NP-MRD: Showing NP-Card for (1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate (NP0195926)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 13:53:30 UTC

Updated at

2022-09-04 13:53:30 UTC

NP-MRD ID

NP0195926

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate

Description

Briarein C belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate is found in Briareum asbestinum. (1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate was first documented in 1991 (PMID: 1675176). Based on a literature review very few articles have been published on Briarein C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215532D          

 43 45  0  0  1  0            999 V2000
    0.7818   10.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    9.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738    9.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    8.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    7.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3789    7.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8638    8.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282    9.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    8.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    7.0979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0075    7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    6.6854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6518    7.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    6.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    5.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    7.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    5.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    5.4479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2228    4.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    3.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6518    4.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    3.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    5.8604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2262    5.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    6.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    6.6854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6879    6.7717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3523    6.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372    5.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    4.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    4.5969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    7.3237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0115    6.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    6.9112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7259    6.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    7.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598    7.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    8.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    8.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2388    8.8844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3743    9.4364    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 28 25  1  6  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 41 40  1  1  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 84 86  0  0  0  0  0  0  0  0999 V2000
   -4.9068    0.4765    2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -0.0481    1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750    0.5568   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    1.1648   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456    1.3235   -0.0333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6983    2.6594    0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    3.0789    1.7212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    4.5505    2.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    2.2256    2.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722    0.9757   -0.9135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9053    1.1531   -2.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    2.0660   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0219    3.3514   -0.6436 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3430    4.2944   -1.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2240    5.6789   -1.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1760    3.9790   -2.4455 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403    1.7338    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983    0.6668    0.1083 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0169    0.2111    1.2109 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    0.3024    1.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    0.8489    0.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718   -0.2088    2.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -1.5514    2.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7270   -1.4234    1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5479   -0.4049   -0.6400 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9863   -0.6110   -2.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679   -1.6077    0.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0291   -0.2886   -0.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6762   -1.5649   -0.7356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6945   -1.5297   -1.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174   -2.1958   -2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000   -2.0570   -3.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -2.8996   -3.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -2.2460    0.5017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4971   -2.2522    1.5948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107   -3.7548    0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1243   -4.3405    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827   -4.2362    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -5.1214    1.9360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3084   -3.3942    0.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -2.0642    0.6276 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3449   -1.2788    1.6701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4982   -0.9264    3.1519 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161   -0.0514    3.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5230    1.3328    2.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0153    0.5474   -0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2182    1.5756   -1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    0.6925    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4222    4.7646    2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057    4.8138    2.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7436    5.1484    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0038    1.0040   -3.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013    2.2654   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.6683   -2.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016    2.0242   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    6.3480   -2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108    6.0911   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193    5.6765   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495    2.6557    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.5204    1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    1.1303   -0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834   -0.2855    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8665    0.5284    2.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2412   -1.9215    3.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9557   -2.2904    2.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   -2.0954    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1306   -0.3926    1.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -1.7471    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -1.3891   -2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2740   -2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -1.0363   -2.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -2.1851   -0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169   -0.1812    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119   -2.2534   -1.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -2.5216   -4.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085   -2.5135   -3.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578   -0.9653   -4.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -1.5242    2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -3.9507   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430   -4.2244   -0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -5.4174    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6858   -3.8160    1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0835   -1.6623   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2261   -1.9289    2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 10  1  0
 10 11  1  6
 10 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 34  1  0
 34 35  1  1
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 42  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
 28 25  1  0
 25 26  1  0
 25 27  1  1
 25 18  1  0
  5 10  1  0
 41 34  1  0
 24 66  1  0
 24 67  1  0
 24 68  1  0
 23 64  1  0
 23 65  1  0
 22 62  1  0
 22 63  1  0
 18 61  1  6
 17 59  1  0
 17 60  1  0
 12 55  1  6
 15 56  1  0
 15 57  1  0
 15 58  1  0
 11 52  1  0
 11 53  1  0
 11 54  1  0
 28 73  1  1
 29 74  1  6
 32 75  1  0
 32 76  1  0
 32 77  1  0
 35 78  1  0
 36 79  1  6
 37 80  1  0
 37 81  1  0
 37 82  1  0
 41 83  1  6
 42 84  1  1
  1 44  1  0
  1 45  1  0
  3 46  1  0
  4 47  1  0
  5 48  1  1
  8 49  1  0
  8 50  1  0
  8 51  1  0
 26 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  0
M  END


  Mrv1652309042215532D          

 43 45  0  0  1  0            999 V2000
    0.7818   10.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    9.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738    9.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    8.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    7.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3789    7.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8638    8.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282    9.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    8.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    7.0979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0075    7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    6.6854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6518    7.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    6.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    5.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    7.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    5.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228    5.4479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2228    4.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    3.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6518    4.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    4.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    3.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    5.8604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2262    5.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959    6.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    6.6854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6879    6.7717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3523    6.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372    5.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    4.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017    4.5969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748    7.3237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0115    6.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    6.9112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7259    6.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    7.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598    7.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    8.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    8.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2388    8.8844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3743    9.4364    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 28 25  1  6  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 41 40  1  1  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0195926

