NP-MRD: Showing NP-Card for (1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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 (NP0280540)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 06:23:15 UTC

Updated at

2022-09-09 06:23:15 UTC

NP-MRD ID

NP0280540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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

Description

Stecholide C belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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 found in Briareum stechei. (1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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 was first documented in 1998 (PMID: 9548870). Based on a literature review very few articles have been published on Stecholide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208232D          

 37 41  0  0  1  0            999 V2000
    5.6781    0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2035   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3937   -1.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8497    0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3384   -0.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7744   -1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6290   -2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3205    1.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    2.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    2.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7480    1.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4805    1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429    2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5181    0.5708    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
  5 36  1  0  0  0  0
 11 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
    2.2054    0.4892    4.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4805    1.0944    2.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740    2.3222    2.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297    0.2842    1.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841    0.7749    0.2408 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0310    0.0234   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896   -1.4384   -0.2513 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2674   -2.1287   -1.3163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4731   -1.9409   -0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3003   -3.2671    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805   -1.0397   -0.2006 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1246   -1.7243   -0.8727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3087   -1.0599   -2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -1.8463    0.0380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7869   -2.0869    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069   -3.1162    0.7297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8275   -4.4389    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855   -3.0779    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5126   -4.0021    1.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982   -1.8728    0.4656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3620   -1.5675   -0.5740 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6574   -0.3349   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    0.9015   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    2.0253   -1.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679    1.0974    0.4946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6184    2.1953    1.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    2.0250    2.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2630    3.1635    2.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6939    0.8818    2.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175    1.3107    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5139    1.3926   -0.4594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0146    1.7522   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040    2.9231   -2.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754    3.2559   -3.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1173    3.7010   -1.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779    0.3253   -0.6111 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0673    0.5091   -2.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172    1.2646    4.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.1144    4.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842   -0.2421    3.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    1.8536    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111    0.2708    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4080    0.4461   -1.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -2.0385    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -3.1725    1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -3.6389    0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9420   -3.9832   -0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143   -1.0068    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -2.7547   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -1.5650   -2.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244   -5.2116    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -4.7491    1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -4.5442   -0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -2.4207   -1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -0.3714   -2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949    2.9536   -1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711    2.0975   -1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5089    1.7529   -2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    0.2279    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056    3.6698    3.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5478    3.8868    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1704    2.8229    3.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324    2.2517    1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963    0.5571    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725    2.3157   -0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5150    3.7871   -4.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158    2.3337   -4.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    3.9469   -3.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6820    1.4581   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131   -0.2535   -2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2327    0.6640   -2.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 31 36  1  0
 36 37  1  6
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 36  5  1  0
  9  7  1  0
 36 11  1  0
 16 14  1  0
 21 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  5 41  1  1
  6 42  1  0
  6 43  1  0
  7 44  1  1
 10 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  1
 12 49  1  6
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 21 54  1  6
 22 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  1
 30 63  1  0
 30 64  1  0
 31 65  1  1
 34 66  1  0
 34 67  1  0
 34 68  1  0
 37 69  1  0
 37 70  1  0
 37 71  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END


  Mrv1652309092208232D          

 37 41  0  0  1  0            999 V2000
    5.6781    0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2035   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3937   -1.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8497    0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3384   -0.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7744   -1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6290   -2.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3205    1.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    2.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    2.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7480    1.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856    0.9503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4805    1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429    2.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5181    0.5708    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
  5 36  1  0  0  0  0
 11 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0280540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2O[C@]2(C)[C@@H]2[C@H](O)[C@]34O[C@@]3(C)C(=O)O[C@H]4\C=C(C)/[C@@H](C[C@H](OC(C)=O)[C@@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O11/c1-11-8-19-26(25(7,37-26)22(31)35-19)21(30)20-23(5,16(33-13(3)28)9-15(11)32-12(2)27)17(34-14(4)29)10-18-24(20,6)36-18/h8,15-21,30H,9-10H2,1-7H3/b11-8-/t15-,16+,17+,18+,19+,20-,21+,23+,24+,25+,26+/m1/s1

