NP-MRD: Showing NP-Card for 8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+ (NP0027304)

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Record Information

Version

2.0

Created at

2021-06-19 18:58:01 UTC

Updated at

2021-06-29 23:53:20 UTC

NP-MRD ID

NP0027304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+

Provided By

JEOL Database JEOL Logo

Description

8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+ is found in Montanoa hibiscifolia. 8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+ was first documented in 2004 (Muller, S., et al.). Based on a literature review very few articles have been published on (2R,3R)-2,3-Dimethyloxirane-2-carboxylic acid [(3aS)-4abeta-hydroxy-2-oxo-6beta-methoxy-9-methylene-3alpha,5beta-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4beta-yl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120583D          

 58 61  0  0  0  0            999 V2000
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   -1.3713   -4.6085    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4105   -4.6318   -2.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
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  8 10  1  0  0  0  0
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  3  2  1  0  0  0  0
  2 12  1  0  0  0  0
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 22 23  2  0  0  0  0
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M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192120583D          

 58 61  0  0  0  0            999 V2000
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    2.7697    0.8288    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
  4  5  1  0  0  0  0
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  4  3  1  0  0  0  0
 17 18  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  2  0  0  0  0
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 12 44  1  6  0  0  0
 20 10  1  0  0  0  0
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 19 13  1  0  0  0  0
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  8 10  1  0  0  0  0
 21 22  1  0  0  0  0
 27 24  1  0  0  0  0
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 24 26  1  0  0  0  0
  3  2  1  0  0  0  0
  2 12  1  0  0  0  0
 10 12  1  0  0  0  0
 24 25  1  0  0  0  0
 13 14  1  0  0  0  0
 27 55  1  6  0  0  0
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  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
 24 22  1  1  0  0  0
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  3 31  1  0  0  0  0
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  1 29  1  0  0  0  0
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  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12[C@]([H])(OC(=O)[C@@]3(O[C@]3([H])C([H])([H])[H])C([H])([H])[H])[C@]3([H])[C@@]([H])(OC(=O)[C@]3([H])C([H])([H])[H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]([H])(OC([H])([H])[H])[C@]2([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O7/c1-9-7-8-13(25-6)11(3)21(24)15(9)16-14(10(2)18(22)26-16)17(21)27-19(23)20(5)12(4)28-20/h10-17,24H,1,7-8H2,2-6H3/t10-,11+,12-,13+,14+,15+,16-,17-,20-,21+/m1/s1

> <INCHI_KEY>
SPEMCSKGICNUDT-NGBGBTQPSA-N

> <FORMULA>
C21H30O7

> <MOLECULAR_WEIGHT>
394.464

> <EXACT_MASS>
394.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.35865041976062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,4R,4aS,5S,6S,9aS,9bR)-4a-hydroxy-6-methoxy-3,5-dimethyl-9-methylidene-2-oxo-dodecahydroazuleno[1,2-b]furan-4-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.506943502666667

