NP-MRD: Showing NP-Card for (1'S)-sporulosol (NP0001543)

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Record Information

Version

1.0

Created at

2020-09-10 21:00:56 UTC

Updated at

2021-08-10 02:55:08 UTC

NP-MRD ID

NP0001543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'S)-sporulosol

Provided By

NPAtlas

Description

(2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxo-6H-benzo[c]chromen-4-yl}oxy)-2,4-dimethyl-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). (1'S)-sporulosol is found in Paraconiothyrium and Paraphaeosphaeria sporulosa. It was first documented in 2018 (PMID: 29799466). Based on a literature review very few articles have been published on (2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxo-6H-benzo[c]chromen-4-yl}oxy)-2,4-dimethyl-2,3-dihydro-1-benzofuran-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 56 60  0  0  0  0            999 V2000
    7.9142   -0.0122    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -0.6515    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5398    3.5162    0.1072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2438    1.4980    0.1004 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


  Mrv1652306242117433D          

 56 60  0  0  0  0            999 V2000
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    4.3242   -0.5919    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334   -0.6980    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    0.3200    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7672    0.8951    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    2.0171    0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    4.2738   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2320    2.8326    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0553   -1.7617    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3049   -1.5557    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8574    0.2390   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8702    2.8826   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8631    1.7518   -2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    2.6242   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -4.1872   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974   -4.0782   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -4.0997    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248   -3.5483    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -2.9041   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142   -3.0416    1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473   -3.8744    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -1.5908    0.7611 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
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 24 25  2  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34  3  1  0  0  0  0
 33  7  1  0  0  0  0
 32 11  1  0  0  0  0
 24 14  1  0  0  0  0
 23 17  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  4 38  1  0  0  0  0
  6 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 28 51  1  0  0  0  0
 29 52  1  0  0  0  0
 31 53  1  0  0  0  0
 31 54  1  0  0  0  0
 31 55  1  0  0  0  0
 34 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)OC3=C(O[C@@]4(OC5=C([H])C([H])=C([H])C(=C5C4=O)C([H])([H])[H])C([H])([H])[H])C(OC([H])([H])[H])=C([H])C(=C3C2=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O8/c1-12-7-6-8-17-20(12)24(28)26(3,33-17)34-22-18(31-5)9-13(2)19-15-10-14(30-4)11-16(27)21(15)25(29)32-23(19)22/h6-11,27H,1-5H3/t26-/m0/s1

> <INCHI_KEY>
PWNYACBJAUETEX-SANMLTNESA-N

> <FORMULA>
C26H22O8

> <MOLECULAR_WEIGHT>
462.454

> <EXACT_MASS>
462.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
48.433935199744255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxo-6H-benzo[c]chromen-4-yl}oxy)-2,4-dimethyl-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
5.606936481

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.404606728900433

> <JCHEM_PKA_STRONGEST_BASIC>
-4.076965071515763

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000002

> <JCHEM_REFRACTIVITY>
122.69749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
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   -6.8677    0.1507   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9021    1.0652   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512    2.1420   -1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    0.9906   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    1.7716   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3209    2.8716   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -1.7155   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7348   -2.3379   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -3.7359   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -2.4673    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -1.9097    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -2.8184    0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.5507    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992    0.1036    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3242   -0.5919    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334   -0.6980    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    0.3200    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7672    0.8951    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    2.0171    0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    4.2738   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7677    1.4918    1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2320    2.8326    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3764    2.3734    1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0553   -1.7617    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3049   -1.5557    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8574    0.2390   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8702    2.8826   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8631    1.7518   -2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    2.6242   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -4.1872   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974   -4.0782   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -4.0997    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248   -3.5483    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -2.9041   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142   -3.0416    1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473   -3.8744    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -1.5908    0.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 14 13  1  6
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 12 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 34  3  1  0
 33  7  1  0
 32 11  1  0
 24 14  1  0
 23 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
 34 56  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       7.914  -0.012   1.218  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.651  -0.652   1.046  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.531   0.110   0.729  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.597   1.443   0.575  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.432   2.171   0.253  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.540   3.516   0.107  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.244   1.498   0.100  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.074   2.153  -0.187  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.085   3.397  -0.336  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.952   1.516  -0.309  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.843   0.222  -0.174  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.390  -0.368  -0.324  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.470   0.433  -0.607  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.313   1.034   0.343  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.590   1.970   1.277  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.008   0.074   1.122  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.336  -0.023   0.727  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.276  -0.966   1.117  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.550  -0.846   0.575  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.868   0.151  -0.301  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.902   1.065  -0.660  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.251   2.142  -1.609  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.621   0.991  -0.150  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.405   1.772  -0.319  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.321   2.872  -0.922  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.515  -1.716  -0.192  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.735  -2.338  -0.335  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.861  -3.736  -0.197  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.593  -2.467   0.088  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.890  -1.910   0.254  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.009  -2.818   0.468  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.981  -0.551   0.121  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.199   0.104   0.263  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.324  -0.592   0.577  0.00  0.00           C+0
HETATM   35  H   UNK     0       8.633  -0.698   1.705  0.00  0.00           H+0
HETATM   36  H   UNK     0       8.316   0.320   0.245  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.767   0.895   1.839  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.516   2.017   0.684  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.009   4.274  -0.093  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.768   1.492   1.833  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.232   2.833   0.711  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.376   2.373   1.978  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.055  -1.762   1.805  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.305  -1.556   0.852  0.00  0.00           H+0
HETATM   45  H   UNK     0      -7.857   0.239  -0.718  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.870   2.883  -1.069  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.863   1.752  -2.457  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.366   2.624  -2.060  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.262  -4.187  -1.031  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.897  -4.078  -0.252  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.363  -4.100   0.743  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.525  -3.548   0.204  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.758  -2.904  -0.358  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.314  -3.042   1.494  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.547  -3.874   0.245  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.381  -1.591   0.761  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   38                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   39                                                       
CONECT    7    5    8   33                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   24                                             
CONECT   15   14   40   41   42                                             
CONECT   16   14   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   44                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   46   47   48                                             
CONECT   23   21   24   17                                                  
CONECT   24   23   25   14                                                  
CONECT   25   24                                                            
CONECT   26   12   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   49   50   51                                             
CONECT   29   26   30   52                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   53   54   55                                             
CONECT   32   30   33   11                                                  
CONECT   33   32   34    7                                                  
CONECT   34   33    3   56                                                  
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    4                                                            
CONECT   39    6                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
CONECT   51   28                                                            
CONECT   52   29                                                            
CONECT   53   31                                                            
CONECT   54   31                                                            
CONECT   55   31                                                            
CONECT   56   34                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