> <INCHI_KEY>
FDGGBCRMVGGEKZ-ISUPYZAISA-N

> <FORMULA>
C26H34O11

> <MOLECULAR_WEIGHT>
522.547

> <EXACT_MASS>
522.210111915

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.95365088983763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,5R,8S,9Z,11R,13S,14S,15S,17S,19R)-11,13-bis(acetyloxy)-2-hydroxy-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{3,8}.0^{17,19}]nonadec-9-en-15-yl acetate

> <JCHEM_LOGP>
0.014075186333334488

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.45891360439099

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4728711894393802

> <JCHEM_POLAR_SURFACE_AREA>
150.48999999999998

> <JCHEM_REFRACTIVITY>
122.2391

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5R,8S,9Z,11R,13S,14S,15S,17S,19R)-11,13-bis(acetyloxy)-2-hydroxy-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{3,8}.0^{17,19}]nonadec-9-en-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.599   0.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.302  -0.351   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.372  -1.890   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.935   0.357   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.637  -0.473   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.708  -2.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.410  -2.841   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.113  -3.671   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.043  -2.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.602  -2.675   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.973  -0.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.605   0.114   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.453   1.400   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.308  -0.716   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.498  -1.693   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.057  -2.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.445  -3.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.466  -2.466   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.174  -3.833   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.156  -1.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.059  -0.008   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.129   1.531   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.168   2.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.098   3.899   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.535   1.652   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.465   3.191   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.762   4.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.692   5.559   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.130   3.312   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.832   2.482   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.200   1.774   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.497   2.604   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.427   4.142   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.059   4.851   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.724   4.972   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.270   0.236   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.567   1.066   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   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   36                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14   16                                                       
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31    5   11   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₁

Average Mass

522.5470 Da

Monoisotopic Mass

522.21011 Da

IUPAC Name

(1S,2S,3R,5R,8S,9Z,11R,13S,14S,15S,17S,19R)-11,13-bis(acetyloxy)-2-hydroxy-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{3,8}.0^{17,19}]nonadec-9-en-15-yl acetate

Traditional Name

(1S,2S,3R,5R,8S,9Z,11R,13S,14S,15S,17S,19R)-11,13-bis(acetyloxy)-2-hydroxy-5,10,14,19-tetramethyl-6-oxo-4,7,18-trioxapentacyclo[12.5.0.0^{3,5}.0^{3,8}.0^{17,19}]nonadec-9-en-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2O[C@]2(C)[C@@H]2[C@H](O)[C@]34O[C@@]3(C)C(=O)O[C@H]4\C=C(C)/[C@@H](C[C@H](OC(C)=O)[C@@]12C)OC(C)=O

InChI Identifier

InChI=1S/C26H34O11/c1-11-8-19-26(25(7,37-26)22(31)35-19)21(30)20-23(5,16(33-13(3)28)9-15(11)32-12(2)27)17(34-14(4)29)10-18-24(20,6)36-18/h8,15-21,30H,9-10H2,1-7H3/b11-8-/t15-,16+,17+,18+,19+,20-,21+,23+,24+,25+,26+/m1/s1

InChI Key

FDGGBCRMVGGEKZ-ISUPYZAISA-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 stechei	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
Tetracarboxylic acid or derivatives
Oxepane
Para-dioxane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
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	0.014	ChemAxon
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	150.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.24 m³·mol⁻¹	ChemAxon
Polarizability	51.95 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

10249832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21610126

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodriguez J, Nieto RM, Jimenez C: New Briarane Stecholide Diterpenes from the Indonesian Gorgonian Briareum sp. J Nat Prod. 1998 Mar 27;61(3):313-7. doi: 10.1021/np9703510. [PubMed:9548870 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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 (NP0280540)

MOL for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

3D MOL for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

3D SDF for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

3D-SDF for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

PDB for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

3D PDB for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

SMILES for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

INCHI for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

Structure for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)

3D Structure for NP0280540 ((1s,2s,3r,5r,8s,9z,11r,13s,14s,15s,17s,19r)-11,13-bis(acetyloxy)-2-hydroxy-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)