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.190611912532788

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5902263494581588

> <JCHEM_POLAR_SURFACE_AREA>
94.59

> <JCHEM_REFRACTIVITY>
97.9947

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,4R,4aS,5S,6S,9aS,9bR)-4a-hydroxy-6-methoxy-3,5-dimethyl-9-methylidene-2-oxo-octahydro-3H-azuleno[1,2-b]furan-4-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
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   -1.2443   -1.7309    2.6821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9158   -1.0025    1.3675 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9728    1.6347    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4370    1.8665    0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534    2.2634    3.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5090    0.8989    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -1.9641    3.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3412    2.0893   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9168    4.4178    1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1705    3.1556    2.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  2  1  2  3
  4  3  1  0
 17 18  1  0
 12 13  1  0
 15 16  2  0
 19 20  1  0
 12 44  1  6
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 21 22  1  0
 27 24  1  0
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  3  2  1  0
  2 12  1  0
 10 12  1  0
 24 25  1  0
 13 14  1  0
 27 55  1  6
 14 15  1  0
 27 28  1  0
 15 17  1  0
 22 23  2  0
 19 17  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
 24 22  1  1
  4 33  1  0
  4 34  1  0
  5 35  1  6
  8 39  1  6
  3 31  1  0
  3 32  1  0
 20 51  1  6
 19 50  1  1
 13 45  1  1
 17 46  1  1
  9 40  1  0
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  1 29  1  0
  1 30  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 11 43  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.775  -5.550   1.026  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.371  -4.609   0.273  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.771  -4.937  -1.144  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.530  -3.833  -2.178  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.230  -3.022  -2.046  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.886  -3.821  -1.637  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.411  -4.632  -2.683  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.363  -1.804  -1.080  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.845  -0.886  -1.350  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.496  -2.180   0.427  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.747  -2.725   0.904  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.648  -3.186   0.730  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.958  -2.992   2.234  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.362  -2.722   2.388  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.551  -1.611   3.155  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.648  -1.144   3.413  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.227  -1.096   3.651  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.191   0.414   3.758  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.244  -1.731   2.682  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.916  -1.002   1.367  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.147  -0.075   1.632  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.027   1.209   1.224  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.973   1.635   0.577  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.120   2.070   1.618  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.437   1.867   0.929  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.253   2.263   3.046  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.872   3.414   2.289  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.485   3.938   2.603  0.00  0.00           C+0
HETATM   29  H   UNK     0      -0.592  -6.550   0.642  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.418  -5.360   2.033  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.246  -5.841  -1.480  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.839  -5.189  -1.155  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.388  -3.149  -2.200  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.534  -4.319  -3.163  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.020  -2.612  -3.044  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.662  -5.340  -3.046  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.256  -5.198  -2.282  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.770  -4.007  -3.506  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.262  -1.246  -1.376  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.779  -1.302  -0.958  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.701   0.102  -0.919  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.982  -0.723  -2.425  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.038  -3.374   0.226  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.547  -2.850   0.190  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.718  -3.845   2.875  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.080  -1.534   4.647  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.188   0.764   4.021  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.877   0.756   4.541  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.509   0.899   2.831  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.308  -1.964   3.206  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.811  -0.510   0.967  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.341   2.089  -0.138  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.220   2.513   1.340  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.770   0.829   1.035  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.598   4.206   2.153  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.917   4.418   1.720  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.420   4.687   3.398  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.171   3.156   2.941  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    1    3   12                                                  
CONECT    3    4    2   31   32                                             
CONECT    4    5    3   33   34                                             
CONECT    5    4    6    8   35                                             
CONECT    6    5    7                                                       
CONECT    7    6   36   37   38                                             
CONECT    8    9   10    5   39                                             
CONECT    9    8   40   41   42                                             
CONECT   10   20   11    8   12                                             
CONECT   11   10   43                                                       
CONECT   12   13   44    2   10                                             
CONECT   13   12   19   14   45                                             
CONECT   14   13   15                                                       
CONECT   15   16   14   17                                                  
CONECT   16   15                                                            
CONECT   17   18   15   19   46                                             
CONECT   18   17   47   48   49                                             
CONECT   19   20   13   17   50                                             
CONECT   20   19   10   21   51                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   27   26   25   22                                             
CONECT   25   24   52   53   54                                             
CONECT   26   27   24                                                       
CONECT   27   24   26   55   28                                             
CONECT   28   27   56   57   58                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
   -0.7752   -5.5503    1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713   -4.6085    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7710   -4.9368   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -3.8334   -2.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304   -3.0220   -2.0461 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8855   -3.8212   -1.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105   -4.6318   -2.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632   -1.8036   -1.0804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8454   -0.8860   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -2.1801    0.4274 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7469   -2.7253    0.9042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482   -3.1859    0.7298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9584   -2.9924    2.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3618   -2.7223    2.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511   -1.6107    3.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6477   -1.1437    3.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273   -1.0964    3.6505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1906    0.4141    3.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2443   -1.7309    2.6821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9158   -1.0025    1.3675 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1466   -0.0748    1.6322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268    1.2091    1.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    1.6347    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201    2.0701    1.6183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4370    1.8665    0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2534    2.2634    3.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    3.4142    2.2887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4847    3.9377    2.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -6.5503    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4183   -5.3601    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463   -5.8407   -1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392   -5.1892   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3876   -3.1491   -2.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339   -4.3191   -3.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204   -2.6118   -3.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -5.3405   -3.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559   -5.1977   -2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703   -4.0071   -3.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -1.2465   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -1.3021   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    0.1022   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9823   -0.7232   -2.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377   -3.3739    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -2.8504    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177   -3.8445    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0798   -1.5337    4.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    0.7639    4.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769    0.7562    4.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090    0.8989    2.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -1.9641    3.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8114   -0.5100    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    2.0893   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2202    2.5126    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7697    0.8288    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    4.2057    2.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    4.4178    1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    4.6874    3.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705    3.1556    2.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  2  1  2  3
  4  3  1  0
 17 18  1  0
 12 13  1  0
 15 16  2  0
 19 20  1  0
 12 44  1  6
 20 10  1  0
 10 11  1  1
 19 13  1  0
 20 21  1  0
  8 10  1  0
 21 22  1  0
 27 24  1  0
 26 27  1  0
 24 26  1  0
  3  2  1  0
  2 12  1  0
 10 12  1  0
 24 25  1  0
 13 14  1  0
 27 55  1  6
 14 15  1  0
 27 28  1  0
 15 17  1  0
 22 23  2  0
 19 17  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
 24 22  1  1
  4 33  1  0
  4 34  1  0
  5 35  1  6
  8 39  1  6
  3 31  1  0
  3 32  1  0
 20 51  1  6
 19 50  1  1
 13 45  1  1
 17 46  1  1
  9 40  1  0
  9 41  1  0
  9 42  1  0
  1 29  1  0
  1 30  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 11 43  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(2R,3R)-2,3-Dimethyloxirane-2-carboxylate [(3as)-4abeta-hydroxy-2-oxo-6b-methoxy-9-methylene-3a,5b-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4b-yl ester	Generator
(2R,3R)-2,3-Dimethyloxirane-2-carboxylate [(3as)-4abeta-hydroxy-2-oxo-6beta-methoxy-9-methylene-3alpha,5beta-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4beta-yl ester	Generator
(2R,3R)-2,3-Dimethyloxirane-2-carboxylate [(3as)-4abeta-hydroxy-2-oxo-6β-methoxy-9-methylene-3α,5β-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4β-yl ester	Generator
(2R,3R)-2,3-Dimethyloxirane-2-carboxylic acid [(3as)-4abeta-hydroxy-2-oxo-6b-methoxy-9-methylene-3a,5b-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4b-yl ester	Generator
(2R,3R)-2,3-Dimethyloxirane-2-carboxylic acid [(3as)-4abeta-hydroxy-2-oxo-6β-methoxy-9-methylene-3α,5β-dimethyl-2,3,3abeta,4,4a,5,6,7,8,9,9aalpha,9bbeta-dodecahydroazuleno[1,2-b]furan]-4β-yl ester	Generator

