NP-MRD: Showing NP-Card for secochiliolide acid. (NP0039571)

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Record Information

Version

2.0

Created at

2021-06-20 21:57:56 UTC

Updated at

2021-06-30 00:12:59 UTC

NP-MRD ID

NP0039571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

secochiliolide acid.

Provided By

JEOL Database JEOL Logo

Description

Secochiliolide acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. secochiliolide acid. is found in Chiliotrichium rosmarinifolium, Nardophyllum bryoides and Nardophyllum lanatum. secochiliolide acid. was first documented in 2010 (Sanchez, M., et al.). Based on a literature review very few articles have been published on Secochiliolide acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123573D          

 51 53  0  0  0  0            999 V2000
   -1.9083   -2.4742   -1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.8196   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -2.5909    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330   -0.6812   -1.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071    0.0712   -2.5192 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3019    0.1254   -3.6651 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6394    0.7756   -3.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4875    2.3023   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7242   -1.3116   -2.3513 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.1118   -2.3128   -2.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123573D          

 51 53  0  0  0  0            999 V2000
   -1.9083   -2.4742   -1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.8196   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2865    1.9673   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    1.7754    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    2.0523    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.4639    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    0.0015    4.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 18  1  1  0  0  0
 18 17  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  2  0  0  0  0
 13 12  1  0  0  0  0
 11 12  1  0  0  0  0
 17 11  1  0  0  0  0
 20 21  1  0  0  0  0
 11 10  1  0  0  0  0
  7  8  1  0  0  0  0
 20  9  1  0  0  0  0
 21 22  1  0  0  0  0
  4  5  1  0  0  0  0
 22 23  1  0  0  0  0
  5  6  1  0  0  0  0
 23 25  1  0  0  0  0
  6  7  1  0  0  0  0
 23 24  2  0  0  0  0
  7  9  1  0  0  0  0
  4  2  2  3  0  0  0
 12 16  2  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
  2  3  1  0  0  0  0
 20  4  1  0  0  0  0
 18 19  2  0  0  0  0
 11 42  1  1  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 20 46  1  1  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  6  0  0  0
 16 45  1  0  0  0  0
 14 44  1  0  0  0  0
 13 43  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 25 51  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
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])[C@@]1([H])C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]11C(=O)O[C@]([H])(C2=C([H])OC([H])=C2[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-12(2)15-5-4-13(3)20(16(15)6-7-18(21)22)10-17(25-19(20)23)14-8-9-24-11-14/h8-9,11,13,16-17H,4-7,10H2,1-3H3,(H,21,22)/t13-,16+,17+,20-/m1/s1

> <INCHI_KEY>
HXQMNSQWUMHREA-LKCJXIOFSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.05939442745894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-(propan-2-ylidene)-2-oxaspiro[4.5]decan-6-yl]propanoic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.755320995333334

