NP-MRD: Showing NP-Card for 1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+ (NP0026510)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 18:22:00 UTC

Updated at

2021-06-29 23:52:05 UTC

NP-MRD ID

NP0026510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+

Provided By

JEOL Database JEOL Logo

Description

1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+ is found in Mikania thapsoides. 1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+ was first documented in 2003 (Catalan, C. A. N., et al.). Based on a literature review very few articles have been published on [(1R,3R,4R,6S,8E,11S)-9-[(acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradec-8-en-4-yl]methyl 3-methylbut-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120223D          

 58 60  0  0  0  0            999 V2000
    1.4697    1.4987    3.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4125    2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.8794    3.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -1.1287    4.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.7554    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.0900    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6748   -2.0798   -0.2451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1668   -2.2692   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -3.1059    0.9151 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2283   -4.3942    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -5.2448    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -6.5455    1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1227   -4.9996    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671   -1.7414   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9013   -2.3395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6129    0.5498   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0798    1.4231   -3.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.6479   -1.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312    2.9021   -1.1207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8537    2.6088    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    3.6895    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960    4.8272    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    3.2246    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    3.9956    3.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    5.4810    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    3.3771    4.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    1.5031   -1.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4215    0.4227   -1.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    1.4263    0.1888 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5175    0.2460    0.9747 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6021    1.4494    4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.4591    2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -0.9240    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -3.0609   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0085   -1.7921   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6172    1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -3.2236    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -7.2119    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -7.0199    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.3737    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360   -1.9353   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -1.2620   -3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -1.0782   -2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.7117   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935    3.7235   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    3.2074   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1529    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    5.8780    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    5.7294    4.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    6.0068    3.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232    3.5262    5.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973    2.2998    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    3.8382    4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    2.4033   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    0.5550   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.4009    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    2.3718    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486    0.1582    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
 16 18  1  0  0  0  0
  2  1  2  3  0  0  0
 18 19  1  1  0  0  0
 18 17  1  0  0  0  0
 19 20  1  0  0  0  0
 27 29  1  0  0  0  0
 20 21  1  0  0  0  0
 29 30  1  0  0  0  0
 21 23  1  0  0  0  0
  8 14  2  0  0  0  0
 21 22  2  0  0  0  0
  6 30  1  0  0  0  0
 23 24  2  3  0  0  0
  8  7  1  0  0  0  0
 24 25  1  0  0  0  0
  7  6  1  0  0  0  0
 24 26  1  0  0  0  0
  9 10  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
 30  2  1  0  0  0  0
 11 13  2  0  0  0  0
  6  5  1  0  0  0  0
 16 17  1  0  0  0  0
 14 41  1  0  0  0  0
 27 54  1  6  0  0  0
 29 56  1  0  0  0  0
 29 57  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 16 44  1  1  0  0  0
  6 33  1  6  0  0  0
 30 58  1  1  0  0  0
 28 55  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 23 47  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    1.4697    1.4987    3.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4125    2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.8794    3.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -1.1287    4.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.7554    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.0900    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6748   -2.0798   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -2.2692   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -3.1059    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -4.3942    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -5.2448    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -6.5455    1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1227   -4.9996    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671   -1.7414   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9013   -2.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129    0.5498   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0798    1.4231   -3.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.6479   -1.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312    2.9021   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    2.6088    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    3.6895    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960    4.8272    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    3.2246    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    3.9956    3.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    5.4810    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    3.3771    4.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    1.5031   -1.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4215    0.4227   -1.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    1.4263    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    0.2460    0.9747 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6021    1.4494    4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.4591    2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -0.9240    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -3.0609   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0085   -1.7921   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6172    1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -3.2236    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -7.2119    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -7.0199    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.3737    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360   -1.9353   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -1.2620   -3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -1.0782   -2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.7117   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935    3.7235   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    3.2074   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1529    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    5.8780    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    5.7294    4.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    6.0068    3.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232    3.5262    5.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973    2.2998    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    3.8382    4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    2.4033   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    0.5550   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.4009    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    2.3718    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486    0.1582    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
 18 27  1  0
 27 28  1  0
  8  9  1  0
  3  4  2  0
 16 18  1  0
  2  1  2  3
 18 19  1  1
 18 17  1  0
 19 20  1  0
 27 29  1  0
 20 21  1  0
 29 30  1  0
 21 23  1  0
  8 14  2  0
 21 22  2  0
  6 30  1  0
 23 24  2  3
  8  7  1  0
 24 25  1  0
  7  6  1  0
 24 26  1  0
  9 10  1  0
 14 15  1  0
 10 11  1  0
 15 16  1  0
 11 12  1  0
 30  2  1  0
 11 13  2  0
  6  5  1  0
 16 17  1  0
 14 41  1  0
 27 54  1  6
 29 56  1  0
 29 57  1  0
  7 34  1  0
  7 35  1  0
 15 42  1  0
 15 43  1  0
  9 36  1  0
  9 37  1  0
 16 44  1  1
  6 33  1  6
 30 58  1  1
 28 55  1  0
  1 31  1  0
  1 32  1  0
 19 45  1  0
 19 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
M  END


  Mrv1652306192120223D          

 58 60  0  0  0  0            999 V2000
    1.4697    1.4987    3.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4125    2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.8794    3.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -1.1287    4.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.7554    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.0900    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6748   -2.0798   -0.2451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1668   -2.2692   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -3.1059    0.9151 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2283   -4.3942    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -5.2448    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -6.5455    1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1227   -4.9996    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671   -1.7414   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9013   -2.3395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6129    0.5498   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0798    1.4231   -3.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.6479   -1.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312    2.9021   -1.1207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8537    2.6088    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    3.6895    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960    4.8272    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    3.2246    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    3.9956    3.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    5.4810    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    3.3771    4.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    1.5031   -1.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4215    0.4227   -1.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    1.4263    0.1888 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5175    0.2460    0.9747 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6021    1.4494    4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.4591    2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -0.9240    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -3.0609   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0085   -1.7921   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6172    1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -3.2236    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -7.2119    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -7.0199    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.3737    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360   -1.9353   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -1.2620   -3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -1.0782   -2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.7117   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935    3.7235   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    3.2074   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1529    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    5.8780    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    5.7294    4.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    6.0068    3.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232    3.5262    5.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973    2.2998    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    3.8382    4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    2.4033   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    0.5550   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.4009    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    2.3718    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486    0.1582    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
 16 18  1  0  0  0  0
  2  1  2  3  0  0  0
 18 19  1  1  0  0  0
 18 17  1  0  0  0  0
 19 20  1  0  0  0  0
 27 29  1  0  0  0  0
 20 21  1  0  0  0  0
 29 30  1  0  0  0  0
 21 23  1  0  0  0  0
  8 14  2  0  0  0  0
 21 22  2  0  0  0  0
  6 30  1  0  0  0  0
 23 24  2  3  0  0  0
  8  7  1  0  0  0  0
 24 25  1  0  0  0  0
  7  6  1  0  0  0  0
 24 26  1  0  0  0  0
  9 10  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
 30  2  1  0  0  0  0
 11 13  2  0  0  0  0
  6  5  1  0  0  0  0
 16 17  1  0  0  0  0
 14 41  1  0  0  0  0
 27 54  1  6  0  0  0
 29 56  1  0  0  0  0
 29 57  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 16 44  1  1  0  0  0
  6 33  1  6  0  0  0
 30 58  1  1  0  0  0
 28 55  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 23 47  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026510

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-12(2)7-20(25)28-11-22-18(24)9-16-13(3)21(26)29-17(16)8-15(10-27-14(4)23)5-6-19(22)30-22/h5,7,16-19,24H,3,6,8-11H2,1-2,4H3/b15-5+/t16-,17+,18-,19+,22-/m1/s1

> <INCHI_KEY>
IIXZMAXINFNCGN-DGRDYZOHSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.91967297552325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,3R,4R,6S,8E,11S)-9-[(acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-8-en-4-yl]methyl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.858766375333333

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.813803164685751

> <JCHEM_PKA_STRONGEST_BASIC>
-3.317642495766451

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000001

> <JCHEM_REFRACTIVITY>
106.44699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,3R,4R,6S,8E,11S)-9-[(acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-8-en-4-yl]methyl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    1.4697    1.4987    3.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4125    2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.8794    3.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -1.1287    4.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.7554    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.0900    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6748   -2.0798   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -2.2692   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -3.1059    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -4.3942    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -5.2448    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -6.5455    1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1227   -4.9996    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671   -1.7414   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9013   -2.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129    0.5498   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0798    1.4231   -3.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.6479   -1.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312    2.9021   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    2.6088    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    3.6895    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960    4.8272    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    3.2246    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    3.9956    3.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    5.4810    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    3.3771    4.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    1.5031   -1.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4215    0.4227   -1.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    1.4263    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    0.2460    0.9747 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6021    1.4494    4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.4591    2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -0.9240    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -3.0609   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0085   -1.7921   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6172    1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -3.2236    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -7.2119    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -7.0199    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.3737    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360   -1.9353   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -1.2620   -3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -1.0782   -2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.7117   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935    3.7235   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    3.2074   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1529    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    5.8780    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    5.7294    4.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    6.0068    3.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232    3.5262    5.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973    2.2998    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    3.8382    4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    2.4033   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    0.5550   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.4009    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    2.3718    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486    0.1582    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
 18 27  1  0
 27 28  1  0
  8  9  1  0
  3  4  2  0
 16 18  1  0
  2  1  2  3
 18 19  1  1
 18 17  1  0
 19 20  1  0
 27 29  1  0
 20 21  1  0
 29 30  1  0
 21 23  1  0
  8 14  2  0
 21 22  2  0
  6 30  1  0
 23 24  2  3
  8  7  1  0
 24 25  1  0
  7  6  1  0
 24 26  1  0
  9 10  1  0
 14 15  1  0
 10 11  1  0
 15 16  1  0
 11 12  1  0
 30  2  1  0
 11 13  2  0
  6  5  1  0
 16 17  1  0
 14 41  1  0
 27 54  1  6
 29 56  1  0
 29 57  1  0
  7 34  1  0
  7 35  1  0
 15 42  1  0
 15 43  1  0
  9 36  1  0
  9 37  1  0
 16 44  1  1
  6 33  1  6
 30 58  1  1
 28 55  1  0
  1 31  1  0
  1 32  1  0
 19 45  1  0
 19 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.470   1.499   3.226  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.646   0.413   2.461  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.024  -0.879   3.068  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.092  -1.129   4.257  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.257  -1.755   2.064  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.251  -1.090   0.784  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.675  -2.080  -0.245  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.167  -2.269  -0.222  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.389  -3.106   0.915  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.228  -4.394   0.880  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.232  -5.245   1.836  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.507  -6.545   1.762  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.123  -5.000   2.637  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.667  -1.741  -1.143  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.312  -0.901  -2.340  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.613   0.550  -2.156  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.080   1.423  -3.055  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.332   1.648  -1.648  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.331   2.902  -1.121  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.854   2.609   0.181  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.359   3.689   0.828  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.396   4.827   0.397  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.848   3.225   2.147  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.093   3.996   3.224  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.871   5.481   3.313  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.629   3.377   4.490  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.804   1.503  -1.308  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.422   0.423  -1.989  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.120   1.426   0.189  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.518   0.246   0.975  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.602   1.449   4.305  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.183   2.459   2.814  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.307  -0.924   0.532  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.142  -3.061  -0.086  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.009  -1.792  -1.242  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.184  -2.617   1.874  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.475  -3.224   0.815  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.148  -7.212   2.551  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.327  -7.020   0.794  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.576  -6.374   1.914  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.736  -1.935  -1.046  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.928  -1.262  -3.174  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.709  -1.078  -2.677  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.680   0.712  -2.034  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.394   3.724  -1.067  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.159   3.207  -1.773  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.019   2.153   2.203  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.242   5.878   2.514  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.364   5.729   4.252  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.831   6.007   3.293  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.923   3.526   5.314  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.797   2.300   4.388  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.584   3.838   4.761  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.306   2.403  -1.686  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.216   0.555  -2.934  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.212   1.401   0.309  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.795   2.372   0.638  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.449   0.158   0.759  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    3    1   30                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6   30    7    5   33                                             
CONECT    7    8    6   34   35                                             
CONECT    8    9   14    7                                                  
CONECT    9    8   10   36   37                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   38   39   40                                             
CONECT   13   11                                                            
CONECT   14    8   15   41                                                  
CONECT   15   14   16   42   43                                             
CONECT   16   18   15   17   44                                             
CONECT   17   18   16                                                       
CONECT   18   27   16   19   17                                             
CONECT   19   18   20   45   46                                             
CONECT   20   19   21                                                       
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   24   47                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   48   49   50                                             
CONECT   26   24   51   52   53                                             
CONECT   27   18   28   29   54                                             
CONECT   28   27   55                                                       
CONECT   29   27   30   56   57                                             
CONECT   30   29    6    2   58                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
CONECT   58   30                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    1.4697    1.4987    3.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    0.4125    2.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.8794    3.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -1.1287    4.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.7554    2.0639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.0900    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6748   -2.0798   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -2.2692   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -3.1059    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -4.3942    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2317   -5.2448    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5074   -6.5455    1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1227   -4.9996    2.6366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6671   -1.7414   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3116   -0.9013   -2.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129    0.5498   -2.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0798    1.4231   -3.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.6479   -1.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312    2.9021   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8537    2.6088    0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3590    3.6895    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960    4.8272    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479    3.2246    2.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    3.9956    3.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    5.4810    3.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288    3.3771    4.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038    1.5031   -1.3077 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4215    0.4227   -1.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199    1.4263    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    0.2460    0.9747 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6021    1.4494    4.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.4591    2.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067   -0.9240    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -3.0609   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0085   -1.7921   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6172    1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753   -3.2236    0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -7.2119    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -7.0199    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.3737    1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360   -1.9353   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -1.2620   -3.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -1.0782   -2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.7117   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935    3.7235   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1590    3.2074   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1529    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    5.8780    2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    5.7294    4.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306    6.0068    3.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232    3.5262    5.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7973    2.2998    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    3.8382    4.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064    2.4033   -1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    0.5550   -2.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.4009    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951    2.3718    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486    0.1582    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
 18 27  1  0
 27 28  1  0
  8  9  1  0
  3  4  2  0
 16 18  1  0
  2  1  2  3
 18 19  1  1
 18 17  1  0
 19 20  1  0
 27 29  1  0
 20 21  1  0
 29 30  1  0
 21 23  1  0
  8 14  2  0
 21 22  2  0
  6 30  1  0
 23 24  2  3
  8  7  1  0
 24 25  1  0
  7  6  1  0
 24 26  1  0
  9 10  1  0
 14 15  1  0
 10 11  1  0
 15 16  1  0
 11 12  1  0
 30  2  1  0
 11 13  2  0
  6  5  1  0
 16 17  1  0
 14 41  1  0
 27 54  1  6
 29 56  1  0
 29 57  1  0
  7 34  1  0
  7 35  1  0
 15 42  1  0
 15 43  1  0
  9 36  1  0
  9 37  1  0
 16 44  1  1
  6 33  1  6
 30 58  1  1
 28 55  1  0
  1 31  1  0
  1 32  1  0
 19 45  1  0
 19 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1R,3R,4R,6S,8E,11S)-9-[(Acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0,]tetradec-8-en-4-yl]methyl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

