NP-MRD: Showing NP-Card for 12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate (NP0321572)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 23:50:40 UTC

Updated at

2022-09-11 23:50:41 UTC

NP-MRD ID

NP0321572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate

Description

2,12,13-Tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]Nonadec-9-en-15-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate is found in Briareum excavatum. 2,12,13-Tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]Nonadec-9-en-15-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501372D          

 40 44  0  0  0  0            999 V2000
    2.5330   -3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713   -1.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060   -0.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096   -0.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181   -0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727    0.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    2.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165    1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    1.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443    0.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    1.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063    1.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    1.5939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755    0.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102    1.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    2.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450    2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6720    0.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372   -0.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337   -1.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  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  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 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  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  7 40  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
   -4.1800    2.3074    2.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8404    1.9063    1.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    1.6897    2.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433    1.7304    0.2709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    1.3501   -0.2544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5926    2.5380   -0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588    3.4102   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    4.8970   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848    3.1051    0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7122    1.8619    1.2568 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9408    2.1552    1.9730 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8445    2.4060    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6672    3.3575    0.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833    1.3259   -0.0200 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7112    1.0365   -0.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891    1.6237   -0.9789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    0.9776    0.1746 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6680   -0.4048    0.3343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5738   -1.2725    0.9883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.7858    2.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4482   -2.6928    2.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -1.4155    2.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986   -0.9213   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4970   -1.0503   -0.9133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7263   -1.7592   -2.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -2.0688    0.0543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3942   -1.6077    1.3125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -1.7092    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0257   -1.2114    3.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507   -2.2280    1.0808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502   -3.2653    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -3.4408   -0.6311 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2140   -3.0182   -0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6389   -2.2777   -1.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4437   -2.4125   -2.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160    0.1499   -1.1064 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6644   -0.1507   -1.5382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2096    0.0450   -2.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.3373   -2.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    0.5425   -3.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1287    2.7797    3.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6676    3.0277    1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8648    1.4594    2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    1.2169    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435    3.1264   -1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.0719   -1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826    5.0825    0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475    5.5279    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    5.1328   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4545    4.0173    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463    1.2724    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370    0.2239   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.9626   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6589    0.7464   -0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8887   -0.3572    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0879   -3.1661    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -3.4911    3.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1154   -2.1549    3.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637   -0.2627   -1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3655   -1.0536   -3.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683   -2.6437   -2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878   -1.9396   -2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9797   -2.4843   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2609   -2.0760    3.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8293   -0.4755    3.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319   -0.7236    3.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1949   -3.3252    1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7522   -4.2322    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0898   -4.3855   -1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1514   -3.3363   -3.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586   -1.5073   -3.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5306   -2.5453   -2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461    0.5503   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -0.4500   -4.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3336    0.3820   -2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7860   -1.3566   -2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  2  0
 28 27  1  0
 27 26  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 23  1  0
 23 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 17  1  0
 17 16  1  6
 16 14  1  0
 14 15  1  6
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 36 24  1  0
 24 25  1  6
 24 26  1  0
 34 32  1  0
 24 23  1  0
 14 17  1  0
 10 17  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 26 63  1  6
 31 67  1  0
 31 68  1  0
 32 69  1  6
 35 70  1  0
 35 71  1  0
 35 72  1  0
 23 59  1  6
 18 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 10 51  1  1
  9 50  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  6 45  1  0
  6 46  1  0
  5 44  1  1
  1 41  1  0
  1 42  1  0
  1 43  1  0
 36 73  1  6
 39 74  1  0
 39 75  1  0
 39 76  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
M  END


  Mrv1533004201501372D          

 40 44  0  0  0  0            999 V2000
    2.5330   -3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -1.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713   -1.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060   -0.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096   -0.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4784   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181   -0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727    0.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877    2.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165    1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    1.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478    0.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443    0.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    1.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063    1.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    1.5939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755    0.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102    1.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    2.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450    2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7415    1.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6720    0.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372   -0.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337   -1.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436   -1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  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  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 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  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  7 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2OC2(C)C2C(OC(C)=O)C34OC3(C)C(=O)OC4C=C(C)CC(OC(C)=O)C(OC(C)=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O12/c1-12-9-17(34-13(2)29)22(36-15(4)31)25(6)18(35-14(3)30)11-19-26(7,39-19)21(25)23(37-16(5)32)28-20(10-12)38-24(33)27(28,8)40-28/h10,17-23H,9,11H2,1-8H3

> <INCHI_KEY>
UDFAVOZUFNGPCB-UHFFFAOYSA-N

> <FORMULA>
C28H36O12

> <MOLECULAR_WEIGHT>
564.584

> <EXACT_MASS>
564.220676599

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.48689966194151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
0.6839020626666672

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9880550193928967

> <JCHEM_POLAR_SURFACE_AREA>
156.56

> <JCHEM_REFRACTIVITY>
131.2802

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       4.728  -5.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.387  -3.855   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.752  -3.142   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.493  -3.301   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.558  -1.763   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.258  -0.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.893  -1.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.407  -0.825   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.342   0.714   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.442   1.792   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.757   3.171   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.470   4.536   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.964   3.036   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.149   4.437   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.209   2.408   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.023   1.427   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.323   0.602   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.860   2.045   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.878   3.232   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.360   2.975   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.416   4.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.688   1.315   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.752   2.853   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.546   3.810   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.817   4.392   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.117   3.567   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.417   2.741   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.353   1.202   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.653   0.377   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.018   1.090   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.082   2.629   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.318   0.265   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.988   0.489   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.288  -0.336   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.923  -1.049   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.223  -1.875   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.158  -3.413   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.458  -4.239   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.793  -4.127   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.828  -3.189   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   40                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   13   17                                             
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   33                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   23   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   22   34   35                                             
CONECT   34   33                                                            
CONECT   35   33    5   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40    7                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
2,12,13-Tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0,.0,.0,]nonadec-9-en-15-yl acetic acid	Generator
2,12,13-Tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-15-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₆O₁₂

Average Mass

564.5840 Da

Monoisotopic Mass

564.22068 Da

IUPAC Name

12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate

Traditional Name

12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2OC2(C)C2C(OC(C)=O)C34OC3(C)C(=O)OC4C=C(C)CC(OC(C)=O)C(OC(C)=O)C12C

InChI Identifier

InChI=1S/C28H36O12/c1-12-9-17(34-13(2)29)22(36-15(4)31)25(6)18(35-14(3)30)11-19-26(7,39-19)21(25)23(37-16(5)32)28-20(10-12)38-24(33)27(28,8)40-28/h10,17-23H,9,11H2,1-8H3

InChI Key

UDFAVOZUFNGPCB-UHFFFAOYSA-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
Briareum excavatum	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
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Oxepane
Para-dioxane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.27	ALOGPS
logP	0.68	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	156.56 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.28 m³·mol⁻¹	ChemAxon
Polarizability	55.49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73698959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate (NP0321572)

MOL for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

3D MOL for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

3D SDF for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

3D-SDF for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

PDB for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

3D PDB for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

SMILES for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

INCHI for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

Structure for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)

3D Structure for NP0321572 (12,13,15-tris(acetyloxy)-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0³,⁵.0³,⁸.0¹⁷,¹⁹]nonadec-9-en-2-yl acetate)