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.73273992737765

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8886154437901106

> <JCHEM_POLAR_SURFACE_AREA>
76.74

> <JCHEM_REFRACTIVITY>
92.42679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-(propan-2-ylidene)-2-oxaspiro[4.5]decan-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -1.9083   -2.4742   -1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.8196   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -2.5909    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330   -0.6812   -1.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071    0.0712   -2.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.1254   -3.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394    0.7756   -3.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4875    2.3023   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008    0.0954   -1.9628 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7242   -1.3116   -2.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455   -1.5658   -1.3664 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8393   -2.5610   -1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1118   -2.3128   -2.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -3.5407   -2.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -4.5326   -2.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -3.9364   -1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -0.2754   -1.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    0.6944   -1.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488    1.8818   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -0.0362   -0.7916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8605    1.2692   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646    1.0657    1.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8802    0.4339    2.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.0410    2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.4176    3.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -3.5477   -1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9222   -2.3996   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -2.0308   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -2.0867    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -2.7710    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2109   -3.5597    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876    1.0845   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -0.3698   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899   -0.8942   -4.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377    0.6671   -4.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    0.5931   -4.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    2.6564   -4.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    2.6582   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500    2.8023   -3.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -2.1042   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294   -1.3014   -3.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633   -1.9066   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5753   -1.3522   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5841   -3.8618   -3.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9408   -4.6115   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -0.7074   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    1.9673   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    1.7754    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    2.0523    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.4639    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    0.0015    4.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 18  1  1
 18 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 11 12  1  0
 17 11  1  0
 20 21  1  0
 11 10  1  0
  7  8  1  0
 20  9  1  0
 21 22  1  0
  4  5  1  0
 22 23  1  0
  5  6  1  0
 23 25  1  0
  6  7  1  0
 23 24  2  0
  7  9  1  0
  4  2  2  3
 12 16  2  0
  2  1  1  0
  9 10  1  0
  2  3  1  0
 20  4  1  0
 18 19  2  0
 11 42  1  1
 10 40  1  0
 10 41  1  0
 20 46  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  6
 16 45  1  0
 14 44  1  0
 13 43  1  0
 21 47  1  0
 21 48  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 22 49  1  0
 22 50  1  0
 25 51  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  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      -1.908  -2.474  -1.448  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.689  -1.820  -0.836  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.188  -2.591   0.363  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.133  -0.681  -1.327  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.707   0.071  -2.519  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.302   0.125  -3.665  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.639   0.776  -3.254  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.488   2.302  -3.226  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.201   0.095  -1.963  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.724  -1.312  -2.351  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.845  -1.566  -1.366  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.839  -2.561  -1.863  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.112  -2.313  -2.456  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.654  -3.541  -2.752  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.804  -4.533  -2.385  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.712  -3.936  -1.845  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.425  -0.275  -1.170  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.511   0.694  -1.461  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.749   1.882  -1.308  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.158  -0.036  -0.792  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.861   1.269  -0.005  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.065   1.066   1.292  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.880   0.434   2.388  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.000  -0.041   2.303  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.218   0.418   3.562  0.00  0.00           O+0
HETATM   26  H   UNK     0      -1.926  -3.548  -1.227  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.922  -2.400  -2.538  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.821  -2.031  -1.038  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.591  -2.087   0.934  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.013  -2.771   1.061  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.211  -3.560   0.044  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.988   1.085  -2.212  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.634  -0.370  -2.894  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.490  -0.894  -4.026  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.138   0.667  -4.511  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.349   0.593  -4.074  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.092   2.656  -4.186  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.806   2.658  -2.456  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.450   2.802  -3.094  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.970  -2.104  -2.325  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.129  -1.301  -3.373  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.463  -1.907  -0.396  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.575  -1.352  -2.637  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.584  -3.862  -3.199  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.941  -4.612  -1.499  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.622  -0.707  -0.068  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.287   1.967  -0.617  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.796   1.775   0.252  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.250   2.052   1.653  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.833   0.464   1.122  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.847   0.002   4.187  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    5    2   20                                                  
CONECT    5    4    6   32   33                                             
CONECT    6    5    7   34   35                                             
CONECT    7    8    6    9   36                                             
CONECT    8    7   37   38   39                                             
CONECT    9   18   20    7   10                                             
CONECT   10   11    9   40   41                                             
CONECT   11   12   17   10   42                                             
CONECT   12   13   11   16                                                  
CONECT   13   14   12   43                                                  
CONECT   14   15   13   44                                                  
CONECT   15   16   14                                                       
CONECT   16   15   12   45                                                  
CONECT   17   18   11                                                       
CONECT   18    9   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21    9    4   46                                             
CONECT   21   20   22   47   48                                             
CONECT   22   21   23   49   50                                             
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   51                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   25                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
   -1.9083   -2.4742   -1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.8196   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -2.5909    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330   -0.6812   -1.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071    0.0712   -2.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.1254   -3.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394    0.7756   -3.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4875    2.3023   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008    0.0954   -1.9628 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7242   -1.3116   -2.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455   -1.5658   -1.3664 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8393   -2.5610   -1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1118   -2.3128   -2.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -3.5407   -2.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -4.5326   -2.3848 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -3.9364   -1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -0.2754   -1.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    0.6944   -1.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488    1.8818   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -0.0362   -0.7916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8605    1.2692   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0646    1.0657    1.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8802    0.4339    2.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.0410    2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.4176    3.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -3.5477   -1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9222   -2.3996   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213   -2.0308   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -2.0867    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -2.7710    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2109   -3.5597    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876    1.0845   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -0.3698   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899   -0.8942   -4.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377    0.6671   -4.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    0.5931   -4.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    2.6564   -4.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    2.6582   -2.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500    2.8023   -3.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -2.1042   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294   -1.3014   -3.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633   -1.9066   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5753   -1.3522   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5841   -3.8618   -3.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9408   -4.6115   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -0.7074   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    1.9673   -0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963    1.7754    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    2.0523    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326    0.4639    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    0.0015    4.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 18  1  1
 18 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 11 12  1  0
 17 11  1  0
 20 21  1  0
 11 10  1  0
  7  8  1  0
 20  9  1  0
 21 22  1  0
  4  5  1  0
 22 23  1  0
  5  6  1  0
 23 25  1  0
  6  7  1  0
 23 24  2  0
  7  9  1  0
  4  2  2  3
 12 16  2  0
  2  1  1  0
  9 10  1  0
  2  3  1  0
 20  4  1  0
 18 19  2  0
 11 42  1  1
 10 40  1  0
 10 41  1  0
 20 46  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  6
 16 45  1  0
 14 44  1  0
 13 43  1  0
 21 47  1  0
 21 48  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 22 49  1  0
 22 50  1  0
 25 51  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

