NP-MRD: Showing NP-Card for penisimplicissin (NP0036530)

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Record Information

Version

2.0

Created at

2021-06-20 19:40:47 UTC

Updated at

2021-06-30 00:08:13 UTC

NP-MRD ID

NP0036530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

penisimplicissin

Provided By

JEOL Database JEOL Logo

Description

penisimplicissin is found in Penicillium rubrum and Talaromyces thailandiasis. penisimplicissin was first documented in 2012 (Stierle, A. A., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121403D          

 36 38  0  0  0  0            999 V2000
   -4.1394   -3.7349    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -3.7128    2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -2.6190    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -2.6469    1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -1.6025    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.5350    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5618    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.5367    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -0.5198    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -1.5361    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    0.6998    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    1.0266    0.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3894   -0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899    0.7117   -0.3628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122    0.5071   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.1975   -2.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.0165   -4.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1520   -4.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.0937   -5.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881    0.4819   -3.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    0.7169   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.0864   -1.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791   -3.7373    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -2.8999    3.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -4.6633    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -3.5130    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.5327    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -2.3278    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -2.5960    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.4557    1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.3565    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    0.0475   -2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -1.1120   -6.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    0.6085   -6.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    0.0267   -6.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6014   -3.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3 10  2  0  0  0  0
 11 12  2  0  0  0  0
 10  9  1  0  0  0  0
 14 15  1  0  0  0  0
 15 21  1  0  0  0  0
  4  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 21 20  1  0  0  0  0
 20 18  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 14  8  1  0  0  0  0
 21 22  2  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  1  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
 20 36  1  0  0  0  0
 16 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.1394   -3.7349    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -3.7128    2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -2.6190    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -2.6469    1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -1.6025    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.5350    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5618    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.5367    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -0.5198    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -1.5361    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    0.6998    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    1.0266    0.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3894   -0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899    0.7117   -0.3628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122    0.5071   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.1975   -2.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.0165   -4.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1520   -4.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.0937   -5.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881    0.4819   -3.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    0.7169   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.0864   -1.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791   -3.7373    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -2.8999    3.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -4.6633    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -3.5130    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.5327    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -2.3278    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -2.5960    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.4557    1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.3565    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    0.0475   -2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -1.1120   -6.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    0.6085   -6.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    0.0267   -6.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6014   -3.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  5  6  1  0
  6  7  1  0
  3 10  2  0
 11 12  2  0
 10  9  1  0
 14 15  1  0
 15 21  1  0
  4  3  1  0
  8  5  1  0
  9 11  1  0
 11 13  1  0
 13 14  1  0
 15 16  2  0
 21 20  1  0
 20 18  2  0
 18 17  1  0
 17 16  1  0
 14  8  1  0
 21 22  2  0
  5  4  2  0
  2  1  1  0
  3  2  1  0
 18 19  1  0
  4 26  1  0
 10 30  1  0
 14 31  1  1
  7 27  1  0
  7 28  1  0
  7 29  1  0
 20 36  1  0
 16 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv1652306202121403D          

 36 38  0  0  0  0            999 V2000
   -4.1394   -3.7349    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -3.7128    2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -2.6190    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -2.6469    1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -1.6025    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.5350    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5618    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.5367    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -0.5198    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -1.5361    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    0.6998    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    1.0266    0.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3894   -0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899    0.7117   -0.3628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122    0.5071   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.1975   -2.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.0165   -4.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1520   -4.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.0937   -5.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881    0.4819   -3.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    0.7169   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.0864   -1.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791   -3.7373    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -2.8999    3.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -4.6633    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -3.5130    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.5327    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -2.3278    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -2.5960    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.4557    1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.3565    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    0.0475   -2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -1.1120   -6.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    0.6085   -6.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    0.0267   -6.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6014   -3.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3 10  2  0  0  0  0
 11 12  2  0  0  0  0
 10  9  1  0  0  0  0
 14 15  1  0  0  0  0
 15 21  1  0  0  0  0
  4  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 21 20  1  0  0  0  0
 20 18  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  1  0  0  0  0
 14  8  1  0  0  0  0
 21 22  2  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  1  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
 20 36  1  0  0  0  0
 16 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C(=O)C([H])=C(O1)C([H])([H])[H])[C@@]1([H])OC(=O)C2=C1C(OC([H])([H])[H])=C([H])C(OC([H])([H])[H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-8-4-12(17)11(7-21-8)15-14-10(16(18)22-15)5-9(19-2)6-13(14)20-3/h4-7,15H,1-3H3/t15-/m1/s1

> <INCHI_KEY>
FKFNGBPZNWNWSG-OAHLLOKOSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.060541836371193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-4,6-dimethoxy-3-(6-methyl-4-oxo-4H-pyran-3-yl)-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.6989832886666667

