NP-MRD: Showing NP-Card for Penilactone (NP0043943)

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Record Information

Version

1.0

Created at

2021-06-22 17:42:02 UTC

Updated at

2021-06-22 17:42:02 UTC

NP-MRD ID

NP0043943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penilactone

Description

Penilactone is found in Limonium tubiflorum. It was first documented in 2011 (PMID: 21146414).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043943
     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.8972    1.5978    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    0.3290    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0672   -0.8660    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624   -1.0751    1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3309    1.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -3.3077    2.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186   -2.6191    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611   -2.4634   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689   -1.2434   -1.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.4725   -3.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.1100   -0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    1.2378   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    2.1643   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    1.8164    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7955    2.6979    1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.4605    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -0.4526    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -1.8257    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644    1.8731   -2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.9918   -2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    1.1308   -3.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.2187   -1.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    1.5633    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    2.4962    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    1.5573    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2709    0.3913   -0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -0.6639    1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -1.7796    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.2328    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -1.1136    2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -3.6551    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -3.3791   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155   -2.4378   -1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.2482   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426    2.4824    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    0.1009    1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    2.8904   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    1.7801   -3.1141 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  2  1  0
 18  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
M  END


  Mrv1652306222119422D          

 22 24  0  0  1  0            999 V2000
    7.1096    1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4264    1.0341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7245    0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1090   -1.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5510   -1.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603   -1.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701   -1.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427    1.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7902    2.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    0.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    0.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -0.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5356   -0.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099   -0.9772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC(=O)C2CC(=O)C3=C(CC(=O)O1)C=C(O)C=C3O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-8-2-3-11(18)13-7-12(19)16-9(5-15(20)21-8)4-10(17)6-14(16)22-13/h4,6,8,13,17H,2-3,5,7H2,1H3/t8-,13?/m0/s1

> <INCHI_KEY>
FVRXJARCVLXBHQ-OADYLZGLSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.182811314786584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-3-hydroxy-9-methyl-8,17-dioxatricyclo[11.3.1.0^{5,16}]heptadeca-1,3,5(16)-triene-7,12,15-trione

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.4547839590000002

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.03867368848491

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.714074828905526

> <JCHEM_PKA_STRONGEST_BASIC>
-4.952481485836151

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
75.81700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-3-hydroxy-9-methyl-8,17-dioxatricyclo[11.3.1.0^{5,16}]heptadeca-1,3,5(16)-triene-7,12,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043943
     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.8972    1.5978    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    0.3290    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0672   -0.8660    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624   -1.0751    1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3309    1.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -3.3077    2.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186   -2.6191    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611   -2.4634   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689   -1.2434   -1.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.4725   -3.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.1100   -0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    1.2378   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    2.1643   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    1.8164    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7955    2.6979    1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.4605    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -0.4526    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -1.8257    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644    1.8731   -2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.9918   -2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    1.1308   -3.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.2187   -1.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    1.5633    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    2.4962    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    1.5573    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2709    0.3913   -0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -0.6639    1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -1.7796    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.2328    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -1.1136    2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -3.6551    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -3.3791   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155   -2.4378   -1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.2482   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426    2.4824    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    0.1009    1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    2.8904   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    1.7801   -3.1141 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  2  1  0
 18  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      13.271   2.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.996   1.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.552   0.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.416  -1.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.404  -2.271   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.228  -3.571   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.819  -2.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.637  -3.708   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.539  -2.569   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.104  -3.130   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.579  -0.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.316   0.852   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.106   2.229   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.340   3.227   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.942   4.714   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.861   2.987   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.901   1.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.827   0.489   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.339   0.883   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.210  -1.026   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.600  -1.820   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.418  -1.824   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2                                                       
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   11   22                                                  
CONECT   22   21    7                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    NP0043943
HETATM    1  C1  UNL     1       1.897   1.598   0.804  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.144   0.329   0.017  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.067  -0.866   0.947  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.762  -1.075   1.628  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.082  -2.331   1.293  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.429  -3.308   2.001  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.919  -2.619   0.281  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.261  -2.463  -1.064  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.769  -1.243  -1.761  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.747  -1.473  -3.016  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.175  -0.110  -0.992  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.987   1.238  -1.120  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.505   2.164  -0.245  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.257   1.816   0.845  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.796   2.698   1.736  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.455   0.460   1.010  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.938  -0.453   0.143  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.125  -1.826   0.308  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.064   1.873  -2.152  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.178   0.992  -2.218  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.775   1.131  -3.330  1.00  0.00           O  
HETATM   22  O6  UNL     1       1.486   0.219  -1.174  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.599   1.563   1.686  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.093   2.496   0.209  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.886   1.557   1.235  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.271   0.391  -0.217  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.901  -0.664   1.717  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.426  -1.780   0.450  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.080  -0.233   1.567  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.020  -1.114   2.752  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.265  -3.655   0.380  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.525  -3.379  -1.675  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.815  -2.438  -1.000  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.322   3.248  -0.411  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.343   2.482   2.533  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.055   0.101   1.861  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.195   2.890  -1.911  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.598   1.780  -3.114  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    6    7
CONECT    7    8   18   31
CONECT    8    9   32   33
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   19
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35
CONECT   16   17   17   36
CONECT   17   18
CONECT   19   20   37   38
CONECT   20   21   21   22
END

