NP-MRD: Showing NP-Card for teupolin VII (NP0040807)

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Record Information

Version

2.0

Created at

2021-06-20 22:52:28 UTC

Updated at

2021-06-30 00:14:55 UTC

NP-MRD ID

NP0040807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

teupolin VII

Provided By

JEOL Database JEOL Logo

Description

Teupolin VII belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. teupolin VII is found in Teucrium polium L. teupolin VII was first documented in 2011 (Fiorentino, A., et al.). Based on a literature review very few articles have been published on Teupolin VII.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100523D          

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M  END

     RDKit          3D

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  Mrv1652306212100523D          

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   -0.0979   -3.6106    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -6.1448   -2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057   -7.8659   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886   -4.8462    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 15 13  1  0  0  0  0
 24 23  1  0  0  0  0
  3  4  1  0  0  0  0
 23 17  1  0  0  0  0
  4  5  1  0  0  0  0
 18 22  2  0  0  0  0
  7  8  1  0  0  0  0
  6  3  1  0  0  0  0
  3 10  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 16  1  0  0  0  0
 24 25  2  0  0  0  0
 15 16  1  0  0  0  0
 13 14  1  0  0  0  0
  7  6  1  0  0  0  0
  9 38  1  1  0  0  0
 15 24  1  6  0  0  0
  3  2  1  1  0  0  0
  9 15  1  0  0  0  0
  2  1  1  0  0  0  0
 17 48  1  1  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  6  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
 22 51  1  0  0  0  0
 20 50  1  0  0  0  0
 19 49  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(OC([H])([H])[H])C2=C([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]3(C(=O)O[C@]([H])(C4=C([H])OC([H])=C4[H])C3([H])[H])[C@@]2([H])C([H])([H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-13-5-6-15-16(4-3-8-19(15,12-21)23-2)20(13)10-17(25-18(20)22)14-7-9-24-11-14/h6-7,9,11,13,16-17,21H,3-5,8,10,12H2,1-2H3/t13-,16+,17+,19-,20-/m1/s1

> <INCHI_KEY>
WUSIYBBLOFSLDF-VMCMCTHWSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.046218013369554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,5'S,8aS)-5'-(furan-3-yl)-5-(hydroxymethyl)-5-methoxy-2-methyl-3,5,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2'-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.569889059333333

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.314896375524416

> <JCHEM_PKA_STRONGEST_BASIC>
-2.867445817137146

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
92.5248

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,5'S,8aS)-5'-(furan-3-yl)-5-(hydroxymethyl)-5-methoxy-2-methyl-2,3,6,7,8,8a-hexahydrospiro[naphthalene-1,3'-oxolane]-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.6904    0.5362    3.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    0.2116    2.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584    1.1864    1.1511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0273    2.4795    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    2.1855    1.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086    1.5627    1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.3618    1.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915   -0.3948    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452   -0.7915   -0.2336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1473    0.4582   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8325    0.8548   -1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    0.1868   -2.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332   -0.7474   -2.8113 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6586    0.0974   -3.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -1.6314   -1.5398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6707   -2.5382   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549   -3.7687   -0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9792   -4.9832   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7172   -6.0421   -1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622   -6.9277   -1.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6539   -6.4901   -0.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -5.3172   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -3.9104   -1.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371   -2.7158   -1.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674   -2.5760   -2.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.2918    3.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    1.4384    3.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    0.6394    3.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    3.0093    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613    3.1809    0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195    1.2496    1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    2.3040    0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    2.0421    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082   -0.3224    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.7031    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.2868    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413    0.2269   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -1.4306    0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.7226   -1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -0.3714   -2.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    0.9579   -3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470   -1.4012   -3.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317    0.9244   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5715   -0.4963   -3.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.5482   -4.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116   -2.0812   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -2.8151   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -3.6106    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -6.1448   -2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057   -7.8659   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886   -4.8462    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 15 13  1  0
 24 23  1  0
  3  4  1  0
 23 17  1  0
  4  5  1  0
 18 22  2  0
  7  8  1  0
  6  3  1  0
  3 10  1  0
  9  8  1  0
  9 10  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 17 18  1  0
 17 16  1  0
 24 25  2  0
 15 16  1  0
 13 14  1  0
  7  6  1  0
  9 38  1  1
 15 24  1  6
  3  2  1  1
  9 15  1  0
  2  1  1  0
 17 48  1  1
 16 46  1  0
 16 47  1  0
  7 34  1  0
  7 35  1  0
  6 32  1  0
  6 33  1  0
  8 36  1  0
  8 37  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  6
  4 29  1  0
  4 30  1  0
  5 31  1  0
 22 51  1  0
 20 50  1  0
 19 49  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
  1 26  1  0
  1 27  1  0
  1 28  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      -0.690   0.536   3.451  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.708   0.212   2.068  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.158   1.186   1.151  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.027   2.479   1.198  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.425   2.186   1.103  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.309   1.563   1.471  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.255   0.362   1.451  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.192  -0.395   0.123  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.745  -0.792  -0.234  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.147   0.458  -0.208  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.833   0.855  -1.302  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.780   0.187  -2.647  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.433  -0.747  -2.811  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.659   0.097  -3.193  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.577  -1.631  -1.540  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.671  -2.538  -1.421  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.155  -3.769  -0.706  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.979  -4.983  -0.969  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.717  -6.042  -1.887  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.762  -6.928  -1.774  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.654  -6.490  -0.850  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.176  -5.317  -0.364  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.184  -3.910  -1.185  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.637  -2.716  -1.663  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.767  -2.576  -2.101  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.159  -0.292   3.992  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.269   1.438   3.662  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.330   0.639   3.826  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.884   3.009   2.146  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.761   3.181   0.400  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.519   1.250   1.368  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.665   2.304   0.742  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.381   2.042   2.454  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.008  -0.322   2.271  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.282   0.703   1.626  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.820  -1.287   0.219  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.641   0.227  -0.656  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.412  -1.431   0.596  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.488   1.723  -1.264  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.713  -0.371  -2.790  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.766   0.958  -3.427  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.247  -1.401  -3.675  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.832   0.924  -2.500  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.571  -0.496  -3.264  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.502   0.548  -4.181  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.512  -2.081  -0.888  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.037  -2.815  -2.420  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.098  -3.611   0.378  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.135  -6.145  -2.545  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.006  -7.866  -2.252  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.789  -4.846   0.393  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    4    6   10    2                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4   31                                                       
CONECT    6    3    7   32   33                                             
CONECT    7    8    6   34   35                                             
CONECT    8    7    9   36   37                                             
CONECT    9    8   10   38   15                                             
CONECT   10   11    3    9                                                  
CONECT   11   10   12   39                                                  
CONECT   12   11   13   40   41                                             
CONECT   13   12   15   14   42                                             
CONECT   14   13   43   44   45                                             
CONECT   15   13   16   24    9                                             
CONECT   16   17   15   46   47                                             
CONECT   17   23   18   16   48                                             
CONECT   18   22   19   17                                                  
CONECT   19   20   18   49                                                  
CONECT   20   21   19   50                                                  
CONECT   21   22   20                                                       
CONECT   22   18   21   51                                                  
CONECT   23   24   17                                                       
CONECT   24   23   25   15                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