3-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-(propan-2-ylidene)-2-oxaspiro[4.5]decan-6-yl]propanoic acid

Traditional Name

3-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-(propan-2-ylidene)-2-oxaspiro[4.5]decan-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C([H])([H])[C@@]1([H])C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]11C(=O)O[C@]([H])(C2=C([H])OC([H])=C2[H])C1([H])[H]

InChI Identifier

InChI=1S/C20H26O5/c1-12(2)15-5-4-13(3)20(16(15)6-7-18(21)22)10-17(25-19(20)23)14-8-9-24-11-14/h8-9,11,13,16-17H,4-7,10H2,1-3H3,(H,21,22)/t13-,16+,17+,20-/m1/s1

InChI Key

HXQMNSQWUMHREA-LKCJXIOFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Chiliotrichium rosmarinifolium	-	KNApSAcK
Nardophyllum bryoides	JEOL database	Sanchez, M., et al, Phytochem. 71, 1395 (2010)
Nardophyllum lanatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Aromatic monoterpenoid
P-menthane monoterpenoid
Monoterpenoid
Carbocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Heteroaromatic compound
Furan
Oxolane
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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	3.22	ALOGPS
logP	3.76	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.73	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.43 m³·mol⁻¹	ChemAxon
Polarizability	37.06 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

30820354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46933528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sanchez, M., et al. (2010). Sanchez, M., et al, Phytochem. 71, 1395 (2010). Phytochem..

Showing NP-Card for secochiliolide acid. (NP0039571)

MOL for NP0039571 (secochiliolide acid.)

3D MOL for NP0039571 (secochiliolide acid.)

3D SDF for NP0039571 (secochiliolide acid.)

3D-SDF for NP0039571 (secochiliolide acid.)

PDB for NP0039571 (secochiliolide acid.)

3D PDB for NP0039571 (secochiliolide acid.)

SMILES for NP0039571 (secochiliolide acid.)

INCHI for NP0039571 (secochiliolide acid.)

Structure for NP0039571 (secochiliolide acid.)

3D Structure for NP0039571 (secochiliolide acid.)