NP-MRD: Showing NP-Card for 4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate (NP0231095)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 11:47:01 UTC

Updated at

2022-09-06 11:47:01 UTC

NP-MRD ID

NP0231095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate

Description

4A,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-decahydronaphthalen-1-yl benzoate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review very few articles have been published on 4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-decahydronaphthalen-1-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213472D          

 36 38  0  0  0  0            999 V2000
   -0.1960   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    1.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
   -4.9093   -2.1933   -2.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503   -2.0919   -0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994   -2.7272    0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633   -1.2996   -0.6420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977   -1.0867    0.5352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4148   -0.5820    1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -2.4775    0.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669   -2.8362    0.3689 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0244   -3.7471    1.2798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -1.7517    0.0107 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4435   -1.4675   -1.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465   -0.4562    0.7815 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2890   -0.7914    2.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765    0.1781    3.1486 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0619    0.5770    0.3589 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1621   -0.0593   -0.2857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484   -0.0855    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.4964    1.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617   -0.7421   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983   -1.3712   -1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4854   -1.9731   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534   -1.9665   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9022   -1.3270   -0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.7190    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    1.7348   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    2.3111    0.1387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5345    3.5756    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    3.5118    2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0779    4.6076   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8085    4.0573    1.2373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917    1.2961    0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.0838    0.3220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2055    0.1385   -1.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2183    0.6882   -1.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793    0.8912   -3.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131    1.0465   -1.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1899   -2.3743   -2.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820   -1.2550   -2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6775   -3.0047   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093    0.0610    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1630    0.0959    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813   -1.4123    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0971   -2.7118    1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5770   -3.2892    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -3.4684   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -4.2910    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -1.9854    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -1.9474   -1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.9386    2.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0396   -1.7998    2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973   -0.1310    3.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993    1.0010    1.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -1.3752   -2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3656   -2.4679   -3.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6097   -2.4446   -2.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8774   -1.3000    0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -0.2298    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3316    2.5584   -0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    1.5803   -1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    2.7001   -0.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875    3.3272    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356    2.9051    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524    4.5673    2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1536    4.7132    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3798    5.6006    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819    4.3146   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593    3.8255    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6380    1.6295    0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.4349    1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3696    0.1747   -3.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    1.9474   -3.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653    0.7153   -3.8003 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
  5  4  1  6
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  1
 13 14  1  0
 12 15  1  0
 15 25  1  0
 25 26  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  6
 33 34  1  0
 34 35  1  0
 34 36  2  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 32  5  1  0
 24 19  1  0
 32 12  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  6 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
 10 47  1  1
 11 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 15 52  1  1
 25 58  1  0
 25 59  1  0
 26 60  1  6
 31 68  1  0
 31 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
M  END


  Mrv1652309062213472D          

 36 38  0  0  0  0            999 V2000
   -0.1960   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    1.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0231095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)CC(O)C(O)C2(CO)C(CC(CC12OC(C)=O)C(C)(C)O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O10/c1-15(28)35-24(5)13-19(30)21(31)25(14-27)20(34-22(32)17-9-7-6-8-10-17)11-18(23(3,4)33)12-26(24,25)36-16(2)29/h6-10,18-21,27,30-31,33H,11-14H2,1-5H3

> <INCHI_KEY>
SGJICULKIRHGJX-UHFFFAOYSA-N

> <FORMULA>
C26H36O10

> <MOLECULAR_WEIGHT>
508.564

> <EXACT_MASS>
508.230847359

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.94597194707603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-decahydronaphthalen-1-yl benzoate

> <JCHEM_LOGP>
0.12618769466666604

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.540942363301586

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.385473477851942

> <JCHEM_PKA_STRONGEST_BASIC>
-2.772954025981913

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
125.8118

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1H-naphthalen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.366  -2.545   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.161  -3.992   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.829  -5.172   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.677  -4.260   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.375   2.177   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.772  -1.746   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   32                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15   32                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   15   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   26   32                                                       
CONECT   32   31    5   12   33                                             
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
4a,5-Bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-decahydronaphthalen-1-yl benzoic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₀

Average Mass

508.5640 Da

Monoisotopic Mass

508.23085 Da

IUPAC Name

4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-decahydronaphthalen-1-yl benzoate

Traditional Name

4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1H-naphthalen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)CC(O)C(O)C2(CO)C(CC(CC12OC(C)=O)C(C)(C)O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H36O10/c1-15(28)35-24(5)13-19(30)21(31)25(14-27)20(34-22(32)17-9-7-6-8-10-17)11-18(23(3,4)33)12-26(24,25)36-16(2)29/h6-10,18-21,27,30-31,33H,11-14H2,1-5H3

InChI Key

SGJICULKIRHGJX-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Cyclitol or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	0.13	ChemAxon
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.81 m³·mol⁻¹	ChemAxon
Polarizability	51.95 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

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

162857139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate (NP0231095)

MOL for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

3D MOL for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

3D SDF for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

3D-SDF for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

PDB for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

3D PDB for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

SMILES for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

INCHI for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

Structure for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)

3D Structure for NP0231095 (4a,5-bis(acetyloxy)-7,8-dihydroxy-8a-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-5-methyl-hexahydro-1h-naphthalen-1-yl benzoate)