RDKit          3D

51 54  0  0  0  0  0  0  0  0999 V2000
   -0.6904    0.5362    3.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    0.2116    2.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584    1.1864    1.1511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0273    2.4795    1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    2.1855    1.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086    1.5627    1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.3618    1.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1915   -0.3948    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452   -0.7915   -0.2336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1473    0.4582   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8325    0.8548   -1.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    0.1868   -2.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4332   -0.7474   -2.8113 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6586    0.0974   -3.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -1.6314   -1.5398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6707   -2.5382   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549   -3.7687   -0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9792   -4.9832   -0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7172   -6.0421   -1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7622   -6.9277   -1.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6539   -6.4901   -0.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -5.3172   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837   -3.9104   -1.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371   -2.7158   -1.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674   -2.5760   -2.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.2918    3.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    1.4384    3.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303    0.6394    3.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    3.0093    2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7613    3.1809    0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195    1.2496    1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    2.3040    0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    2.0421    2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082   -0.3224    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.7031    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.2868    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413    0.2269   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -1.4306    0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.7226   -1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7133   -0.3714   -2.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    0.9579   -3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470   -1.4012   -3.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8317    0.9244   -2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5715   -0.4963   -3.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016    0.5482   -4.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116   -2.0812   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -2.8151   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -3.6106    0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -6.1448   -2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057   -7.8659   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886   -4.8462    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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  4  5  1  0
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  7  8  1  0
  6  3  1  0
  3 10  1  0
  9  8  1  0
  9 10  1  0
 22 21  1  0
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 17 18  1  0
 17 16  1  0
 24 25  2  0
 15 16  1  0
 13 14  1  0
  7  6  1  0
  9 38  1  1
 15 24  1  6
  3  2  1  1
  9 15  1  0
  2  1  1  0
 17 48  1  1
 16 46  1  0
 16 47  1  0
  7 34  1  0
  7 35  1  0
  6 32  1  0
  6 33  1  0
  8 36  1  0
  8 37  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  6
  4 29  1  0
  4 30  1  0
  5 31  1  0
 22 51  1  0
 20 50  1  0
 19 49  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(1R,2R,5S,5'S,8aS)-5'-(furan-3-yl)-5-(hydroxymethyl)-5-methoxy-2-methyl-3,5,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2'-one

Traditional Name

(1R,2R,5S,5'S,8aS)-5'-(furan-3-yl)-5-(hydroxymethyl)-5-methoxy-2-methyl-2,3,6,7,8,8a-hexahydrospiro[naphthalene-1,3'-oxolane]-2'-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1(OC([H])([H])[H])C2=C([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]3(C(=O)O[C@]([H])(C4=C([H])OC([H])=C4[H])C3([H])[H])[C@@]2([H])C([H])([H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C20H26O5/c1-13-5-6-15-16(4-3-8-19(15,12-21)23-2)20(13)10-17(25-18(20)22)14-7-9-24-11-14/h6-7,9,11,13,16-17,21H,3-5,8,10,12H2,1-2H3/t13-,16+,17+,19-,20-/m1/s1

InChI Key

WUSIYBBLOFSLDF-VMCMCTHWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Teucrium polium	JEOL database	Fiorentino, A., et al, Phytochem. 72, 2037 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Gamma butyrolactone
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary 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	3.05	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.52 m³·mol⁻¹	ChemAxon
Polarizability	37.05 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

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

54598290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fiorentino, A., et al. (2011). Fiorentino, A., et al, Phytochem. 72, 2037 (2011). Phytochem..

Showing NP-Card for teupolin VII (NP0040807)

MOL for NP0040807 (teupolin VII)

3D MOL for NP0040807 (teupolin VII)

3D SDF for NP0040807 (teupolin VII)

3D-SDF for NP0040807 (teupolin VII)

PDB for NP0040807 (teupolin VII)

3D PDB for NP0040807 (teupolin VII)

SMILES for NP0040807 (teupolin VII)

INCHI for NP0040807 (teupolin VII)

Structure for NP0040807 (teupolin VII)

3D Structure for NP0040807 (teupolin VII)