NP-MRD: Showing NP-Card for pestalotiollide A (NP0040311)

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Record Information

Version

2.0

Created at

2021-06-20 22:30:44 UTC

Updated at

2021-06-30 00:14:09 UTC

NP-MRD ID

NP0040311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pestalotiollide A

Provided By

JEOL Database JEOL Logo

Description

6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]Hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. pestalotiollide A is found in Pestalotiopsis sp. pestalotiollide A was first documented in 2011 (Xu, J., et al.). Based on a literature review very few articles have been published on 6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]Hexadeca-1(12),3(8),4,6,13,15-hexaen-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100303D          

 50 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100303D          

 50 52  0  0  0  0            999 V2000
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   -3.4412   -5.5229    5.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3713   -4.2000    4.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234   -3.9208    6.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -3.6374    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928   -2.8437    4.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
 25 24  1  0  0  0  0
 12 13  2  0  0  0  0
 24 22  2  0  0  0  0
 13  8  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  2  0  0  0  0
 27 28  1  0  0  0  0
 13 14  1  0  0  0  0
 28 11  1  0  0  0  0
  8  6  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
 12 16  1  0  0  0  0
  6  4  1  0  0  0  0
 16 18  1  0  0  0  0
  4  2  1  0  0  0  0
 18 19  1  0  0  0  0
  2  3  1  0  0  0  0
 19 20  1  0  0  0  0
  2  1  2  3  0  0  0
 25 26  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  2  0  0  0  0
 20 27  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  2  0  0  0  0
 22 23  1  0  0  0  0
 27 25  2  0  0  0  0
  4  5  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 24 49  1  0  0  0  0
 21 45  1  0  0  0  0
  6 36  1  6  0  0  0
  7 37  1  0  0  0  0
  4 34  1  6  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 26 50  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
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC3=C([H])C([H])=C(C(OC([H])([H])[H])=C3C(=O)OC([H])([H])C2=C([H])C(=C1[H])C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(O[H])C(=C([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-10(2)17(23)18(24)13-5-6-15-16(20(13)26-4)21(25)27-9-12-7-11(3)8-14(22)19(12)28-15/h5-8,17-18,22-24H,1,9H2,2-4H3/t17-,18+/m1/s1

> <INCHI_KEY>
HHLSDNCZICXJDV-MSOLQXFVSA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.14831252351138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.717115522