Chemical Formula

C₂₁H₃₀O₇

Average Mass

394.4640 Da

Monoisotopic Mass

394.19915 Da

IUPAC Name

(3R,3aS,4R,4aS,5S,6S,9aS,9bR)-4a-hydroxy-6-methoxy-3,5-dimethyl-9-methylidene-2-oxo-dodecahydroazuleno[1,2-b]furan-4-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Traditional Name

(3R,3aS,4R,4aS,5S,6S,9aS,9bR)-4a-hydroxy-6-methoxy-3,5-dimethyl-9-methylidene-2-oxo-octahydro-3H-azuleno[1,2-b]furan-4-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12[C@]([H])(OC(=O)[C@@]3(O[C@]3([H])C([H])([H])[H])C([H])([H])[H])[C@]3([H])[C@@]([H])(OC(=O)[C@]3([H])C([H])([H])[H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@]([H])(OC([H])([H])[H])[C@]2([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H30O7/c1-9-7-8-13(25-6)11(3)21(24)15(9)16-14(10(2)18(22)26-16)17(21)27-19(23)20(5)12(4)28-20/h10-17,24H,1,7-8H2,2-6H3/t10-,11+,12-,13+,14+,15+,16-,17-,20-,21+/m1/s1

InChI Key

SPEMCSKGICNUDT-NGBGBTQPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Montanoa hibiscifolia	JEOL database	Muller, S., et al, J. Nat. Prod. 67, 622 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.23	ALOGPS
logP	1.51	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.99 m³·mol⁻¹	ChemAxon
Polarizability	41.36 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

10187698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21577292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Muller, S., et al. (2004). Muller, S., et al, J. Nat. Prod. 67, 622 (2004). J. Nat. Prod..

Showing NP-Card for 8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+ (NP0027304)

MOL for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

3D MOL for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

3D SDF for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

3D-SDF for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

PDB for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

3D PDB for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

SMILES for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

INCHI for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

Structure for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)

3D Structure for NP0027304 (8alpha-(2',3'-epoxy-2'-methylbutyryloxy)-9alpha-hydroxy-1alpha-mrthoxy-1,+)