NP-MRD: Showing NP-Card for 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid (NP0152964)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 09:32:54 UTC

Updated at

2022-09-02 09:32:54 UTC

NP-MRD ID

NP0152964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Description

Isoeichlerialactone belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid is found in Aglaia forbesii. 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid was first documented in 2010 (PMID: 21587839). Based on a literature review very few articles have been published on Isoeichlerialactone (PMID: 21580698).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211322D          

 31 34  0  0  1  0            999 V2000
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4263   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -1.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8084    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7388   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.7841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411   -1.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  6  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
  9 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -5.3704   -0.9443    0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4742   -1.2458   -0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639   -2.1120   -1.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0392   -0.9082   -0.6950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3202   -2.2411   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.9487   -1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410   -0.9923   -0.2779 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0572   -1.7670    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450    0.2625   -0.0096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3111    1.2536    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1618    1.1184    0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048    0.1004    0.1860 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1446    0.3931   -0.4390 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2957    0.2547    0.5098 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4553   -1.0909    1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5438    0.6629   -0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4756    1.1019    0.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5024    1.6134    1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8143    2.3099    2.8932 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2091    1.1992    1.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2647   -0.7197   -1.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618   -1.4922   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -0.4784   -0.9662 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7441    0.4859   -2.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963    0.0391    0.3621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7128   -0.3798    1.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541    1.3202    0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179    2.4879    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    3.5403    0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.3035   -0.6618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718    4.7749    0.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4184   -1.2891    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1950   -0.3640    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9948   -1.8167   -1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646   -1.9362   -2.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9350   -3.1744   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -0.4126   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8044   -2.7671   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4106   -2.8507    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -1.6392   -2.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -2.9076   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8199   -2.5658    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.3561    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -1.2313    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1607    0.7222   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023    2.2493    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717    1.4684    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200    0.8822    2.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    2.1349    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -0.8019    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029    1.3992   -0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -1.8886    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -1.4076    0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439   -1.1374    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638    1.4650   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.2474   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1503    1.9099    0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0278    0.2570    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669   -0.2356   -2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -1.3663   -1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -1.7659   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0157   -2.4145   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305    0.2252   -2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641    1.5454   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950    0.4761   -2.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329    0.3493    2.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012   -1.3635    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795   -0.4343    2.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261    1.1747   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761    1.6824   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    3.0303    1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916    2.3342    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    5.1669    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 25  4  1  0
 23  7  1  0
 20 14  1  0
 23 12  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  1 32  1  0
  1 33  1  0
  4 37  1  6
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  6
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  1
 13 51  1  6
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 26 66  1  0
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 31 73  1  0
M  END


  Mrv1652309022211322D          

 31 34  0  0  1  0            999 V2000
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4263   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -1.4097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8084    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7388   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722   -2.7841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411   -1.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  6  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
  9 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@@]2(C)CCC(=O)O2)[C@@]1(C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-17(2)18-9-15-26(5)21(24(18,3)13-11-22(28)29)8-7-19-20(10-14-25(19,26)4)27(6)16-12-23(30)31-27/h18-21H,1,7-16H2,2-6H3,(H,28,29)/t18-,19+,20-,21+,24-,25+,26+,27+/m0/s1

> <INCHI_KEY>
LEKUPXHLKIIVCR-VBQMQKFESA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.26132925561328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(2R)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
5.585525955333333

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.966703743583581

> <JCHEM_PKA_STRONGEST_BASIC>
-7.051485357115371

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
121.07149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(2R)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      11.919  -0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.002   1.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.845   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.662  -2.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.685   0.204   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.794  -0.226   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.842  -1.766   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.116  -2.631   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.607  -2.287   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.242   2.392   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.846  -2.127   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.120  -1.444   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.018  -2.980   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.637  -3.660   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.535  -5.197   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.357  -2.804   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14                                                       
CONECT   21   13   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   12    7   24                                             
CONECT   24   23                                                            
CONECT   25    9    4   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(2R)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

Traditional Name

3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(2R)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@@]2(C)CCC(=O)O2)[C@@]1(C)CCC(O)=O

InChI Identifier

InChI=1S/C27H42O4/c1-17(2)18-9-15-26(5)21(24(18,3)13-11-22(28)29)8-7-19-20(10-14-25(19,26)4)27(6)16-12-23(30)31-27/h18-21H,1,7-16H2,2-6H3,(H,28,29)/t18-,19+,20-,21+,24-,25+,26+,27+/m0/s1

InChI Key

LEKUPXHLKIIVCR-VBQMQKFESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aglaia forbesii	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Seco-podocarpan diterpenoid
Carbocyclic fatty acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Oxolane
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	5.38	ALOGPS
logP	5.59	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.97	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.07 m³·mol⁻¹	ChemAxon
Polarizability	50.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

28288098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49788336

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fun HK, Joycharat N, Voravuthikunchai SP, Chantrapromma S: Absolute configuration of methyl isoeichlerialactone. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 9;66(Pt 7):o1604-5. doi: 10.1107/S1600536810018295. [PubMed:21587839 ]
Fun HK, Joycharat N, Voravuthikunchai SP, Chantrapromma S: Absolute configuration of isoeichlerialactone. Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 20;66(Pt 4):o879-80. doi: 10.1107/S1600536810009499. [PubMed:21580698 ]
LOTUS database [Link]

Showing NP-Card for 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid (NP0152964)

MOL for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D MOL for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D SDF for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D-SDF for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

PDB for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D PDB for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

SMILES for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

INCHI for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

Structure for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)

3D Structure for NP0152964 (3-[(3s,3ar,5ar,6s,7s,9ar,9br)-6,9a,9b-trimethyl-3-[(2r)-2-methyl-5-oxooxolan-2-yl]-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid)