NP-MRD: Showing NP-Card for 9alpha,14-dihydroxy-15-isobutyryloxycostunolide (NP0031370)

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Record Information

Version

2.0

Created at

2021-06-19 22:28:09 UTC

Updated at

2021-06-29 23:59:54 UTC

NP-MRD ID

NP0031370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9alpha,14-dihydroxy-15-isobutyryloxycostunolide

Provided By

JEOL Database JEOL Logo

Description

CHEMBL188503 belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 9alpha,14-dihydroxy-15-isobutyryloxycostunolide is found in Mikania guaco. 9alpha,14-dihydroxy-15-isobutyryloxycostunolide was first documented in 2001 (Rungeler P., et al.). Based on a literature review very few articles have been published on CHEMBL188503.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100283D          

 51 52  0  0  0  0            999 V2000
    1.5342    2.7137   -1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.2273   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    2.4208    0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847    3.0217    1.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    1.8036    1.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4991    1.2242    1.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5153   -0.2366    1.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -0.9973    1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.4634    2.2571 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7074   -3.9556    4.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664   -4.8962    3.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -4.0972    5.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100283D          

 51 52  0  0  0  0            999 V2000
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   -3.5121    1.2723   -3.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    1.5868    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.8063   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324    3.1715   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    2.3396   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809    0.4799   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 16  8  1  0  0  0  0
  8  9  1  0  0  0  0
 19 22  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
 25 24  1  0  0  0  0
 11 13  1  0  0  0  0
 24 22  1  0  0  0  0
 11 12  2  0  0  0  0
 25  6  1  0  0  0  0
 13 14  1  0  0  0  0
  8  7  2  0  0  0  0
  2  1  2  3  0  0  0
 19 18  2  0  0  0  0
  3  4  2  0  0  0  0
 25  2  1  0  0  0  0
 19 20  1  0  0  0  0
 17 16  1  0  0  0  0
 20 21  1  0  0  0  0
 17 18  1  0  0  0  0
 13 15  1  0  0  0  0
  6  5  1  0  0  0  0
 22 23  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 18 43  1  0  0  0  0
  7 29  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 22 47  1  1  0  0  0
 25 51  1  6  0  0  0
  6 28  1  1  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 13 32  1  1  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 23 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])/C([H])([H])C([H])([H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])C([H])([H])[C@@]\1([H])O[H])C([H])([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-11(2)18(22)24-10-13-5-4-6-14(9-20)16(21)8-15-12(3)19(23)25-17(15)7-13/h6-7,11,15-17,20-21H,3-5,8-10H2,1-2H3/b13-7+,14-6-/t15-,16+,17+/m0/s1

> <INCHI_KEY>
RVKFWBVDFTVESX-USHLCOGOSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.25587908196586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3aS,5R,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.7084608020000012

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.283305093141212

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.424726503240521

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7597952307780265

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
93.3642

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3aS,5R,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
    1.5342    2.7137   -1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.2273   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    2.4208    0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847    3.0217    1.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    1.8036    1.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4991    1.2242    1.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5153   -0.2366    1.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -0.9973    1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.4634    2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -2.6610    3.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074   -3.9556    4.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664   -4.8962    3.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -4.0972    5.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5738   -3.6835    5.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -3.3091    6.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -0.4857    2.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -0.9606    0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3669   -0.9968   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422    0.0230   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -0.2585   -2.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757    0.3532   -3.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9013    1.4660   -0.8580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8202    2.1894   -1.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340    2.1618   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428    1.4363   -0.3212 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1366    2.5627   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    3.2763   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661    1.7566    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -0.7100    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416   -2.7696    2.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -3.0736    1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278   -5.1609    5.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9022   -3.8807    6.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -4.2400    4.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201   -2.6167    5.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -3.4949    7.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.2308    6.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392   -3.5975    6.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4312   -0.7935    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    0.6054    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -1.9796    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -0.3557    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655   -1.9992   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    0.1171   -2.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -1.3309   -2.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.2723   -3.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    1.5868    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.8063   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324    3.1715   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    2.3396   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809    0.4799   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
 16  8  1  0
  8  9  1  0
 19 22  1  0
  9 10  1  0
  7  6  1  0
 10 11  1  0
 25 24  1  0
 11 13  1  0
 24 22  1  0
 11 12  2  0
 25  6  1  0
 13 14  1  0
  8  7  2  0
  2  1  2  3
 19 18  2  0
  3  4  2  0
 25  2  1  0
 19 20  1  0
 17 16  1  0
 20 21  1  0
 17 18  1  0
 13 15  1  0
  6  5  1  0
 22 23  1  0
 17 41  1  0
 17 42  1  0
 16 39  1  0
 16 40  1  0
 18 43  1  0
  7 29  1  0
 24 49  1  0
 24 50  1  0
 22 47  1  1
 25 51  1  6
  6 28  1  1
  9 30  1  0
  9 31  1  0
 13 32  1  1
 14 33  1  0
 14 34  1  0
 14 35  1  0
  1 26  1  0
  1 27  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 23 48  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       1.534   2.714  -1.482  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.919   2.227  -0.396  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.466   2.421   0.960  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.485   3.022   1.246  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.643   1.804   1.839  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.499   1.224   1.188  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.515  -0.237   1.566  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.572  -0.997   1.923  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.387  -2.463   2.257  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.776  -2.661   3.619  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.707  -3.956   4.029  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.366  -4.896   3.323  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.119  -4.097   5.480  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.574  -3.684   5.670  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.182  -3.309   6.388  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.994  -0.486   2.007  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.923  -0.961   0.878  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.367  -0.997  -0.524  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.942   0.023  -1.302  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.490  -0.259  -2.721  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.376   0.353  -3.646  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.901   1.466  -0.858  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.820   2.189  -1.683  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.534   2.162  -0.975  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.343   1.436  -0.321  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.137   2.563  -2.480  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.461   3.276  -1.396  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.366   1.757   1.586  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.467  -0.710   1.533  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.342  -2.770   2.133  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.011  -3.074   1.593  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.028  -5.161   5.734  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.902  -3.881   6.696  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.228  -4.240   4.990  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.720  -2.617   5.468  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.416  -3.495   7.442  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.259  -2.231   6.211  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.139  -3.598   6.215  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.431  -0.794   2.967  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.019   0.605   2.055  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.255  -1.980   1.120  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.838  -0.356   0.884  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.365  -1.999  -0.957  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.479   0.117  -2.900  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.474  -1.331  -2.941  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.512   1.272  -3.340  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.266   1.587   0.163  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.702   1.806  -1.510  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.632   3.172  -0.550  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.316   2.340  -2.037  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.181   0.480  -0.835  0.00  0.00           H+0
CONECT    1    2   26   27                                                  
CONECT    2    3    1   25                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    7   25    5   28                                             
CONECT    7    6    8   29                                                  
CONECT    8   16    9    7                                                  
CONECT    9    8   10   30   31                                             
CONECT   10    9   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   32                                             
CONECT   14   13   33   34   35                                             
CONECT   15   13   36   37   38                                             
CONECT   16    8   17   39   40                                             
CONECT   17   16   18   41   42                                             
CONECT   18   19   17   43                                                  
CONECT   19   22   18   20                                                  
CONECT   20   19   21   44   45                                             
CONECT   21   20   46                                                       
CONECT   22   19   24   23   47                                             
CONECT   23   22   48                                                       
CONECT   24   25   22   49   50                                             
CONECT   25   24    6    2   51                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  104    0
END

