NP-MRD: Showing NP-Card for penilactone A (NP0041797)

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Record Information

Version

2.0

Created at

2021-06-20 23:37:20 UTC

Updated at

2021-06-30 00:16:31 UTC

NP-MRD ID

NP0041797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

penilactone A

Provided By

JEOL Database JEOL Logo

Description

(3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0³,⁷]Trideca-1(13),9,11-trien-6-one belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3. penilactone A is found in Penicillium crustosum PRB-2 and Penicillium solitum. penilactone A was first documented in 2012 (Wu, G., et al.). Based on a literature review very few articles have been published on (3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0³,⁷]Trideca-1(13),9,11-trien-6-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101373D          

 60 63  0  0  0  0            999 V2000
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   -1.0838   -4.9637   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101373D          

 60 63  0  0  0  0            999 V2000
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    0.5807    2.1172   -3.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978    2.0855   -2.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    1.0487   -2.1023 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1622    0.1542   -2.9088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    1.7228   -1.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1410    2.9066   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441    2.1701   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4006    1.5169    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261   -2.9539   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154   -3.1716   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -6.3305    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -6.5745   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -5.2076    0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -4.1640    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222   -1.1625    3.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047   -2.2244    4.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.8831    3.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.2310    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5063   -1.5432   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -0.6949    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.8004   -2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4390    4.0579   -5.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    4.8790   -5.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    4.6978   -3.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    3.6366   -5.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -0.3527   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    1.0046   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958    3.7417   -1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894    3.2905   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676    2.6208   -2.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -3.9914   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 33  1  0  0  0  0
 14 13  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 28  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 12  1  0  0  0  0
 12 13  1  0  0  0  0
 31 32  2  0  0  0  0
 33  4  2  0  0  0  0
 28 29  1  0  0  0  0
  8 10  2  0  0  0  0
 17 18  1  0  0  0  0
 24 14  2  0  0  0  0
 18 20  2  0  0  0  0
  4  5  1  0  0  0  0
 18 19  1  0  0  0  0
 14 15  1  0  0  0  0
 22 23  1  0  0  0  0
 12 11  1  1  0  0  0
  5  6  2  0  0  0  0
  4  2  1  0  0  0  0
 15 17  2  0  0  0  0
  2  3  2  0  0  0  0
  6  8  1  0  0  0  0
  2  1  1  0  0  0  0
 17 21  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 33 34  1  0  0  0  0
 21 22  2  0  0  0  0
  6  7  1  0  0  0  0
 22 24  1  0  0  0  0
 15 16  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  6  0  0  0
  5 38  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
 13 45  1  0  0  0  0
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 21 51  1  0  0  0  0
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  1 35  1  0  0  0  0
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  1 37  1  0  0  0  0
  9 42  1  0  0  0  0
 34 60  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
 16 47  1  0  0  0  0
 27 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C(C(O[H])=C1C([H])([H])[C@@]12C(=O)O[C@]([H])(C([H])([H])[H])[C@]1(O[H])OC1=C(C(O[H])=C(C([H])=C1C([H])([H])[H])C(=O)C([H])([H])[H])C2([H])[H])C([H])([H])[H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O9/c1-10-6-15(12(3)26)20(29)17(19(10)28)8-24-9-18-21(30)16(13(4)27)7-11(2)22(18)34-25(24,32)14(5)33-23(24)31/h6-7,14,28-30,32H,8-9H2,1-5H3/t14-,24-,25+/m1/s1

> <INCHI_KEY>
PJEDYQWLAZPOEC-ZIHYYHESSA-N

> <FORMULA>
C25H26O9

> <MOLECULAR_WEIGHT>
470.474

> <EXACT_MASS>
470.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.262656412322045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-6-one

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
4.605539651333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.19406711857419

