NP-MRD: Showing NP-Card for Methyl 15-cinnamoyloxy-7-labden-17-oate (NP0066092)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 10:15:27 UTC

Updated at

2022-04-28 10:15:28 UTC

NP-MRD ID

NP0066092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl 15-cinnamoyloxy-7-labden-17-oate

Description

Methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Methyl 15-cinnamoyloxy-7-labden-17-oate is found in Halimium viscosum. Based on a literature review very few articles have been published on methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212152D          

 34 36  0  0  1  0            999 V2000
   -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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3848    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  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
   -2.1434   -0.4125    0.0000 C   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
    0.7145   -0.4125    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
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    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
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    0.7145    2.0625    0.0000 C   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
   -3.8545    0.4623    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  1  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
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  6  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  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 18 32  1  1  0  0  0
  6 33  1  1  0  0  0
  3 34  1  0  0  0  0
M  END

     RDKit          3D

 76 78  0  0  0  0  0  0  0  0999 V2000
   -1.5989   -4.0076   -3.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511   -2.9000   -2.6071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0427   -2.2259   -2.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -2.6088   -3.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179   -1.0884   -1.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4167   -0.4619   -1.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5714    0.6882   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    0.1641    0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6997    0.9956    1.6846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6158    0.1334    2.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7407    1.9420    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272    1.7668    2.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    1.5234    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003    1.0555    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -0.1172    0.5881 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2826   -1.2971    1.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2092   -0.4954   -0.7871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4063    0.5859   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845    0.1265   -2.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5276   -0.8096   -2.3045 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2363   -1.1827   -3.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6232   -0.0660   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.1362   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -0.6430   -0.4992 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    0.3796   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802    0.9308   -2.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7267    0.8657   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033    0.3248    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    0.7420    1.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9617    1.7498    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9966    2.0978    2.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1694    1.4470    3.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2994    0.4333    4.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2809    0.1005    3.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -3.7311   -4.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -4.8090   -2.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724   -4.4359   -3.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1789   -0.8274   -2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6962    0.8476   -0.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214    1.6132   -1.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6144   -0.8762    0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3140   -0.4572    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0098   -0.5534    3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2027    0.8410    3.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3325    2.5617    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9484    2.6702    1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6988    1.4543    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737    2.8701    2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529    1.7017    3.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0947    0.7612    3.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    2.4319    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133    1.8890    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367    0.7353    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1852   -1.4122    1.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4827   -1.1142    2.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7368   -2.2284    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -1.3350   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9527    1.4586   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.9902   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480   -0.2764   -3.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    1.0303   -3.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2810   -1.6674   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -1.1237   -4.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442   -2.2627   -3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -0.5197   -3.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430    0.2471   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0406    0.7395   -2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269   -1.9825   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677   -1.5495   -2.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534    1.6672   -0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3356   -0.4963    1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8712    2.2924    0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6783    2.8907    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792    1.7273    4.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -0.0675    4.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -0.7079    3.4023 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 17  5  1  0
 34 29  1  0
 15  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  1
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  1
 21 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  0
 23 69  1  0
 27 70  1  0
 28 71  1  0
 30 72  1  0
 31 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  0
M  END


  Mrv1652304282212152D          

 34 36  0  0  1  0            999 V2000
   -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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3848    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  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
   -2.1434   -0.4125    0.0000 C   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
    0.7145   -0.4125    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
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    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
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    0.7145    2.0625    0.0000 C   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
   -3.8545    0.4623    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  1  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
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  6  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  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 18 32  1  1  0  0  0
  6 33  1  1  0  0  0
  3 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC[C@@H]2C(C)(C)CCC[C@]2(C)[C@@H]1CC[C@@H](C)CCOC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O4/c1-22(18-21-34-27(31)17-13-23-10-7-6-8-11-23)12-15-25-24(28(32)33-5)14-16-26-29(2,3)19-9-20-30(25,26)4/h6-8,10-11,13-14,17,22,25-26H,9,12,15-16,18-21H2,1-5H3/b17-13+/t22-,25-,26-,30-/m1/s1

> <INCHI_KEY>
PTBIPOPCPDBHRO-NXQNVXAXSA-N

> <FORMULA>
C30H42O4

> <MOLECULAR_WEIGHT>
466.662

> <EXACT_MASS>
466.308309832

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.3891952216846

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

> <ALOGPS_LOGP>
7.48

> <JCHEM_LOGP>
7.955859503666665

> <ALOGPS_LOGS>
-6.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.530293588114231

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
138.48430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.81e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

> <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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.185   2.577   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.195   0.863   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5   34                                             
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8   33                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    8   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   18                                                            
CONECT   33    6                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,4ar,8as)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid	Generator

Chemical Formula

C₃₀H₄₂O₄

Average Mass

466.6620 Da

Monoisotopic Mass

466.30831 Da

IUPAC Name

methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

Traditional Name

methyl (1S,4aR,8aS)-5,5,8a-trimethyl-1-[(3R)-3-methyl-5-{[(2E)-3-phenylprop-2-enoyl]oxy}pentyl]-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC[C@@H]2C(C)(C)CCC[C@]2(C)[C@@H]1CC[C@@H](C)CCOC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H42O4/c1-22(18-21-34-27(31)17-13-23-10-7-6-8-11-23)12-15-25-24(28(32)33-5)14-16-26-29(2,3)19-9-20-30(25,26)4/h6-8,10-11,13-14,17,22,25-26H,9,12,15-16,18-21H2,1-5H3/b17-13+/t22-,25-,26-,30-/m1/s1

InChI Key

PTBIPOPCPDBHRO-NXQNVXAXSA-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
Halimium viscosum	Plant	KNApSAcK

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
Cinnamic acid ester
Cinnamic acid or derivatives
Styrene
Fatty acid ester
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.48	ALOGPS
logP	7.96	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.48 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

163105570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methyl 15-cinnamoyloxy-7-labden-17-oate (NP0066092)

MOL for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

3D MOL for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

3D SDF for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

3D-SDF for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

PDB for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

3D PDB for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

SMILES for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

INCHI for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

Structure for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)

3D Structure for NP0066092 (Methyl 15-cinnamoyloxy-7-labden-17-oate)