NP-MRD: Showing NP-Card for Penstyrylpyrone (NP0011736)

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Record Information

Version

2.0

Created at

2021-01-05 21:20:03 UTC

Updated at

2021-07-15 17:09:47 UTC

NP-MRD ID

NP0011736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penstyrylpyrone

Provided By

NPAtlas

Description

4-Methoxy-3-methyl-6-[(E)-2-phenylethenyl]-2H-pyran-2-one belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Penstyrylpyrone is found in Penicillium. Penstyrylpyrone was first documented in 2013 (PMID: 23612372). Based on a literature review very few articles have been published on 4-methoxy-3-methyl-6-[(E)-2-phenylethenyl]-2H-pyran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116583D          

 32 33  0  0  0  0            999 V2000
   -3.2109    2.0219   -1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.8013   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.1668   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0206   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.9773    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7888    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.2889   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    0.4028   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -0.5488    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0461   -0.3581    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    0.8150    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.7996   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    1.5937   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.1226    0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -2.3561    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -3.4488    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -1.3844    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.6302    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    2.5825   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.6999   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    1.8652   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9834   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.6177    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783    1.1158   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.4995    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -1.1633    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793    1.0016    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245    2.7185   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.3849   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748   -0.8610    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.5474   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066   -2.6248    0.4348 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17  3  2  0  0  0  0
 13  8  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 18 30  1  0  0  0  0
 18 31  1  0  0  0  0
 18 32  1  0  0  0  0
M  END

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.2109    2.0219   -1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.8013   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.1668   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0206   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.9773    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7888    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.2889   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    0.4028   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -0.5488    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0461   -0.3581    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    0.8150    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.7996   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    1.5937   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.1226    0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -2.3561    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -3.4488    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -1.3844    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.6302    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    2.5825   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.6999   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    1.8652   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9834   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.6177    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783    1.1158   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.4995    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -1.1633    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793    1.0016    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245    2.7185   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.3849   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748   -0.8610    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.5474   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066   -2.6248    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17  3  2  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END


  Mrv1652306242116583D          

 32 33  0  0  0  0            999 V2000
   -3.2109    2.0219   -1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.8013   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.1668   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0206   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.9773    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7888    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.2889   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    0.4028   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -0.5488    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0461   -0.3581    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    0.8150    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.7996   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    1.5937   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.1226    0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -2.3561    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -3.4488    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -1.3844    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.6302    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    2.5825   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.6999   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    1.8652   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9834   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.6177    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783    1.1158   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.4995    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -1.1633    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793    1.0016    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245    2.7185   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.3849   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748   -0.8610    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.5474   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066   -2.6248    0.4348 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
  3  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17  3  2  0  0  0  0
 13  8  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 18 30  1  0  0  0  0
 18 31  1  0  0  0  0
 18 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011736

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-11-14(17-2)10-13(18-15(11)16)9-8-12-6-4-3-5-7-12/h3-10H,1-2H3/b9-8+

> <INCHI_KEY>
ALTYBKZUBTXQOK-CMDGGOBGSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.784033744043754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-3-methyl-6-[(E)-2-phenylethenyl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.035040364333333

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.83492300756427

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
73.09780000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-3-methyl-6-[(E)-2-phenylethenyl]pyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.2109    2.0219   -1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.8013   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.1668   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0206   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.9773    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7888    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.2889   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    0.4028   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -0.5488    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0461   -0.3581    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    0.8150    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.7996   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    1.5937   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.1226    0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -2.3561    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3687   -1.3844    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.6302    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    2.5825   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.6999   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    1.8652   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9834   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.6177    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783    1.1158   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.4995    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -1.1633    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793    1.0016    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245    2.7185   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.3849   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748   -0.8610    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.5474   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066   -2.6248    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17  3  2  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  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      -3.211   2.022  -1.283  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.771   0.801  -0.836  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.901  -0.167  -0.360  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.512   0.021  -0.310  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.702  -0.977   0.172  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.743  -0.789   0.228  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.355   0.289  -0.156  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.797   0.403  -0.071  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.662  -0.549   0.397  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.046  -0.358   0.446  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.592   0.815   0.017  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.754   1.800  -0.462  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.396   1.594  -0.502  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.243  -2.123   0.591  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.517  -2.356   0.569  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.974  -3.449   0.974  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.369  -1.384   0.094  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.816  -1.630   0.062  0.00  0.00           C+0
HETATM   19  H   UNK     0      -2.737   2.583  -0.436  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.979   2.700  -1.710  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.397   1.865  -2.031  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.158   0.983  -0.670  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.310  -1.618   0.618  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.778   1.116  -0.547  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.254  -1.500   0.748  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.656  -1.163   0.831  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.679   1.002   0.041  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.224   2.719  -0.794  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.762   2.385  -0.883  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.375  -0.861   0.662  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.238  -1.547  -0.970  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.107  -2.625   0.435  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12    8   29                                                  
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18    3                                                  
CONECT   18   17   30   31   32                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   18                                                            
CONECT   31   18                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
   -3.2109    2.0219   -1.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7706    0.8013   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007   -0.1668   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    0.0206   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -0.9773    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7888    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545    0.2889   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    0.4028   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -0.5488    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0461   -0.3581    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    0.8150    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.7996   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    1.5937   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.1226    0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -2.3561    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -3.4488    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687   -1.3844    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.6302    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    2.5825   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    2.6999   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3971    1.8652   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9834   -0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.6177    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783    1.1158   -0.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536   -1.4995    0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -1.1633    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6793    1.0016    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245    2.7185   -0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.3849   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748   -0.8610    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384   -1.5474   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1066   -2.6248    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17  3  2  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

4-methoxy-3-methyl-6-[(E)-2-phenylethenyl]-2H-pyran-2-one

Traditional Name

4-methoxy-3-methyl-6-[(E)-2-phenylethenyl]pyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)OC(\C=C\C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C15H14O3/c1-11-14(17-2)10-13(18-15(11)16)9-8-12-6-4-3-5-7-12/h3-10H,1-2H3/b9-8+

InChI Key

ALTYBKZUBTXQOK-CMDGGOBGSA-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	NPAtlas	23612372

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Styrene
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	3.49	ALOGPS
logP	3.04	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.1 m³·mol⁻¹	ChemAxon
Polarizability	26.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002690

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29215665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132602092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee DS, Jang JH, Ko W, Kim KS, Sohn JH, Kang MS, Ahn JS, Kim YC, Oh H: PTP1B inhibitory and anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungus Penicillium sp. JF-55. Mar Drugs. 2013 Apr 23;11(4):1409-26. doi: 10.3390/md11041409. [PubMed:23612372 ]

Showing NP-Card for Penstyrylpyrone (NP0011736)

MOL for NP0011736 (Penstyrylpyrone)

3D MOL for NP0011736 (Penstyrylpyrone)

3D SDF for NP0011736 (Penstyrylpyrone)

3D-SDF for NP0011736 (Penstyrylpyrone)

PDB for NP0011736 (Penstyrylpyrone)

3D PDB for NP0011736 (Penstyrylpyrone)

SMILES for NP0011736 (Penstyrylpyrone)

INCHI for NP0011736 (Penstyrylpyrone)

Structure for NP0011736 (Penstyrylpyrone)

3D Structure for NP0011736 (Penstyrylpyrone)