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.466263705334361

> <JCHEM_PKA_STRONGEST_BASIC>
-4.473726337468095

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
78.8596

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penisimplicissin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.1394   -3.7349    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -3.7128    2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -2.6190    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -2.6469    1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -1.6025    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.5350    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5618    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.5367    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -0.5198    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -1.5361    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    0.6998    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    1.0266    0.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3894   -0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899    0.7117   -0.3628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122    0.5071   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.1975   -2.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.0165   -4.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1520   -4.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.0937   -5.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881    0.4819   -3.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    0.7169   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.0864   -1.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791   -3.7373    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -2.8999    3.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -4.6633    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -3.5130    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.5327    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -2.3278    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -2.5960    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.4557    1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.3565    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    0.0475   -2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -1.1120   -6.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    0.6085   -6.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    0.0267   -6.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6014   -3.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  5  6  1  0
  6  7  1  0
  3 10  2  0
 11 12  2  0
 10  9  1  0
 14 15  1  0
 15 21  1  0
  4  3  1  0
  8  5  1  0
  9 11  1  0
 11 13  1  0
 13 14  1  0
 15 16  2  0
 21 20  1  0
 20 18  2  0
 18 17  1  0
 17 16  1  0
 14  8  1  0
 21 22  2  0
  5  4  2  0
  2  1  1  0
  3  2  1  0
 18 19  1  0
  4 26  1  0
 10 30  1  0
 14 31  1  1
  7 27  1  0
  7 28  1  0
  7 29  1  0
 20 36  1  0
 16 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.139  -3.735   3.213  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.814  -3.713   2.694  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.458  -2.619   1.952  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.131  -2.647   1.474  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.610  -1.603   0.699  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.651  -1.535   0.192  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.562  -2.562   0.567  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.444  -0.537   0.406  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.738  -0.520   0.885  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.280  -1.536   1.655  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.392   0.700   0.441  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.538   1.027   0.672  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.478   1.389  -0.298  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.190   0.712  -0.363  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.812   0.507  -1.797  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.651   0.198  -2.798  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.293   0.017  -4.112  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.042   0.152  -4.456  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.328  -0.094  -5.902  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.988   0.482  -3.567  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.610   0.717  -2.159  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.451   1.086  -1.349  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.879  -3.737   2.406  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.307  -2.900   3.902  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.261  -4.663   3.779  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.527  -3.513   1.730  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.239  -3.533   0.177  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.532  -2.328   0.118  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.695  -2.596   1.653  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.306  -1.456   1.992  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.484   1.357   0.172  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.716   0.048  -2.677  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.036  -1.112  -6.178  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.236   0.609  -6.524  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.391   0.027  -6.137  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.033   0.601  -3.820  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3                                                       
CONECT    3   10    4    2                                                  
CONECT    4    3    5   26                                                  
CONECT    5    6    8    4                                                  
CONECT    6    5    7                                                       
CONECT    7    6   27   28   29                                             
CONECT    8    9    5   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    3    9   30                                                  
CONECT   11   12    9   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   15   13    8   31                                             
CONECT   15   14   21   16                                                  
CONECT   16   15   17   32                                                  
CONECT   17   18   16                                                       
CONECT   18   20   17   19                                                  
CONECT   19   18   33   34   35                                             
CONECT   20   21   18   36                                                  
CONECT   21   15   20   22                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30   10                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   19                                                            
CONECT   34   19                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -4.1394   -3.7349    3.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -3.7128    2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577   -2.6190    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -2.6469    1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -1.6025    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.5350    0.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -2.5618    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440   -0.5367    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379   -0.5198    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -1.5361    1.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3919    0.6998    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381    1.0266    0.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    1.3894   -0.2979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899    0.7117   -0.3628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122    0.5071   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    0.1975   -2.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.0165   -4.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1520   -4.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -0.0937   -5.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881    0.4819   -3.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    0.7169   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.0864   -1.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791   -3.7373    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -2.8999    3.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607   -4.6633    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267   -3.5130    1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.5327    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -2.3278    0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -2.5960    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.4557    1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    1.3565    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    0.0475   -2.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358   -1.1120   -6.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    0.6085   -6.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    0.0267   -6.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6014   -3.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  5  6  1  0
  6  7  1  0
  3 10  2  0
 11 12  2  0
 10  9  1  0
 14 15  1  0
 15 21  1  0
  4  3  1  0
  8  5  1  0
  9 11  1  0
 11 13  1  0
 13 14  1  0
 15 16  2  0
 21 20  1  0
 20 18  2  0
 18 17  1  0
 17 16  1  0
 14  8  1  0
 21 22  2  0
  5  4  2  0
  2  1  1  0
  3  2  1  0
 18 19  1  0
  4 26  1  0
 10 30  1  0
 14 31  1  1
  7 27  1  0
  7 28  1  0
  7 29  1  0
 20 36  1  0
 16 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

(3S)-4,6-dimethoxy-3-(6-methyl-4-oxo-4H-pyran-3-yl)-1,3-dihydro-2-benzofuran-1-one

Traditional Name

penisimplicissin

CAS Registry Number

Not Available

SMILES

[H]C1=C(C(=O)C([H])=C(O1)C([H])([H])[H])[C@@]1([H])OC(=O)C2=C1C(OC([H])([H])[H])=C([H])C(OC([H])([H])[H])=C2[H]

InChI Identifier

InChI=1S/C16H14O6/c1-8-4-12(17)11(7-21-8)15-14-10(16(18)22-15)5-9(19-2)6-13(14)20-3/h4-7,15H,1-3H3/t15-/m1/s1

InChI Key

FKFNGBPZNWNWSG-OAHLLOKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Talaromyces ruber	JEOL database	Stierle, A. A., et al, J. Nat. Prod. 75, 344 (2012)
Talaromyces thailandiasis	Fungi	KNApSAcK

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.87	ALOGPS
logP	1.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.86 m³·mol⁻¹	ChemAxon
Polarizability	30.06 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	No	ChemAxon

External Links

Not Available

References

General References

Stierle, A. A., et al. (2012). Stierle, A. A., et al, J. Nat. Prod. 75, 344 (2012). J. Nat. Prod..

Showing NP-Card for penisimplicissin (NP0036530)

MOL for NP0036530 (penisimplicissin)

3D MOL for NP0036530 (penisimplicissin)

3D SDF for NP0036530 (penisimplicissin)

3D-SDF for NP0036530 (penisimplicissin)

PDB for NP0036530 (penisimplicissin)

3D PDB for NP0036530 (penisimplicissin)

SMILES for NP0036530 (penisimplicissin)

INCHI for NP0036530 (penisimplicissin)

Structure for NP0036530 (penisimplicissin)

3D Structure for NP0036530 (penisimplicissin)