[(1R,3R,4R,6S,8E,11S)-9-[(acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-8-en-4-yl]methyl 3-methylbut-2-enoate

Traditional Name

[(1R,3R,4R,6S,8E,11S)-9-[(acetyloxy)methyl]-3-hydroxy-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-8-en-4-yl]methyl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H28O8/c1-12(2)7-20(25)28-11-22-18(24)9-16-13(3)21(26)29-17(16)8-15(10-27-14(4)23)5-6-19(22)30-22/h5,7,16-19,24H,3,6,8-11H2,1-2,4H3/b15-5+/t16-,17+,18-,19+,22-/m1/s1

InChI Key

IIXZMAXINFNCGN-DGRDYZOHSA-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 thapsoides	JEOL database	Catalan, C. A. N., et al, J. Nat. Prod. 66, 949 (2003)

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
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	1.24	ALOGPS
logP	1.86	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.45 m³·mol⁻¹	ChemAxon
Polarizability	42.92 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	Yes	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

9157885

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10982684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Catalan, C. A. N., et al. (2003). Catalan, C. A. N., et al, J. Nat. Prod. 66, 949 (2003). J. Nat. Prod..

Showing NP-Card for 1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+ (NP0026510)

MOL for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

3D MOL for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

3D SDF for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

3D-SDF for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

PDB for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

3D PDB for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

SMILES for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

INCHI for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

Structure for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)

3D Structure for NP0026510 (1(10)E-(3S,4R,5R,7S,8S)-14-acetyloxy-3,4-epoxy-5-hydroxy-15-senecioyloxyg+)