NP-MRD: Showing NP-Card for Wortmin (NP0084463)

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Record Information

Version

2.0

Created at

2022-04-29 05:11:06 UTC

Updated at

2022-04-29 05:11:07 UTC

NP-MRD ID

NP0084463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wortmin

Description

Wortmin belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Wortmin is found in Penicillium wortmanni Kloecker, Penicillium wortmannii and Tessaracoccus wortmannii. Wortmin was first documented in 2016 (PMID: 27054912). Based on a literature review very few articles have been published on Wortmin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207112D          

 32 34  0  0  0  0            999 V2000
    0.0000    0.8250    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000   -1.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303   -2.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7428   -1.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4340    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.2813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   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
    2.1434   -0.4125    0.0000 O   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
    2.8579   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  2  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 24 32  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    6.8422    0.7179    2.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2120   -0.1222    1.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5576    0.3970    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444   -0.4795   -0.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9625    0.3079   -1.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571    0.3700   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -0.5682    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4026   -1.2919    1.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -1.6251    0.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9133   -0.8299    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -1.2903    1.5955 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247   -0.5217   -0.6535 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0940   -1.6338   -1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -0.4802   -0.1857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    0.4192    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9116    1.2089    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    0.4443    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0592   -0.4461    0.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -1.4297   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3693   -0.4407    1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7894    0.4482    2.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1339    0.4445    2.5369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0083   -0.4846    1.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    1.3224    2.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355    1.3283    2.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    2.2444    2.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860    0.7602   -1.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6259    0.5504   -2.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.1206   -3.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280    0.8937   -5.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.8684   -3.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    1.4213   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.7796    2.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    0.3911    3.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9438    0.5676    2.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3050   -1.2044    1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    1.4735    0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7426   -0.8242   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266   -0.1722   -2.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4066    1.3063   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219   -2.2067    1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8113   -0.6319    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432   -1.2662   -2.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5408   -2.4871   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732   -1.9179   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447   -2.1041   -0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1569    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -0.9439   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0984   -1.1280    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6469   -1.5160    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0949   -0.2499    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9950   -0.3919    2.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2231    2.0198    3.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171    2.5223    2.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    1.4423   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    1.3493   -5.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2051   -0.1779   -5.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    1.3991   -5.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    2.0102    0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691    2.1374   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 25 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 12 14  1  1
 12 13  1  0
 12 27  1  0
 27 32  1  0
 32  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  7 10  1  0
 10 11  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 10 12  1  0
  5  6  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 26 54  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 27 55  1  6
 32 59  1  0
 32 60  1  0
  8 41  1  0
  8 42  1  0
  4 38  1  6
  5 39  1  0
  5 40  1  0
  3 37  1  0
  2 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
M  END


  Mrv1652304292207112D          

 32 34  0  0  0  0            999 V2000
    0.0000    0.8250    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000   -1.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303   -2.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7428   -1.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4340    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    1.2813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -0.5558    0.0000 C   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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   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
    2.1434   -0.4125    0.0000 O   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
    2.8579   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  2  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 24 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)OC2(C)C(CC3=C(COC(C3)\C=C\C)C2=O)OC(C)=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O8/c1-6-7-16-9-15-10-20(31-14(3)25)24(4,22(27)18(15)12-30-16)32-23(28)21-13(2)8-17(29-5)11-19(21)26/h6-8,11,16,20,26H,9-10,12H2,1-5H3/b7-6+

> <INCHI_KEY>
AVHDFUVJYKFWOO-VOTSOKGWSA-N

> <FORMULA>
C24H28O8

> <MOLECULAR_WEIGHT>
444.48

> <EXACT_MASS>
444.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.76576475003458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(acetyloxy)-7-methyl-8-oxo-3-[(1E)-prop-1-en-1-yl]-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-7-yl 2-hydroxy-4-methoxy-6-methylbenzoate

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
4.316810286666666

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.753621572200666

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0547677923567464

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000003

> <JCHEM_REFRACTIVITY>
117.30629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(acetyloxy)-7-methyl-8-oxo-3-[(1E)-prop-1-en-1-yl]-3,4,5,6-tetrahydro-1H-2-benzopyran-7-yl 2-hydroxy-4-methoxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.860   0.677   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.377   0.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.367  -0.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.840  -1.682   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.324  -1.950   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.830  -2.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.347  -2.595   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.337  -3.774   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.853  -3.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.873  -1.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.883   0.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.410   1.479   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.904   2.392   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.850  -1.037   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   17   18                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14                                                            
CONECT   16    5                                                            
CONECT   17    3                                                            
CONECT   18    3   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24    2   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₈

Average Mass

444.4800 Da

Monoisotopic Mass

444.17842 Da

IUPAC Name

6-(acetyloxy)-7-methyl-8-oxo-3-[(1E)-prop-1-en-1-yl]-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-7-yl 2-hydroxy-4-methoxy-6-methylbenzoate

Traditional Name

6-(acetyloxy)-7-methyl-8-oxo-3-[(1E)-prop-1-en-1-yl]-3,4,5,6-tetrahydro-1H-2-benzopyran-7-yl 2-hydroxy-4-methoxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)OC2(C)C(CC3=C(COC(C3)\C=C\C)C2=O)OC(C)=O)C(C)=C1

InChI Identifier

InChI=1S/C24H28O8/c1-6-7-16-9-15-10-20(31-14(3)25)24(4,22(27)18(15)12-30-16)32-23(28)21-13(2)8-17(29-5)11-19(21)26/h6-8,11,16,20,26H,9-10,12H2,1-5H3/b7-6+

InChI Key

AVHDFUVJYKFWOO-VOTSOKGWSA-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
Penicillium wortmanni Kloecker	Fungi	KNApSAcK
Talaromyces wortmannii	Fungi	KNApSAcK
Tessaracoccus wortmannii	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Salicylic acid or derivatives
Methoxyphenol
Benzopyran
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
M-cresol
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Toluene
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.25	ALOGPS
logP	4.32	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.31 m³·mol⁻¹	ChemAxon
Polarizability	45.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053895

Chemspider ID

26285801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90472454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Buttachon S, May Zin WW, Dethoup T, Gales L, Pereira JA, Silva AM, Kijjoa A: Secondary Metabolites from the Culture of the Marine Sponge-Associated Fungi Talaromyces tratensis and Sporidesmium circinophorum. Planta Med. 2016 Jun;82(9-10):888-96. doi: 10.1055/s-0042-103687. Epub 2016 Apr 7. [PubMed:27054912 ]

Showing NP-Card for Wortmin (NP0084463)

MOL for NP0084463 (Wortmin)

3D MOL for NP0084463 (Wortmin)

3D SDF for NP0084463 (Wortmin)

3D-SDF for NP0084463 (Wortmin)

PDB for NP0084463 (Wortmin)

3D PDB for NP0084463 (Wortmin)

SMILES for NP0084463 (Wortmin)

INCHI for NP0084463 (Wortmin)

Structure for NP0084463 (Wortmin)

3D Structure for NP0084463 (Wortmin)