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.003041400030265

> <JCHEM_PKA_STRONGEST_BASIC>
-4.843149079093398

> <JCHEM_POLAR_SURFACE_AREA>
150.58999999999997

> <JCHEM_REFRACTIVITY>
120.90179999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
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   -0.6790   -2.1596    3.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -1.6089    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9900   -1.8444    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -0.9437   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090    0.3489   -1.1753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0802    0.0945   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491    1.2047   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5345    2.4179   -4.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    3.5386   -5.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1867    3.1503   -4.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    4.1476   -4.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    2.1172   -3.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978    2.0855   -2.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    1.0487   -2.1023 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1622    0.1542   -2.9088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    1.7228   -1.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1410    2.9066   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441    2.1701   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139    1.4010   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    1.5169    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261   -2.9539   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154   -3.1716   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -6.3305    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -6.5745   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -5.2076    0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2047   -2.2244    4.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.8831    3.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.2310    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5063   -1.5432   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -0.6949    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.8004   -2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -0.0792   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0545    3.4535   -5.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    3.4694   -6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4390    4.0579   -5.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    4.8790   -5.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    4.6978   -3.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    3.6366   -5.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -0.3527   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    1.0046   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958    3.7417   -1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894    3.2905   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676    2.6208   -2.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -3.9914   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 33  1  0
 14 13  1  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 28 30  1  0
 30 31  1  0
 31 12  1  0
 12 13  1  0
 31 32  2  0
 33  4  2  0
 28 29  1  0
  8 10  2  0
 17 18  1  0
 24 14  2  0
 18 20  2  0
  4  5  1  0
 18 19  1  0
 14 15  1  0
 22 23  1  0
 12 11  1  1
  5  6  2  0
  4  2  1  0
 15 17  2  0
  2  3  2  0
  6  8  1  0
  2  1  1  0
 17 21  1  0
  8  9  1  0
 10 11  1  0
 33 34  1  0
 21 22  2  0
  6  7  1  0
 22 24  1  0
 15 16  1  0
 12 26  1  0
 26 27  1  6
  5 38  1  0
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 21 51  1  0
 28 56  1  1
 29 57  1  0
 29 58  1  0
 29 59  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 42  1  0
 34 60  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
 16 47  1  0
 27 55  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.128  -5.817   0.129  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.084  -4.964  -0.541  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.697  -5.208  -1.685  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.499  -3.798   0.189  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.855  -3.529   1.517  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.303  -2.434   2.197  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.679  -2.160   3.626  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.606  -1.609   1.525  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.140  -0.553   2.209  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.990  -1.844   0.198  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.986  -0.944  -0.516  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.409   0.349  -1.175  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.080   0.095  -1.879  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.349   1.205  -2.791  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.686   1.305  -3.214  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.556   0.350  -2.744  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.104   2.329  -4.081  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.535   2.418  -4.504  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.977   3.539  -5.407  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.330   1.567  -4.104  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.157   3.252  -4.538  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.187   3.150  -4.143  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.194   4.148  -4.651  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.581   2.117  -3.275  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.898   2.086  -2.943  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.408   1.049  -2.102  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.162   0.154  -2.909  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.334   1.723  -1.078  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.141   2.907  -1.594  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.444   2.170  -0.049  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.314   1.401  -0.092  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.401   1.517   0.715  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.426  -2.954  -0.458  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.815  -3.172  -1.759  0.00  0.00           O+0
HETATM   35  H   UNK     0      -1.699  -6.330   0.993  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.480  -6.574  -0.579  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.987  -5.208   0.421  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.558  -4.164   2.047  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.122  -1.163   3.716  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.205  -2.224   4.269  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.414  -2.883   3.995  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.593   0.231   1.976  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.506  -1.543  -1.272  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.775  -0.695   0.207  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.157  -0.800  -2.507  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.704  -0.079  -1.131  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.450   0.537  -3.112  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.054   3.454  -5.582  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.470   3.469  -6.373  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.789   4.505  -4.933  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.439   4.058  -5.209  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.733   4.879  -5.323  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.636   4.698  -3.814  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.984   3.637  -5.210  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.520  -0.353  -3.437  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.038   1.005  -0.639  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.496   3.742  -1.887  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.789   3.291  -0.798  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.768   2.621  -2.444  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.371  -3.991  -2.079  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4   33    5    2                                                  
CONECT    5    4    6   38                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6   39   40   41                                             
CONECT    8   10    6    9                                                  
CONECT    9    8   42                                                       
CONECT   10   33    8   11                                                  
CONECT   11   12   10   43   44                                             
CONECT   12   31   13   11   26                                             
CONECT   13   14   12   45   46                                             
CONECT   14   13   24   15                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   47                                                       
CONECT   17   18   15   21                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   48   49   50                                             
CONECT   20   18                                                            
CONECT   21   17   22   51                                                  
CONECT   22   23   21   24                                                  
CONECT   23   22   52   53   54                                             
CONECT   24   25   14   22                                                  
CONECT   25   24   26                                                       
CONECT   26   25   28   12   27                                             
CONECT   27   26   55                                                       
CONECT   28   26   30   29   56                                             
CONECT   29   28   57   58   59                                             
CONECT   30   28   31                                                       
CONECT   31   30   12   32                                                  
CONECT   32   31                                                            
CONECT   33   10    4   34                                                  
CONECT   34   33   60                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    9                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   34                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
   -2.1282   -5.8167    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0838   -4.9637   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966   -5.2077   -1.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989   -3.7977    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -3.5287    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -2.4343    2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -2.1596    3.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -1.6089    1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -0.5528    2.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900   -1.8444    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -0.9437   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090    0.3489   -1.1753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0802    0.0945   -1.8789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491    1.2047   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6861    1.3049   -3.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556    0.3504   -2.7441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039    2.3292   -4.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5345    2.4179   -4.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    3.5386   -5.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304    1.5670   -4.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565    3.2517   -4.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    3.1503   -4.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    4.1476   -4.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5807    2.1172   -3.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978    2.0855   -2.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    1.0487   -2.1023 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1622    0.1542   -2.9088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345    1.7228   -1.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1410    2.9066   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441    2.1701   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139    1.4010   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    1.5169    0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261   -2.9539   -0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154   -3.1716   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993   -6.3305    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -6.5745   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -5.2076    0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -4.1640    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222   -1.1625    3.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047   -2.2244    4.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4135   -2.8831    3.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.2310    1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5063   -1.5432   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -0.6949    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -0.8004   -2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -0.0792   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4498    0.5370   -3.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0545    3.4535   -5.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    3.4694   -6.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888    4.5054   -4.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390    4.0579   -5.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    4.8790   -5.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    4.6978   -3.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    3.6366   -5.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -0.3527   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0380    1.0046   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958    3.7417   -1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894    3.2905   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676    2.6208   -2.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -3.9914   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 33  1  0
 14 13  1  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 28 30  1  0
 30 31  1  0
 31 12  1  0
 12 13  1  0
 31 32  2  0
 33  4  2  0
 28 29  1  0
  8 10  2  0
 17 18  1  0
 24 14  2  0
 18 20  2  0
  4  5  1  0
 18 19  1  0
 14 15  1  0
 22 23  1  0
 12 11  1  1
  5  6  2  0
  4  2  1  0
 15 17  2  0
  2  3  2  0
  6  8  1  0
  2  1  1  0
 17 21  1  0
  8  9  1  0
 10 11  1  0
 33 34  1  0
 21 22  2  0
  6  7  1  0
 22 24  1  0
 15 16  1  0
 12 26  1  0
 26 27  1  6
  5 38  1  0
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 21 51  1  0
 28 56  1  1
 29 57  1  0
 29 58  1  0
 29 59  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  9 42  1  0
 34 60  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
 16 47  1  0
 27 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₉

