NP-MRD: Showing NP-Card for Sequoiatone E (NP0003921)

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Record Information

Version

2.0

Created at

2020-12-09 01:28:00 UTC

Updated at

2021-07-15 16:47:44 UTC

NP-MRD ID

NP0003921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sequoiatone E

Provided By

NPAtlas

Description

Sequoiatone E is found in Aspergillus parasiticus. Based on a literature review very few articles have been published on methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethyl-6H,7H-cyclopenta[c]pyran-5-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 58 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117513D          

 58 59  0  0  0  0            999 V2000
   -0.1771    2.0821    3.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3927   -3.6905    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1364   -0.6520   -3.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1186    0.4421   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5579   -1.2843   -2.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4211    1.4578    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1131    2.5543    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0924    2.9073   -0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952    1.2140   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    2.4905   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4530   -1.3268    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700   -1.1088   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617    1.8448   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720    0.5480   -1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.3576    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.1142    0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408    0.7678    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097   -0.9235    1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2153   -0.5752   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6656   -0.0084   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -2.1392   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756   -2.3537   -2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013   -4.0867   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.9427    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -2.2672   -0.0639 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16  5  1  0  0  0  0
 12  6  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
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 14 39  1  0  0  0  0
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 20 42  1  1  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
 28 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(C(=O)C(\[H])=C1/C(C(=O)OC([H])([H])[H])=C2C([H])=C([H])OC(=C2[C@@]1(O[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O6/c1-14(9-7-5-6-8-11-23)18(24)13-17-19(21(25)27-4)16-10-12-28-15(2)20(16)22(17,3)26/h10,12-14,23,26H,5-9,11H2,1-4H3/b17-13+/t14-,22+/m0/s1

> <INCHI_KEY>
BJRVUWKADRHSIV-TVXHFNGESA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.476

> <EXACT_MASS>
390.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.10541652278333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethyl-6H,7H-cyclopenta[c]pyran-5-carboxylate

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
1.9216350213333315

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.84394282167507

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.528927678181422

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9919904208717902

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
109.73509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethylcyclopenta[c]pyran-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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    3.2419   -0.0988    0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -0.1850    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236   -0.6852   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6585   -2.0648   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1670   -3.1002   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457   -3.1658   -0.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2542   -0.7795   -0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4700   -1.1088   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617    1.8448   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720    0.5480   -1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.3576    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.1142    0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408    0.7678    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097   -0.9235    1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2153   -0.5752   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7181   -2.9427    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -2.2672   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  3  5  1  0
  5  6  2  0
  6  7  1  0
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  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  6
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16  5  1  0
 12  6  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 20 42  1  1
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
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 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  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      -0.177   2.082   3.455  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.953   1.825   2.290  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.518   0.613   1.972  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.329  -0.349   2.757  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.323   0.425   0.804  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.037  -0.611   0.429  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.285  -1.948   0.977  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.230  -2.696   0.466  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.003  -2.247  -0.583  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.840  -0.990  -1.164  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.708  -0.569  -2.294  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.909  -0.186  -0.694  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.630   1.293  -0.961  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.602   2.115  -0.185  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.646   1.507  -2.310  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.238   1.327  -0.377  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.161   1.792  -0.910  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.191   1.575  -0.588  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.976   2.398  -1.293  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.004   0.728   0.252  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.658  -0.723  -0.122  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.517   0.810  -0.232  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.242  -0.099   0.710  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.708  -0.185   0.468  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.124  -0.685  -0.870  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.659  -2.065  -1.184  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.167  -3.100  -0.210  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.546  -3.166  -0.177  0.00  0.00           O+0
HETATM   29  H   UNK     0       0.028   1.129   3.998  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.753   2.614   3.186  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.799   2.705   4.123  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.647  -2.273   1.821  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.393  -3.691   0.895  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.136  -0.652  -3.257  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.119   0.442  -2.155  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.558  -1.284  -2.371  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.421   1.458   0.170  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.113   2.554   0.714  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.092   2.907  -0.788  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.795   1.214  -2.703  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.371   2.490  -1.782  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.131   0.906   1.295  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.254  -0.780  -0.755  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.453  -1.327   0.771  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.470  -1.109  -0.753  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.862   1.845  -0.091  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.572   0.548  -1.286  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.120   0.358   1.737  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.823  -1.114   0.767  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.241   0.768   0.735  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.110  -0.924   1.225  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.215  -0.575  -1.020  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.666  -0.008  -1.647  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.559  -2.139  -1.247  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.076  -2.354  -2.186  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.801  -4.087  -0.561  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.718  -2.943   0.801  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.898  -2.267  -0.064  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   34   35   36                                             
CONECT   12   10   13    6                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13   37   38   39                                             
CONECT   15   13   40                                                       
CONECT   16   13   17    5                                                  
CONECT   17   16   18   41                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   42                                             
CONECT   21   20   43   44   45                                             
CONECT   22   20   23   46   47                                             
CONECT   23   22   24   48   49                                             
CONECT   24   23   25   50   51                                             
CONECT   25   24   26   52   53                                             
CONECT   26   25   27   54   55                                             
CONECT   27   26   28   56   57                                             
CONECT   28   27   58                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  118    0
END

