NP-MRD: Showing NP-Card for (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide (NP0033109)

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Record Information

Version

2.0

Created at

2021-06-19 23:44:51 UTC

Updated at

2021-06-30 00:02:42 UTC

NP-MRD ID

NP0033109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide

Provided By

JEOL Database JEOL Logo

Description

(1R,4S,5S,6S,7S,10R)-1,4-Dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide is found in Mikania campanulata. (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide was first documented in 2007 (PMID: 17616227). Based on a literature review very few articles have been published on (1R,4S,5S,6S,7S,10R)-1,4-Dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101443D          

 47 49  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101443D          

 47 49  0  0  0  0            999 V2000
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  8  9  1  0  0  0  0
 16 18  1  0  0  0  0
  7  6  1  0  0  0  0
 18 19  1  0  0  0  0
 16 23  1  0  0  0  0
 19 20  1  0  0  0  0
 10 12  1  0  0  0  0
 20 21  1  0  0  0  0
 10 23  1  0  0  0  0
 20 22  2  0  0  0  0
 16 17  1  1  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 12 35  1  6  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  7 27  1  1  0  0  0
  6 26  1  6  0  0  0
 13 36  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 21 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 17 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033109

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O6/c1-9-11-4-6-16(3)12(19)5-7-17(21,8-22-10(2)18)14(16)13(11)23-15(9)20/h11-14,19,21H,1,4-8H2,2-3H3/t11-,12-,13-,14+,16-,17+/m0/s1

> <INCHI_KEY>
ARSVQELFNGVTKE-PQTQVYOHSA-N

> <FORMULA>
C17H24O6

> <MOLECULAR_WEIGHT>
324.373

> <EXACT_MASS>
324.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.89467818336212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3aS,5aR,6S,9S,9aS,9bS)-6,9-dihydroxy-5a-methyl-3-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-9-yl]methyl acetate

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
0.5953750116666664

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.739903220777276

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.62261489386161

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9349602929695946

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
80.2139

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3aS,5aR,6S,9S,9aS,9bS)-6,9-dihydroxy-5a-methyl-3-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-9-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -3.5322   -2.1411   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -1.4519   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484   -1.5087    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -1.9361    1.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -0.9428    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -0.8803    0.3445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5880   -0.5361   -0.8216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8545   -0.5965   -2.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    0.3934   -2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864    0.1666   -0.8906 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0422   -1.1619   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    1.3139   -0.8226 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6535    2.5731   -0.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273    1.2162    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239    1.1659    1.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    0.0803    1.7439 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9630   -1.2013    1.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.2318    3.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078    0.6800    4.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882   -0.2411    4.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    0.3429    6.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1926   -1.3757    4.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.1703    0.4541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3038   -2.7810   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -2.0802   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -1.8813    0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821    0.4847   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023   -1.6118   -2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -0.3211   -2.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.3342   -3.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.4068   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810   -2.0317   -1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -1.3729   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5312   -1.1220   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490    1.3127   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    3.2695   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    2.0930    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    0.3422    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    0.9999    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9682    2.1499    1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -1.4452    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087    0.9945    2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -0.7072    3.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    1.1430    5.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533   -0.4360    6.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.7213    6.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    1.1487    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  7  2  1  0
 14 12  1  0
 12 13  1  0
 15 16  1  0
 23 47  1  1
 10  9  1  0
 10 11  1  6
 23  6  1  0
  2  1  2  3
  7  8  1  0
  3  4  2  0
  8  9  1  0
 16 18  1  0
  7  6  1  0
 18 19  1  0
 16 23  1  0
 19 20  1  0
 10 12  1  0
 20 21  1  0
 10 23  1  0
 20 22  2  0
 16 17  1  1
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 12 35  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  7 27  1  1
  6 26  1  6
 13 36  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  1 24  1  0
  1 25  1  0
 18 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.532  -2.141  -1.291  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.707  -1.452  -0.497  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.748  -1.509   0.992  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.653  -1.936   1.682  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.584  -0.943   1.447  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.675  -0.880   0.345  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.588  -0.536  -0.822  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.855  -0.597  -2.148  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.321   0.393  -2.103  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.286   0.167  -0.891  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.042  -1.162  -1.169  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.330   1.314  -0.823  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.654   2.573  -0.780  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.227   1.216   0.413  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.424   1.166   1.714  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.323   0.080   1.744  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.963  -1.201   1.745  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.463   0.232   3.039  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.208   0.680   4.196  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.988  -0.241   4.817  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.601   0.343   6.051  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.193  -1.376   4.408  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.446   0.170   0.454  0.00  0.00           C+0
HETATM   24  H   UNK     0      -4.304  -2.781  -0.870  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.466  -2.080  -2.372  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.233  -1.881   0.249  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.982   0.485  -0.696  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.502  -1.612  -2.361  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.529  -0.321  -2.967  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.877   0.334  -3.047  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.098   1.407  -2.062  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.381  -2.032  -1.181  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.833  -1.373  -0.447  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.531  -1.122  -2.150  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.949   1.313  -1.728  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.331   3.269  -0.835  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.886   2.093   0.456  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.884   0.342   0.348  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.143   1.000   2.525  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.968   2.150   1.884  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.184  -1.445   2.670  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.309   0.995   2.886  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.036  -0.707   3.304  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.293   1.143   5.778  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.153  -0.436   6.585  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.816   0.721   6.712  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.056   1.149   0.522  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2    3    7    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    5   23    7   26                                             
CONECT    7    2    8    6   27                                             
CONECT    8    7    9   28   29                                             
CONECT    9   10    8   30   31                                             
CONECT   10    9   11   12   23                                             
CONECT   11   10   32   33   34                                             
CONECT   12   14   13   10   35                                             
CONECT   13   12   36                                                       
CONECT   14   15   12   37   38                                             
CONECT   15   14   16   39   40                                             
CONECT   16   15   18   23   17                                             
CONECT   17   16   41                                                       
CONECT   18   16   19   42   43                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   44   45   46                                             
CONECT   22   20                                                            
CONECT   23   47    6   16   10                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   21                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
MASTER        0    0    0    0    0    0    0    0   47    0   98    0
END

RDKit          3D

47 49  0  0  0  0  0  0  0  0999 V2000
   -3.5322   -2.1411   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074   -1.4519   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484   -1.5087    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -1.9361    1.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -0.9428    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750   -0.8803    0.3445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5880   -0.5361   -0.8216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8545   -0.5965   -2.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    0.3934   -2.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864    0.1666   -0.8906 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0422   -1.1619   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304    1.3139   -0.8226 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6535    2.5731   -0.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273    1.2162    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239    1.1659    1.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    0.0803    1.7439 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9630   -1.2013    1.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.2318    3.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078    0.6800    4.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882   -0.2411    4.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    0.3429    6.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1926   -1.3757    4.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.1703    0.4541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3038   -2.7810   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -2.0802   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -1.8813    0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821    0.4847   -0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023   -1.6118   -2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -0.3211   -2.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.3342   -3.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.4068   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3810   -2.0317   -1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -1.3729   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5312   -1.1220   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490    1.3127   -1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314    3.2695   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    2.0930    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    0.3422    0.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    0.9999    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9682    2.1499    1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -1.4452    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087    0.9945    2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -0.7072    3.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    1.1430    5.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533   -0.4360    6.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.7213    6.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    1.1487    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  7  2  1  0
 14 12  1  0
 12 13  1  0
 15 16  1  0
 23 47  1  1
 10  9  1  0
 10 11  1  6
 23  6  1  0
  2  1  2  3
  7  8  1  0
  3  4  2  0
  8  9  1  0
 16 18  1  0
  7  6  1  0
 18 19  1  0
 16 23  1  0
 19 20  1  0
 10 12  1  0
 20 21  1  0
 10 23  1  0
 20 22  2  0
 16 17  1  1
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 12 35  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  7 27  1  1
  6 26  1  6
 13 36  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  1 24  1  0
  1 25  1  0
 18 42  1  0
 18 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 17 41  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₆

Average Mass

324.3730 Da

Monoisotopic Mass

324.15729 Da

IUPAC Name

[(3aS,5aR,6S,9S,9aS,9bS)-6,9-dihydroxy-5a-methyl-3-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-9-yl]methyl acetate

Traditional Name

[(3aS,5aR,6S,9S,9aS,9bS)-6,9-dihydroxy-5a-methyl-3-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-9-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H24O6/c1-9-11-4-6-16(3)12(19)5-7-17(21,8-22-10(2)18)14(16)13(11)23-15(9)20/h11-14,19,21H,1,4-8H2,2-3H3/t11-,12-,13-,14+,16-,17+/m0/s1

InChI Key

ARSVQELFNGVTKE-PQTQVYOHSA-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
Mikania campanulata	JEOL database	Krautmann, M., et al, J. Nat. Prod. 70, 1173 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
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	0.79	ALOGPS
logP	0.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.21 m³·mol⁻¹	ChemAxon
Polarizability	33.89 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

16756555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krautmann M, de Riscala EC, Burgueno-Tapia E, Mora-Perez Y, Catalan CA, Joseph-Nathan P: C-15-functionalized eudesmanolides from Mikania campanulata. J Nat Prod. 2007 Jul;70(7):1173-9. doi: 10.1021/np070154t. Epub 2007 Jul 7. [PubMed:17616227 ]
Krautmann, M., et al. (2007). Krautmann, M., et al, J. Nat. Prod. 70, 1173 (2007). J. Nat. Prod..

Showing NP-Card for (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide (NP0033109)

MOL for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

3D MOL for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

3D SDF for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

3D-SDF for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

PDB for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

3D PDB for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

SMILES for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

INCHI for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

Structure for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)

3D Structure for NP0033109 ((1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12-olide)