NP-MRD: Showing NP-Card for 6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one (NP0251957)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 15:18:57 UTC

Updated at

2022-09-07 15:18:57 UTC

NP-MRD ID

NP0251957

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one

Description

Citreoviridin A belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. As a result it has been shown to inhibit mitochondrial energy-linked reactions such as ADP-stimulated respiration, ATP-driven reduction of NAD + by succinate, and ATP-driven NAD transhydrogenase. Citreoviridin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Citreoviridin A is a potentially toxic compound. It is isolated from mouldy rice. Citreoviridin A belongs to the family of Pyranones and Derivatives. They can also inhibit uptake of anions and cations by these transporters, interfering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. Citreoviridin A is a metabolite of Penicillium citreo-viride, Penicillium toxicarium, Penicillium ochrosalmoneum and Aspergillus terreus. Citreoviridin inhibits both membrane-bound and soluble mitochondrial ATPases. 6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one is found in Aspergillus aureoterreus, Penicillium aurantiacobrunneum, Penicillium citreonigrum, Penicillium miczynskii and Penicillium simplicissimum. This can cause central nervous system depression leading to respiratory and cardiovascular failures and death.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09061400422D          

 36 37  0  0  0  0            999 V2000
    5.3693    2.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7290   -2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5688    4.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5689   -3.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -0.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5418    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092    0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2216   -1.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4803   -4.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904    2.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1230    1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0615   -3.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7841    3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3078   -2.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -3.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7266   -4.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    2.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167    4.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592   -4.5349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    4.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6687    4.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9014   -4.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6404   -3.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292    2.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9606   -0.9174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0491   -0.2831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7881    0.7236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8005   -2.0734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629    0.5374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8890   -1.4391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5441    1.8428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16  2  1  0  0  0  0
 17  3  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 13  1  0  0  0  0
 22  4  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23  5  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  1  0  0  0  0
 24 20  2  0  0  0  0
 25 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  6  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 28 20  1  0  0  0  0
 29 17  1  0  0  0  0
 29 22  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32  9  1  0  0  0  0
 33 10  1  0  0  0  0
 34 11  1  0  0  0  0
 35 12  1  0  0  0  0
 36 14  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
   10.4494    0.5270   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0588    0.6410   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3440   -0.5063   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9387   -1.7363   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1807   -2.8458    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7118   -3.9713    0.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9213   -2.7047    0.3376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2389   -1.5524    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294   -1.6545    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8575   -0.8194    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -1.1285    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -0.2774    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -0.6028    0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976    0.2501    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2965   -0.0869    0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526   -1.3915    1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2518    0.7877    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6987    0.6085    0.7419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0383    0.0942    2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2332    1.9162    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5556    1.8107    0.4024 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8758    2.8604   -0.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8587    0.4573   -0.1268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5896    0.4760   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5630   -0.3195    0.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439   -0.1019   -0.3444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0428    0.3436   -1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9480   -0.4360   -0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3502    0.9164   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    0.3159    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7906    1.5347   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6473   -0.2578   -1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0211   -1.7935   -0.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4408   -2.6212    0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873    0.1167   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -2.0860    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297    0.6876   -0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.5574    1.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.1996   -0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617   -2.2286    0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -1.4973    2.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6960   -1.6652    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726    1.7406    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848   -0.8348    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1617   -0.0295    2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7046    0.8041    2.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1918    2.0263    1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6237    2.4771   -1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9512    3.1137   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2249    3.7632   -0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3996    1.2232   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0922   -0.5281   -1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8958    0.5557   -2.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0750    0.3154    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5487   -1.1749   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285    0.8860   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8734    1.1381   -1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6947    1.1732    0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2210    1.6492    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8 28  2  0
 28 29  1  0
 28  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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 18 17  1  6
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  1
 23 26  1  0
 26 27  1  0
  7  8  1  0
 26 18  1  0
 12 37  1  0
 11 36  1  0
 10 35  1  0
  9 34  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  6
 27 56  1  0
M  END