RDKit          3D

56 60  0  0  0  0  0  0  0  0999 V2000
    7.9142   -0.0122    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -0.6515    1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309    0.1100    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971    1.4429    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4319    2.1706    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398    3.5162    0.1072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2438    1.4980    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744    2.1529   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846    3.3974   -0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9518    1.5161   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    0.2220   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3898   -0.3682   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4697    0.4327   -0.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    1.0343    0.3433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5901    1.9704    1.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076    0.0739    1.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3356   -0.0234    0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2762   -0.9659    1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5497   -0.8460    0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8677    0.1507   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9021    1.0652   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512    2.1420   -1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    0.9906   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4047    1.7716   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3209    2.8716   -0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -1.7155   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7348   -2.3379   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607   -3.7359   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -2.4673    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -1.9097    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -2.8184    0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -0.5507    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992    0.1036    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3242   -0.5919    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334   -0.6980    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156    0.3200    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7672    0.8951    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    2.0171    0.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    4.2738   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7677    1.4918    1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2320    2.8326    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3764    2.3734    1.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0553   -1.7617    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3049   -1.5557    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8574    0.2390   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8702    2.8826   -1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8631    1.7518   -2.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658    2.6242   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -4.1872   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974   -4.0782   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -4.0997    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248   -3.5483    0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584   -2.9041   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142   -3.0416    1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473   -3.8744    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -1.5908    0.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 14 13  1  6
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 12 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 34  3  1  0
 33  7  1  0
 32 11  1  0
 24 14  1  0
 23 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 31 53  1  0
 31 54  1  0
 31 55  1  0
 34 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₂₂O₈

Average Mass

462.4540 Da

Monoisotopic Mass

462.13147 Da

IUPAC Name

(2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxo-6H-benzo[c]chromen-4-yl}oxy)-2,4-dimethyl-2,3-dihydro-1-benzofuran-3-one

Traditional Name

(2S)-2-({7-hydroxy-3,9-dimethoxy-1-methyl-6-oxobenzo[c]chromen-4-yl}oxy)-2,4-dimethyl-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)OC3=C(O[C@@]4(OC5=C([H])C([H])=C([H])C(=C5C4=O)C([H])([H])[H])C([H])([H])[H])C(OC([H])([H])[H])=C([H])C(=C3C2=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H22O8/c1-12-7-6-8-17-20(12)24(28)26(3,33-17)34-22-18(31-5)9-13(2)19-15-10-14(30-4)11-16(27)21(15)25(29)32-23(19)22/h6-11,27H,1-5H3/t26-/m0/s1

InChI Key

PWNYACBJAUETEX-SANMLTNESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400Mz, Acetone, simulated)	amy.jystad@pnnl.gov	Not Available	Not Available	2020-09-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Paraconiothyrium	NPAtlas	29799466
Paraphaeosphaeria sporulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Coumarin
2-benzopyran
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Aryl alkyl ketone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.94	ALOGPS
logP	5.61	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.7 m³·mol⁻¹	ChemAxon
Polarizability	48.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA027909

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684132

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao C, Fu P, Zhang Y, Liu X, Ren F, Che Y: Sporulosol, a New Ketal from the Fungus Paraconiothyrium sporulosum. Molecules. 2018 May 25;23(6). pii: molecules23061263. doi: 10.3390/molecules23061263. [PubMed:29799466 ]

Showing NP-Card for (1'S)-sporulosol (NP0001543)

MOL for NP0001543 ((1'S)-sporulosol)

3D MOL for NP0001543 ((1'S)-sporulosol)

3D SDF for NP0001543 ((1'S)-sporulosol)

3D-SDF for NP0001543 ((1'S)-sporulosol)

PDB for NP0001543 ((1'S)-sporulosol)

3D PDB for NP0001543 ((1'S)-sporulosol)

SMILES for NP0001543 ((1'S)-sporulosol)

INCHI for NP0001543 ((1'S)-sporulosol)

Structure for NP0001543 ((1'S)-sporulosol)

3D Structure for NP0001543 ((1'S)-sporulosol)