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73585691913381

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.395516681354973

> <JCHEM_PKA_STRONGEST_BASIC>
-3.461887312187618

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
102.2573

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -2.7346    0.2760   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655    1.2968   -0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023    2.4066    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270    1.3771   -1.7341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7084    2.6004   -2.4878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    1.3584   -1.0038 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9755    2.6345   -0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    0.2137   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0337    0.4569    1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399   -0.5916    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330   -1.9060    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626   -2.1770    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -1.1207   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -1.3756   -1.8116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -1.5442   -2.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -3.5832    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -4.0213   -0.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508   -4.3646    0.5189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -3.8032    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -3.7353    2.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215   -4.0801    3.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -4.0308    4.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -4.4448    5.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -3.6550    5.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578   -3.3028    4.7212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -2.9435    5.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -3.3086    3.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2459   -2.9365    2.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -0.5323   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6235    0.2165   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001    3.3796   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    2.4102    0.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703    2.3038    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    0.5627   -2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    2.5978   -2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    1.2945   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    3.2781   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    1.4793    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.3758    3.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3620   -0.6536   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818   -2.4019   -3.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7102   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -4.4784    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908   -2.8249    0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -4.4027    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412   -5.5229    5.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3713   -4.2000    4.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234   -3.9208    6.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -3.6374    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928   -2.8437    4.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 25 24  1  0
 12 13  2  0
 24 22  2  0
 13  8  1  0
 22 21  1  0
 21 20  2  0
 27 28  1  0
 13 14  1  0
 28 11  1  0
  8  6  1  0
 11 12  1  0
  6  7  1  0
 12 16  1  0
  6  4  1  0
 16 18  1  0
  4  2  1  0
 18 19  1  0
  2  3  1  0
 19 20  1  0
  2  1  2  3
 25 26  1  0
  9 10  1  0
 16 17  2  0
 20 27  1  0
 14 15  1  0
 10 11  2  0
 22 23  1  0
 27 25  2  0
  4  5  1  0
  9 38  1  0
 10 39  1  0
 19 43  1  0
 19 44  1  0
 24 49  1  0
 21 45  1  0
  6 36  1  6
  7 37  1  0
  4 34  1  6
  3 31  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
 26 50  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
  5 35  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      -2.735   0.276  -0.967  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.865   1.297  -0.856  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.102   2.407   0.132  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.627   1.377  -1.734  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.708   2.600  -2.488  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.752   1.358  -1.004  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.976   2.635  -0.376  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.937   0.214  -0.024  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.034   0.457   1.360  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.140  -0.592   2.276  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.133  -1.906   1.817  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.063  -2.177   0.450  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.992  -1.121  -0.471  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.862  -1.376  -1.812  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.142  -1.544  -2.433  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.037  -3.583   0.008  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.894  -4.021  -0.748  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.051  -4.365   0.519  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.139  -3.803   1.107  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.072  -3.735   2.613  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.221  -4.080   3.352  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.238  -4.031   4.756  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.463  -4.445   5.516  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.078  -3.655   5.438  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.058  -3.303   4.721  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.172  -2.943   5.429  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.062  -3.309   3.322  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.246  -2.937   2.719  0.00  0.00           O+0
HETATM   29  H   UNK     0      -2.580  -0.532  -1.676  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.624   0.217  -0.345  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.100   3.380  -0.369  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.333   2.410   0.909  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.070   2.304   0.635  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.646   0.563  -2.468  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.588   2.598  -2.907  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.543   1.295  -1.761  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.618   3.278  -1.021  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.016   1.479   1.737  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.211  -0.376   3.339  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.362  -0.654  -3.030  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.082  -2.402  -3.110  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.962  -1.710  -1.724  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.949  -4.478   0.807  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.391  -2.825   0.681  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.121  -4.403   2.828  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.441  -5.523   5.703  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.371  -4.200   4.956  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.523  -3.921   6.476  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.051  -3.637   6.524  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.893  -2.844   4.781  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    4    3    1                                                  
CONECT    3    2   31   32   33                                             
CONECT    4    6    2    5   34                                             
CONECT    5    4   35                                                       
CONECT    6    8    7    4   36                                             
CONECT    7    6   37                                                       
CONECT    8    9   13    6                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   39                                                  
CONECT   11   28   12   10                                                  
CONECT   12   13   11   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   40   41   42                                             
CONECT   16   12   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   43   44                                             
CONECT   20   21   19   27                                                  
CONECT   21   22   20   45                                                  
CONECT   22   24   21   23                                                  
CONECT   23   22   46   47   48                                             
CONECT   24   25   22   49                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   50                                                       
CONECT   27   28   20   25                                                  
CONECT   28   27   11                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
   -2.7346    0.2760   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655    1.2968   -0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023    2.4066    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270    1.3771   -1.7341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7084    2.6004   -2.4878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    1.3584   -1.0038 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9755    2.6345   -0.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9367    0.2137   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0337    0.4569    1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399   -0.5916    2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330   -1.9060    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626   -2.1770    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916   -1.1207   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -1.3756   -1.8116 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -1.5442   -2.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -3.5832    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -4.0213   -0.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508   -4.3646    0.5189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -3.8032    1.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -3.7353    2.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215   -4.0801    3.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -4.0308    4.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -4.4448    5.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -3.6550    5.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578   -3.3028    4.7212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720   -2.9435    5.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -3.3086    3.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2459   -2.9365    2.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -0.5323   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6235    0.2165   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001    3.3796   -0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    2.4102    0.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703    2.3038    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    0.5627   -2.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    2.5978   -2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    1.2945   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    3.2781   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    1.4793    1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.3758    3.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3620   -0.6536   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818   -2.4019   -3.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7102   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -4.4784    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908   -2.8249    0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -4.4027    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412   -5.5229    5.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3713   -4.2000    4.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234   -3.9208    6.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -3.6374    6.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928   -2.8437    4.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 25 24  1  0
 12 13  2  0
 24 22  2  0
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 22 21  1  0
 21 20  2  0
 27 28  1  0
 13 14  1  0
 28 11  1  0
  8  6  1  0
 11 12  1  0
  6  7  1  0
 12 16  1  0
  6  4  1  0
 16 18  1  0
  4  2  1  0
 18 19  1  0
  2  3  1  0
 19 20  1  0
  2  1  2  3
 25 26  1  0
  9 10  1  0
 16 17  2  0
 20 27  1  0
 14 15  1  0
 10 11  2  0
 22 23  1  0
 27 25  2  0
  4  5  1  0
  9 38  1  0
 10 39  1  0
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 24 49  1  0
 21 45  1  0
  6 36  1  6
  7 37  1  0
  4 34  1  6
  3 31  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
 26 50  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
  5 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

Traditional Name

6-[(1S,2R)-1,2-dihydroxy-3-methylbut-3-en-1-yl]-16-hydroxy-7-methoxy-14-methyl-2,10-dioxatricyclo[10.4.0.0^{3,8}]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2OC3=C([H])C([H])=C(C(OC([H])([H])[H])=C3C(=O)OC([H])([H])C2=C([H])C(=C1[H])C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(O[H])C(=C([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H22O7/c1-10(2)17(23)18(24)13-5-6-15-16(20(13)26-4)21(25)27-9-12-7-11(3)8-14(22)19(12)28-15/h5-8,17-18,22-24H,1,9H2,2-4H3/t17-,18+/m1/s1

InChI Key

HHLSDNCZICXJDV-MSOLQXFVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Pestalotiopsis sp.	JEOL database	Xu, J., et al, Tetrahedron Lett. 52, 21 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Aromatic alcohol
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	2.24	ALOGPS
logP	2.72	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.26 m³·mol⁻¹	ChemAxon
Polarizability	39.15 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

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

86287669

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu, J., et al. (2011). Xu, J., et al, Tetrahedron Lett. 52, 21 (2011). Tetrahedron Lett.

Showing NP-Card for pestalotiollide A (NP0040311)

MOL for NP0040311 (pestalotiollide A)

3D MOL for NP0040311 (pestalotiollide A)

3D SDF for NP0040311 (pestalotiollide A)

3D-SDF for NP0040311 (pestalotiollide A)

PDB for NP0040311 (pestalotiollide A)

3D PDB for NP0040311 (pestalotiollide A)

SMILES for NP0040311 (pestalotiollide A)

INCHI for NP0040311 (pestalotiollide A)

Structure for NP0040311 (pestalotiollide A)

3D Structure for NP0040311 (pestalotiollide A)