NP-MRD: Showing NP-Card for Isolinaritriol triacetate (NP0066162)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 10:19:29 UTC

Updated at

2022-04-28 10:19:29 UTC

NP-MRD ID

NP0066162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isolinaritriol triacetate

Description

(2R)-1-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-5-(acetyloxy)-3-[(acetyloxy)methyl]pent-3-en-2-yl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Isolinaritriol triacetate is found in Linaria saxatilis. Based on a literature review very few articles have been published on (2R)-1-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-5-(acetyloxy)-3-[(acetyloxy)methyl]pent-3-en-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212192D          

 32 33  0  0  1  0            999 V2000
   -4.0125    0.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3998    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9626   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3499   -1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7508    0.3159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1880    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    0.3447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4891   -0.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8764   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009   -1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2118    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    2.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    3.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    4.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    4.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    5.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    5.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    2.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    3.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    4.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552    3.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    4.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5254   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
  9 12  1  6  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 14 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  8 31  1  6  0  0  0
  5 32  1  6  0  0  0
M  END

     RDKit          3D

 72 73  0  0  0  0  0  0  0  0999 V2000
   -3.1420    3.3741   -2.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.1643   -2.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    1.4968   -3.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765    0.0361   -3.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.6898   -1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9421    0.3176   -0.8399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6577   -0.3628    0.4502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5672   -1.6386    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992   -1.0065    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -0.2040    0.6762 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0611    0.6103    1.7832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3748    1.9673    1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5790    2.8683    2.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    2.4043    0.4242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797   -1.0142    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247   -2.2171    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -3.0746   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5352   -3.3526   -1.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6206   -4.0815   -1.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775   -4.3574   -3.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4724   -4.4567   -1.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -0.3399    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3256   -0.0708    2.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    0.5131    3.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0550    0.7693    4.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3782    0.8521    2.6144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0442    0.4553    1.6222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2418   -0.0657    2.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502    1.9087    1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9555    2.3707    0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795    1.3583   -0.8828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3986    0.8780   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590    3.8569   -3.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6562    4.0393   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201    1.7539   -3.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2591    1.9054   -4.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592   -0.3755   -3.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0961   -0.1351   -3.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.5034   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263   -1.1873   -1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750    0.8052   -1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108   -2.2830    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264   -2.2725   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923   -1.3707    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -1.6147   -0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -1.7749    1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    0.4591   -0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165    3.3118    2.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    3.6954    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    2.2875    3.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -2.7058   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3679   -2.7071    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614   -4.0775    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -3.4380   -4.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -4.9212   -3.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834   -4.9671   -3.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4868    0.6212    0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3619   -0.8646    0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6638    0.0715    5.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    1.8415    4.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9773    0.6977    4.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    0.3999    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827    0.3224    1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.4421    3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -1.1198    2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730    2.2667    2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237    2.5243    1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    3.3175   -0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9790    2.8097    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8372    0.2877   -0.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543    0.3843   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0491    1.8047   -1.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10 15  1  0
 15 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  7 27  1  0
  2 31  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 27 62  1  1
 29 66  1  0
 29 67  1  0
 30 68  1  0
 30 69  1  0
 32 70  1  0
 32 71  1  0
 32 72  1  0
  6 41  1  6
  5 39  1  0
  5 40  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  1 33  1  0
  1 34  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 13 48  1  0
 13 49  1  0
 13 50  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
M  END


  Mrv1652304282212192D          

 32 33  0  0  1  0            999 V2000
   -4.0125    0.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3998    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9626   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3499   -1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7508    0.3159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1880    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    0.3447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4891   -0.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8764   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009   -1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    1.5822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2118    2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    2.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    3.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    4.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    4.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    5.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    5.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    2.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    3.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    4.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552    3.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    4.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316    1.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5254   -1.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
  9 12  1  6  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 14 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  8 31  1  6  0  0  0
  5 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)[C@H](CCCC2=C)[C@@]1(C)C[C@@H](OC(C)=O)C(\COC(C)=O)=C\COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O6/c1-17-9-8-10-24-25(17,6)13-11-18(2)26(24,7)15-23(32-21(5)29)22(16-31-20(4)28)12-14-30-19(3)27/h12,18,23-24H,1,8-11,13-16H2,2-7H3/b22-12+/t18-,23-,24+,25+,26+/m1/s1

> <INCHI_KEY>
QZVBOHJQUQFCGN-LKYLEVJKSA-N

> <FORMULA>
C26H40O6

> <MOLECULAR_WEIGHT>
448.6

> <EXACT_MASS>
448.282489008

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.1151580094333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4R)-5-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-4-(acetyloxy)-3-[(acetyloxy)methyl]pent-2-en-1-yl acetate

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
3.971104453666666

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.53076107186749

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
122.79849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4R)-5-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]-4-(acetyloxy)-3-[(acetyloxy)methyl]pent-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -7.490   1.842   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.213   0.482   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.397  -0.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.120  -2.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.858  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.135   0.590   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.951   1.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.596   0.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.780  -0.663   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.503  -2.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.042  -2.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.241  -0.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.596   2.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.262   2.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.262   4.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.928   5.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.928   6.803   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.262   7.573   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.262   9.113   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.596   9.883   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.928   9.883   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.596   5.263   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.596   6.803   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.929   7.573   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.263   6.803   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.929   9.113   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.928   2.183   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.405   2.953   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.405   4.493   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.739   2.183   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.319   1.505   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.581  -2.130   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11   32                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   13   31                                             
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   14   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    8                                                            
CONECT   32    5                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(2R)-1-[(1S,2R,4AR,8ar)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-5-(acetyloxy)-3-[(acetyloxy)methyl]pent-3-en-2-yl acetic acid	Generator

Chemical Formula

C₂₆H₄₀O₆

Average Mass

448.6000 Da

Monoisotopic Mass

448.28249 Da

IUPAC Name

(2E,4R)-5-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-4-(acetyloxy)-3-[(acetyloxy)methyl]pent-2-en-1-yl acetate

Traditional Name

(2E,4R)-5-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]-4-(acetyloxy)-3-[(acetyloxy)methyl]pent-2-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)[C@H](CCCC2=C)[C@@]1(C)C[C@@H](OC(C)=O)C(\COC(C)=O)=C\COC(C)=O

InChI Identifier

InChI=1S/C26H40O6/c1-17-9-8-10-24-25(17,6)13-11-18(2)26(24,7)15-23(32-21(5)29)22(16-31-20(4)28)12-14-30-19(3)27/h12,18,23-24H,1,8-11,13-16H2,2-7H3/b22-12+/t18-,23-,24+,25+,26+/m1/s1

InChI Key

QZVBOHJQUQFCGN-LKYLEVJKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Linaria saxatilis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Tricarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.33	ALOGPS
logP	3.97	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	122.8 m³·mol⁻¹	ChemAxon
Polarizability	50.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10311570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21724985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isolinaritriol triacetate (NP0066162)

MOL for NP0066162 (Isolinaritriol triacetate)

3D MOL for NP0066162 (Isolinaritriol triacetate)

3D SDF for NP0066162 (Isolinaritriol triacetate)

3D-SDF for NP0066162 (Isolinaritriol triacetate)

PDB for NP0066162 (Isolinaritriol triacetate)

3D PDB for NP0066162 (Isolinaritriol triacetate)

SMILES for NP0066162 (Isolinaritriol triacetate)

INCHI for NP0066162 (Isolinaritriol triacetate)

Structure for NP0066162 (Isolinaritriol triacetate)

3D Structure for NP0066162 (Isolinaritriol triacetate)