Average Mass

470.4740 Da

Monoisotopic Mass

470.15768 Da

IUPAC Name

(3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-6-one

Traditional Name

(3R,4R,7S)-11-acetyl-7-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3,10-dihydroxy-4,13-dimethyl-2,5-dioxatricyclo[7.4.0.0^{3,7}]trideca-1(13),9,11-trien-6-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C([H])=C(C(O[H])=C1C([H])([H])[C@@]12C(=O)O[C@]([H])(C([H])([H])[H])[C@]1(O[H])OC1=C(C(O[H])=C(C([H])=C1C([H])([H])[H])C(=O)C([H])([H])[H])C2([H])[H])C([H])([H])[H])C(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C25H26O9/c1-10-6-15(12(3)26)20(29)17(19(10)28)8-24-9-18-21(30)16(13(4)27)7-11(2)22(18)34-25(24,32)14(5)33-23(24)31/h6-7,14,28-30,32H,8-9H2,1-5H3/t14-,24-,25+/m1/s1

InChI Key

PJEDYQWLAZPOEC-ZIHYYHESSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Penicillium crustosum PRB-2	JEOL database	Wu, G., et al, Tetrahedron 68, 9745 (2012)
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Not Available

Direct Parent

Homoisoflavonoids

Alternative Parents

Substituents

Homoisoflavonoid
Alkyl-phenylketone
Chromane
Benzopyran
1-benzopyran
Acetophenone
Phenylketone
O-cresol
P-cresol
Resorcinol
Benzoyl
Aryl ketone
Aryl alkyl ketone
Phenol
Toluene
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Vinylogous acid
Oxolane
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.44	ALOGPS
logP	4.61	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.9 m³·mol⁻¹	ChemAxon
Polarizability	47.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29215292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71481658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu, G., et al. (2012). Wu, G., et al, Tetrahedron 68, 9745 (2012). Tetrahedron.

Showing NP-Card for penilactone A (NP0041797)

MOL for NP0041797 (penilactone A)

3D MOL for NP0041797 (penilactone A)

3D SDF for NP0041797 (penilactone A)

3D-SDF for NP0041797 (penilactone A)

PDB for NP0041797 (penilactone A)

3D PDB for NP0041797 (penilactone A)

SMILES for NP0041797 (penilactone A)

INCHI for NP0041797 (penilactone A)

Structure for NP0041797 (penilactone A)

3D Structure for NP0041797 (penilactone A)