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@@]2(C)[C@@H]([C@H](OC(C)=O)[C@]3(O)[C@@H](C)C(=O)O[C@H]3[C@@H](Cl)C(=C)\C=C/[C@@H]2OC(C)=O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H41ClO12/c1-9-10-22(35)42-21-13-20(40-17(5)33)28(7)19(39-16(4)32)12-11-14(2)23(31)25-30(38,15(3)27(36)43-25)26(41-18(6)34)24(28)29(21,8)37/h11-12,15,19-21,23-26,37-38H,2,9-10,13H2,1,3-8H3/b12-11-/t15-,19-,20-,21+,23-,24+,25-,26-,28-,29+,30-/m0/s1

> <INCHI_KEY>
KNEHHUWPBUXWSG-UKOJITJMSA-N

> <FORMULA>
C30H41ClO12

> <MOLECULAR_WEIGHT>
629.1

> <EXACT_MASS>
628.2286545

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.159100126444685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R,17S)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

> <JCHEM_LOGP>
1.5374896126666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.717785944909178

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.347540223072812

> <JCHEM_PKA_STRONGEST_BASIC>
-3.37124216374498

> <JCHEM_POLAR_SURFACE_AREA>
171.95999999999998

> <JCHEM_REFRACTIVITY>
148.9924

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R,17S)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.459  18.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.779  17.354   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.311  17.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.455  16.163   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.776  14.656   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.307  14.495   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.212  15.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.586  17.148   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.744  15.580   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.149  13.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.614  13.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.483  12.480   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.817  13.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.150  12.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.150  10.940   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.484  13.250   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.483  10.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.149  10.170   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.149   8.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.483   7.860   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.483   6.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.817   8.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.150   7.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.150   6.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.816  10.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.289   9.492   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.299  11.207   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.816  12.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.284  12.640   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.658  11.234   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.563   9.988   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.189   8.581   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.936   8.581   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.140  13.671   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.021  12.139   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.194  12.901   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.355  11.369   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.339  13.931   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.845  13.611   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.712  15.338   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.181  15.177   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.446  16.584   0.000  0.00  0.00           C+0
HETATM   43 Cl   UNK     0      -0.699  17.615   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   18   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   10   29                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   36   41                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   34   42                                                  
CONECT   42   41    2   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₁ClO₁₂

Average Mass

629.1000 Da

Monoisotopic Mass

628.22865 Da

IUPAC Name

(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R,17S)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

Traditional Name

(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R,17S)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@@]2(C)[C@@H]([C@H](OC(C)=O)[C@]3(O)[C@@H](C)C(=O)O[C@H]3[C@@H](Cl)C(=C)\C=C/[C@@H]2OC(C)=O)[C@]1(C)O

InChI Identifier

InChI=1S/C30H41ClO12/c1-9-10-22(35)42-21-13-20(40-17(5)33)28(7)19(39-16(4)32)12-11-14(2)23(31)25-30(38,15(3)27(36)43-25)26(41-18(6)34)24(28)29(21,8)37/h11-12,15,19-21,23-26,37-38H,2,9-10,13H2,1,3-8H3/b12-11-/t15-,19-,20-,21+,23-,24+,25-,26-,28-,29+,30-/m0/s1

InChI Key

KNEHHUWPBUXWSG-UKOJITJMSA-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 asbestinum	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

Briarane diterpenoid
Diterpenoid
Diterpene lactone
Pentacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Cyclitol or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
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	1.54	ChemAxon
pKa (Strongest Acidic)	12.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.96 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	148.99 m³·mol⁻¹	ChemAxon
Polarizability	62.16 Å³	ChemAxon
Number of Rings	3	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

10200283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21585460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kobayashi J, Cheng JF, Nakamura H, Ohizumi Y, Tomotake Y, Matsuzaki T, Grace KJ, Jacobs RS, Kato Y, Brinen LS, et al.: Structure and stereochemistry of brianolide, a new antiinflammatory diterpenoid from the Okinawan gorgonian Briareum sp. Experientia. 1991 May 15;47(5):501-2. doi: 10.1007/BF01959955. [PubMed:1675176 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate (NP0195926)

MOL for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

3D MOL for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

3D SDF for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

3D-SDF for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

PDB for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

3D PDB for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

SMILES for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

INCHI for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

Structure for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)

3D Structure for NP0195926 ((1s,2s,3r,4r,7r,8s,10z,12s,13r,14s,16r,17s)-2,12,14-tris(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-10-en-16-yl butanoate)