NP0043943
     RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
    1.8972    1.5978    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    0.3290    0.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0672   -0.8660    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624   -1.0751    1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0824   -2.3309    1.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -3.3077    2.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186   -2.6191    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611   -2.4634   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689   -1.2434   -1.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468   -1.4725   -3.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.1100   -0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    1.2378   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055    2.1643   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    1.8164    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7955    2.6979    1.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.4605    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380   -0.4526    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -1.8257    0.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0644    1.8731   -2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1777    0.9918   -2.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    1.1308   -3.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.2187   -1.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    1.5633    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    2.4962    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8856    1.5573    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2709    0.3913   -0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006   -0.6639    1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -1.7796    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.2328    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197   -1.1136    2.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2653   -3.6551    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -3.3791   -1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155   -2.4378   -1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.2482   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426    2.4824    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    0.1009    1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    2.8904   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    1.7801   -3.1141 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  2  1  0
 18  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

(9S)-3-hydroxy-9-methyl-8,17-dioxatricyclo[11.3.1.0^{5,16}]heptadeca-1,3,5(16)-triene-7,12,15-trione

Traditional Name

(9S)-3-hydroxy-9-methyl-8,17-dioxatricyclo[11.3.1.0^{5,16}]heptadeca-1,3,5(16)-triene-7,12,15-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC(=O)C2CC(=O)C3=C(CC(=O)O1)C=C(O)C=C3O2

InChI Identifier

InChI=1S/C16H16O6/c1-8-2-3-11(18)13-7-12(19)16-9(5-15(20)21-8)4-10(17)6-14(16)22-13/h4,6,8,13,17H,2-3,5,7H2,1H3/t8-,13?/m0/s1

InChI Key

FVRXJARCVLXBHQ-OADYLZGLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Limonium tubiflorum	Linigton's dataset	21146414

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	1.96	ALOGPS
logP	1.45	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.82 m³·mol⁻¹	ChemAxon
Polarizability	29.18 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

Aly AH, Debbab A, Clements C, Edrada-Ebel R, Orlikova B, Diederich M, Wray V, Lin W, Proksch P: NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorg Med Chem. 2011 Jan 1;19(1):414-21. doi: 10.1016/j.bmc.2010.11.012. Epub 2010 Nov 17. [PubMed:21146414 ]

Showing NP-Card for Penilactone (NP0043943)

MOL for NP0043943 (Penilactone)

3D MOL for NP0043943 (Penilactone)

3D SDF for NP0043943 (Penilactone)

3D-SDF for NP0043943 (Penilactone)

PDB for NP0043943 (Penilactone)

3D PDB for NP0043943 (Penilactone)

SMILES for NP0043943 (Penilactone)

INCHI for NP0043943 (Penilactone)

Structure for NP0043943 (Penilactone)

3D Structure for NP0043943 (Penilactone)