  Mrv0541 09061400422D          

 36 37  0  0  0  0            999 V2000
    5.3693    2.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7290   -2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5688    4.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5689   -3.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6280   -0.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5418    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4679   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2092    0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2216   -1.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4803   -4.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904    2.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1230    1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0615   -3.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7841    3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3078   -2.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1478   -3.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7266   -4.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    2.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167    4.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592   -4.5349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    4.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6687    4.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9014   -4.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6404   -3.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292    2.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9606   -0.9174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0491   -0.2831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7881    0.7236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8005   -2.0734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629    0.5374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8890   -1.4391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5441    1.8428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16  2  1  0  0  0  0
 17  3  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20 13  1  0  0  0  0
 22  4  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23  5  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  1  0  0  0  0
 24 20  2  0  0  0  0
 25 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  6  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 28 20  1  0  0  0  0
 29 17  1  0  0  0  0
 29 22  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32  9  1  0  0  0  0
 33 10  1  0  0  0  0
 34 11  1  0  0  0  0
 35 12  1  0  0  0  0
 36 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251957

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])/C(/C)=C(\[H])C1(C)OC(C)C(C)(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+

> <INCHI_KEY>
JLSVDPQAIKFBTO-USJRQALFSA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.4807

> <EXACT_MASS>
402.204238692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.46314193988334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
2.4590114166666655

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.027781536676851

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.600983692839542

> <JCHEM_PKA_STRONGEST_BASIC>
-3.662280515270547

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
118.01279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0      10.023   3.787   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.294  -4.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.995   7.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.008   5.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.254   9.112   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.862  -7.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.506  -0.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.912  -1.434   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.345   0.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.073  -2.965   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.591   1.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.480  -3.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.963  -8.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.675   4.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.430   3.161   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.048  -5.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.530   7.062   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.641  -5.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.209  -7.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.556  -7.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.039   7.062   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.514   5.598   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.284   7.968   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.311  -8.465   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.574   7.538   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      14.315   9.112   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      16.616  -7.907   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.395  -6.028   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.054   5.598   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       9.260  -1.712   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      13.158  -0.528   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.938   1.351   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      10.828  -3.870   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      12.997   1.003   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      14.726  -2.686   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      14.082   3.440   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   27                                                            
CONECT    7    8    9   30                                                  
CONECT    8    7   10   31                                                  
CONECT    9    7   11   32                                                  
CONECT   10    8   12   33                                                  
CONECT   11    9   15   34                                                  
CONECT   12   10   18   35                                                  
CONECT   13   19   20                                                       
CONECT   14   15   22   36                                                  
CONECT   15    1   11   14                                                  
CONECT   16    2   18   19                                                  
CONECT   17    3   23   29                                                  
CONECT   18   12   16   28                                                  
CONECT   19   13   16   27                                                  
CONECT   20   13   24   28                                                  
CONECT   21   22   23   25                                                  
CONECT   22    4   14   21   29                                             
CONECT   23    5   17   21   26                                             
CONECT   24   20                                                            
CONECT   25   21                                                            
CONECT   26   23                                                            
CONECT   27    6   19                                                       
CONECT   28   18   20                                                       
CONECT   29   17   22                                                       
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₆

Average Mass

402.4807 Da

Monoisotopic Mass

402.20424 Da

IUPAC Name

6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one

Traditional Name

6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])/C(/C)=C(\[H])C1(C)OC(C)C(C)(O)C1O

InChI Identifier

InChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+

InChI Key

JLSVDPQAIKFBTO-USJRQALFSA-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

Species Name	Source	Reference
Aspergillus aureoterreus	LOTUS Database	35616633
Penicillium aurantiacobrunneum	LOTUS Database	35616633
Penicillium citreonigrum	LOTUS Database	35616633
Penicillium miczynskii	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Heteroaromatic compound
Vinylogous ester
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Lactone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.89	ALOGPS
logP	2.46	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.01 m³·mol⁻¹	ChemAxon
Polarizability	45.46 Å³	ChemAxon
Number of Rings	2	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5375783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one (NP0251957)

MOL for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

3D MOL for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

3D SDF for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

3D-SDF for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

PDB for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

3D PDB for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

SMILES for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

INCHI for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

Structure for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)

3D Structure for NP0251957 (6-[(1e,3e,5e,7e)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one)