NP-MRD: Showing NP-Card for alantolactone; isoalantolactone (NP0183698)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 22:39:12 UTC

Updated at

2022-09-03 22:39:12 UTC

NP-MRD ID

NP0183698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alantolactone; isoalantolactone

Description

NSC333843 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. alantolactone; isoalantolactone is found in Inula helenium. Based on a literature review very few articles have been published on NSC333843.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200392D          

 34 38  0  0  1  0            999 V2000
   -1.7389   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7939    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    0.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0151    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296    0.5222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7296    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1585    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1585   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -1.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0151   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9814   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363   -0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7514    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363    0.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209    0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7354    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4499    0.5222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4499    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1644    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1644   -0.7153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1644   -1.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4499   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7354   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  6  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  2  1  6  0  0  0
  6 17  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 19  1  6  0  0  0
 23 34  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
    4.2284    1.1646   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    0.2233   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4278   -1.1927   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588   -1.7340   -0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975   -1.8101   -0.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6588   -1.0119    0.9694 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2633   -1.3029    1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974   -0.6248    0.5515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3193   -1.5740   -0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -0.2849    1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    0.2590    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    1.1487   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4692    1.0878   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2222    1.3938   -2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    0.6891   -0.0699 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9651    0.6385   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9454    0.3830    0.4782 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1903    1.4604   -0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0858    0.8675   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    0.7687   -1.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283    1.4238   -3.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.1667   -1.8480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969   -1.0009   -0.7966 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7748   -1.8268   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.0529    0.1033 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3003   -1.1691   -1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -1.6397    1.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -0.9891    1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6709    0.4612    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    1.1770    0.8302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6044    2.1430   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340    0.3451    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731    0.8357    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    0.0865    0.2151 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9793    2.1687    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2181    1.0002   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3023   -1.2517    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034   -2.4191    1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088   -1.0839    2.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7909   -2.4278    0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -2.0024   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.1061   -1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3183   -1.1510    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405    0.4890    2.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7670    0.8648    1.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -0.5993    0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314    0.8419   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924    2.2250   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227    1.3614   -2.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0061    1.6957   -2.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551    1.4379    0.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -0.2386   -1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    1.5964   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785    1.1463    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173    1.4031    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241    2.0221   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980   -1.5594   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -2.1843    0.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5732   -2.7234   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073   -2.1801   -1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652   -0.4359   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3926   -1.1368   -0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4238   -2.7232    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6612   -1.6015    2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -1.5564    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9573   -1.2130    2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713    0.9722    1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997    0.6407    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    1.8429    1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    1.7804   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6945    2.2195   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    3.1410    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    1.8941    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -0.3259    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  1  6
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  3
 19 34  1  0
 34 33  1  0
 33 32  2  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
  6  7  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 32 30  1  0
 15  8  1  0
  2 17  1  0
 32 25  1  0
  7  8  1  0
 34 23  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
 30 69  1  1
 29 67  1  0
 29 68  1  0
 28 65  1  0
 28 66  1  0
 27 63  1  0
 27 64  1  0
 26 60  1  0
 26 61  1  0
 26 62  1  0
 24 58  1  0
 24 59  1  0
 23 57  1  6
 18 55  1  0
 18 56  1  0
 34 74  1  1
 33 73  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 16 52  1  0
 16 53  1  0
 17 54  1  1
  6 37  1  1
  7 38  1  0
  7 39  1  0
  1 35  1  0
  1 36  1  0
M  END


  Mrv1652309042200392D          

 34 38  0  0  1  0            999 V2000
   -1.7389   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7939    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    0.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993    0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0151    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296    0.5222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7296    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1585    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1585   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -1.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0151   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6993   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9814   -1.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363   -0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7514    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2363    0.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209    0.5222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7354    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4499    0.5222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4499    1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1644    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1644   -0.7153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1644   -1.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4499   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7354   -0.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -0.3028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  6  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  2  1  6  0  0  0
  6 17  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 19  1  6  0  0  0
 23 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC[C@]2(C)C[C@H]3OC(=O)C(=C)[C@H]3C=C12.C[C@]12CCCC(=C)[C@@H]1C[C@H]1[C@@H](C2)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/2C15H20O2/c2*1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3;11-13H,1-2,4-8H2,3H3/t9-,11+,13+,15+;11-,12+,13-,15-/m01/s1

> <INCHI_KEY>
BSIJWVLHHXRGIG-YULDBFNHSA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
26.107046209754024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one; (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_LOGP>
3.357975322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.864710029813113

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.19739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
helenine; isoalantolactone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.246  -2.506   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.770  -1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.675   0.205   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.215   0.205   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.770   1.451   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.305   0.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.028   1.745   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.362   0.975   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.362   2.515   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.696   1.745   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.029   0.975   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.029  -0.565   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.696  -1.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.696  -2.875   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.362  -0.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.028  -1.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.305  -0.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.299  -2.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.774  -1.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.869   0.205   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.329   0.205   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.774   1.451   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.239   0.975   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.573   1.745   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.906   0.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.906   2.515   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.240   1.745   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.574   0.975   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.574  -0.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.240  -1.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.240  -2.875   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.906  -0.565   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.573  -1.335   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.239  -0.565   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    2    6                                                  
CONECT   18   19                                                            
CONECT   19   18   20   34                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   32                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   19   23                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one; (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

helenine; isoalantolactone

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC[C@]2(C)C[C@H]3OC(=O)C(=C)[C@H]3C=C12.C[C@]12CCCC(=C)[C@@H]1C[C@H]1[C@@H](C2)OC(=O)C1=C

InChI Identifier

InChI=1S/2C15H20O2/c2*1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3;11-13H,1-2,4-8H2,3H3/t9-,11+,13+,15+;11-,12+,13-,15-/m01/s1

InChI Key

BSIJWVLHHXRGIG-YULDBFNHSA-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
Inula helenium	LOTUS Database	35616633

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
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Not Available

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	3.36	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

279324

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

315682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for alantolactone; isoalantolactone (NP0183698)

MOL for NP0183698 (alantolactone; isoalantolactone)

3D MOL for NP0183698 (alantolactone; isoalantolactone)

3D SDF for NP0183698 (alantolactone; isoalantolactone)

3D-SDF for NP0183698 (alantolactone; isoalantolactone)

PDB for NP0183698 (alantolactone; isoalantolactone)

3D PDB for NP0183698 (alantolactone; isoalantolactone)

SMILES for NP0183698 (alantolactone; isoalantolactone)

INCHI for NP0183698 (alantolactone; isoalantolactone)

Structure for NP0183698 (alantolactone; isoalantolactone)

3D Structure for NP0183698 (alantolactone; isoalantolactone)