RDKit          3D

51 52  0  0  0  0  0  0  0  0999 V2000
    1.5342    2.7137   -1.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.2273   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    2.4208    0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847    3.0217    1.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    1.8036    1.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4991    1.2242    1.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5153   -0.2366    1.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -0.9973    1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.4634    2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -2.6610    3.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074   -3.9556    4.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664   -4.8962    3.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -4.0972    5.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5738   -3.6835    5.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -3.3091    6.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -0.4857    2.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229   -0.9606    0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3669   -0.9968   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422    0.0230   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903   -0.2585   -2.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757    0.3532   -3.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9013    1.4660   -0.8580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8202    2.1894   -1.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340    2.1618   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428    1.4363   -0.3212 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1366    2.5627   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    3.2763   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3661    1.7566    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -0.7100    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416   -2.7696    2.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -3.0736    1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278   -5.1609    5.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9022   -3.8807    6.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -4.2400    4.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201   -2.6167    5.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -3.4949    7.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.2308    6.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392   -3.5975    6.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4312   -0.7935    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    0.6054    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -1.9796    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -0.3557    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655   -1.9992   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    0.1171   -2.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -1.3309   -2.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.2723   -3.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    1.5868    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.8063   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324    3.1715   -0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    2.3396   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809    0.4799   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
 16  8  1  0
  8  9  1  0
 19 22  1  0
  9 10  1  0
  7  6  1  0
 10 11  1  0
 25 24  1  0
 11 13  1  0
 24 22  1  0
 11 12  2  0
 25  6  1  0
 13 14  1  0
  8  7  2  0
  2  1  2  3
 19 18  2  0
  3  4  2  0
 25  2  1  0
 19 20  1  0
 17 16  1  0
 20 21  1  0
 17 18  1  0
 13 15  1  0
  6  5  1  0
 22 23  1  0
 17 41  1  0
 17 42  1  0
 16 39  1  0
 16 40  1  0
 18 43  1  0
  7 29  1  0
 24 49  1  0
 24 50  1  0
 22 47  1  1
 25 51  1  6
  6 28  1  1
  9 30  1  0
  9 31  1  0
 13 32  1  1
 14 33  1  0
 14 34  1  0
 14 35  1  0
  1 26  1  0
  1 27  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 23 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

[(3aS,5R,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

Traditional Name

[(3aS,5R,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])/C([H])([H])C([H])([H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])C([H])([H])[C@@]\1([H])O[H])C([H])([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H26O6/c1-11(2)18(22)24-10-13-5-4-6-14(9-20)16(21)8-15-12(3)19(23)25-17(15)7-13/h6-7,11,15-17,20-21H,3-5,8-10H2,1-2H3/b13-7+,14-6-/t15-,16+,17+/m0/s1

InChI Key

RVKFWBVDFTVESX-USHLCOGOSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mikania guaco	JEOL database	Rungeler P., et al, Phytochemistry 56, 475 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.43	ALOGPS
logP	1.71	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	-2.8	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	5	ChemAxon
Refractivity	93.36 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23256993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44398368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rungeler P., et al. (2001). Rungeler P., et al, Phytochemistry 56, 475 (2001) . Phytochem..

Showing NP-Card for 9alpha,14-dihydroxy-15-isobutyryloxycostunolide (NP0031370)

MOL for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

3D MOL for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

3D SDF for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

3D-SDF for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

PDB for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

3D PDB for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

SMILES for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

INCHI for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

Structure for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)

3D Structure for NP0031370 (9alpha,14-dihydroxy-15-isobutyryloxycostunolide)