NP-MRD: Showing NP-Card for 1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate (NP0203560)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 23:03:14 UTC

Updated at

2022-09-04 23:03:15 UTC

NP-MRD ID

NP0203560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate

Description

1-(5-{5-[(Acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate is found in Acamptopappus sphaerocephalus. 1-(5-{5-[(Acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505472D          

 33 34  0  0  0  0            999 V2000
    9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2874    0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3480    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1604    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6907    0.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4426   -0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    1.6500    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  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 33  1  0  0  0  0
M  END

     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
    9.1961    0.4371    0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2062   -0.3188    0.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5176   -1.0864   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7362   -1.0617   -1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5243   -1.9015   -1.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1601   -1.7180   -1.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7730   -0.2863   -1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5382    0.5559   -1.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5680    0.1682   -0.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354    1.4951   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499    1.8464   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    0.9884    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009   -0.4083    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647    1.6259    1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276    1.2622    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -0.0829    0.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1869   -0.4001    2.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517   -1.1954    2.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    0.0122    2.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    0.7512    1.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    0.0570    0.3474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1928   -0.3997   -0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2068   -1.9481   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671   -0.0982   -1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5423    1.1495   -2.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118    1.8483   -1.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3781    0.8558   -0.5350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2616    1.7278    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1639    0.0170   -1.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9630   -0.9207   -0.9595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1123   -0.9553   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6811   -2.2740    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7136    0.0967    0.0228 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1294    1.4781    0.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8746    0.4617    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2038    0.0209    0.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4795   -1.5359   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -2.9504   -1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4175   -2.2998   -1.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618   -2.0553   -0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1985    1.7757   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0381    2.1416   -0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067    2.9187   -0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893   -1.0312    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877   -0.9106   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5138   -0.5261    1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    1.5017    2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0385    2.7593    0.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3030    1.5361   -0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1428    2.0790    0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1289   -0.8001    0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440   -2.1185    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -0.5815    3.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -1.4977    3.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5271   -0.2237    3.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    1.8255    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3054    0.5994    2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127   -0.8567    0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -2.3436   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3830   -2.2766    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9352   -2.3598   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436   -0.0625   -1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2410   -0.9612   -2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.8347   -2.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018    0.9089   -3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2550    2.4678   -1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050    2.4947   -0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0833    2.1551   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7305    1.2584    1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7117    2.6743    0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8385    0.7879   -2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379   -0.3305   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9940   -2.7724    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004   -2.9077   -0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6791   -2.1168    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  6
 22 16  1  0
 22 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  6
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  1
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
 26 66  1  0
 26 67  1  0
 25 64  1  0
 25 65  1  0
 24 62  1  0
 24 63  1  0
 23 59  1  0
 23 60  1  0
 23 61  1  0
M  END


  Mrv1533004251505472D          

 33 34  0  0  0  0            999 V2000
    9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2874    0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3480    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1604    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6907    0.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4426   -0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473    1.6500    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  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC(=O)OCC=C(C)CCC1C(C)=CCC2C(C)(COC(C)=O)CCCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-19(14-17-32-25(30)13-12-24(29)31-6)8-10-22-20(2)9-11-23-26(4,18-33-21(3)28)15-7-16-27(22,23)5/h9,14,22-23H,7-8,10-13,15-18H2,1-6H3

> <INCHI_KEY>
JBKOFQXECNQYPG-UHFFFAOYSA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.02120552497934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
4.673613242999998

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.546935100444113

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
128.86639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      18.672   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      20.005   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.005   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.673   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.006  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      25.340   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      26.674   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.007   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.341   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.675   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.008   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.342   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.342   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.676   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.009   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.009   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.343   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.870   1.447   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.860  -0.267   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      39.850   0.912   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      41.366   0.645   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      42.356   1.825   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      41.893  -0.802   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.343  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      36.009  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.676  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      34.676   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.342  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      32.008   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   23   28                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   16   20   32                                             
CONECT   32   31                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioic acid	Generator

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate

Traditional Name

1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(=O)OCC=C(C)CCC1C(C)=CCC2C(C)(COC(C)=O)CCCC12C

InChI Identifier

InChI=1S/C27H42O6/c1-19(14-17-32-25(30)13-12-24(29)31-6)8-10-22-20(2)9-11-23-26(4,18-33-21(3)28)15-7-16-27(22,23)5/h9,14,22-23H,7-8,10-13,15-18H2,1-6H3

InChI Key

JBKOFQXECNQYPG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acamptopappus sphaerocephalus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Tricarboxylic acid or derivatives
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Methyl ester
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	6.05	ALOGPS
logP	4.67	ChemAxon
logS	-5.8	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	13	ChemAxon
Refractivity	128.87 m³·mol⁻¹	ChemAxon
Polarizability	53.02 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate (NP0203560)

MOL for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

3D MOL for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

3D SDF for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

3D-SDF for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

PDB for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

3D PDB for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

SMILES for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

INCHI for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

Structure for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)

3D Structure for NP0203560 (1-(5-{5-[(acetyloxy)methyl]-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl}-3-methylpent-2-en-1-yl) 4-methyl butanedioate)