP0260367 (hydroxyversicolorone)

INCHI for NP0260367 (hydroxyversicolorone)

Structure for NP0260367 (hydroxyversicolorone)

3D Structure for NP0260367 (hydroxyversicolorone)