RDKit          3D

58 59  0  0  0  0  0  0  0  0999 V2000
   -0.1771    2.0821    3.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    1.8252    2.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175    0.6126    1.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293   -0.3489    2.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.4245    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0372   -0.6109    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2850   -1.9480    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -2.6960    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027   -2.2473   -0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8405   -0.9897   -1.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7082   -0.5687   -2.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9094   -0.1862   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6296    1.2926   -0.9613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6024    2.1149   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6456    1.5066   -2.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    1.3274   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1606    1.7920   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907    1.5750   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764    2.3978   -1.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040    0.7275    0.2524 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6583   -0.7231   -0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173    0.8097   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419   -0.0988    0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7082   -0.1850    0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236   -0.6852   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6585   -2.0648   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1670   -3.1002   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457   -3.1658   -0.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282    1.1285    3.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7533    2.6144    3.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990    2.7051    4.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -2.2734    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927   -3.6905    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1364   -0.6520   -3.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1186    0.4421   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5579   -1.2843   -2.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4211    1.4578    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1131    2.5543    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0924    2.9073   -0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952    1.2140   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    2.4905   -1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1314    0.9055    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -0.7795   -0.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -1.3268    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700   -1.1088   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617    1.8448   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720    0.5480   -1.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.3576    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.1142    0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408    0.7678    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097   -0.9235    1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2153   -0.5752   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6656   -0.0084   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585   -2.1392   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756   -2.3537   -2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013   -4.0867   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.9427    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -2.2672   -0.0639 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  6
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16  5  1  0
 12  6  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 20 42  1  1
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethyl-6H,7H-cyclopenta[c]pyran-5-carboxylic acid	Generator

Chemical Formula

C₂₂H₃₀O₆

Average Mass

390.4760 Da

Monoisotopic Mass

390.20424 Da

IUPAC Name

methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethyl-6H,7H-cyclopenta[c]pyran-5-carboxylate

Traditional Name

methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethylcyclopenta[c]pyran-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C=COC(C)=C2[C@](C)(O)\C1=C\C(=O)[C@@H](C)CCCCCCO

InChI Identifier

InChI=1S/C22H30O6/c1-14(9-7-5-6-8-11-23)18(24)13-17-19(21(25)27-4)16-10-12-28-15(2)20(16)22(17,3)26/h10,12-14,23,26H,5-9,11H2,1-4H3/b17-13+/t14-,22+/m0/s1

InChI Key

BJRVUWKADRHSIV-TVXHFNGESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus parasiticus	NPAtlas	11678666
Sequoia sempervirens	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Aspergillus parasiticus RDWD1-2	KNApSAcK Database	22123792

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	2.81	ALOGPS
logP	1.92	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	109.74 m³·mol⁻¹	ChemAxon
Polarizability	43.11 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA011430

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9048121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10872842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Sequoiatone E (NP0003921)

MOL for NP0003921 (Sequoiatone E)

3D MOL for NP0003921 (Sequoiatone E)

3D SDF for NP0003921 (Sequoiatone E)

3D-SDF for NP0003921 (Sequoiatone E)

PDB for NP0003921 (Sequoiatone E)

3D PDB for NP0003921 (Sequoiatone E)

SMILES for NP0003921 (Sequoiatone E)

INCHI for NP0003921 (Sequoiatone E)

Structure for NP0003921 (Sequoiatone E)

3D Structure for NP0003921 (Sequoiatone E)