NP-MRD: Showing NP-Card for methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate (NP0288342)

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Record Information

Version

1.0

Created at

2022-09-09 18:00:21 UTC

Updated at

2022-09-09 18:00:22 UTC

NP-MRD ID

NP0288342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

Description

Methyl shoreate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate is found in Betula platyphylla. It was first documented in 2016 (PMID: 27215130). Based on a literature review very few articles have been published on methyl shoreate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220002D          

 35 38  0  0  1  0            999 V2000
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4263   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.9458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1333   -1.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156   -1.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972   -0.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695   -2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8084    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7388   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0525   -2.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7927   -1.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9980   -2.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -3.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 14 23  1  1  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 87 90  0  0  0  0  0  0  0  0999 V2000
    5.8768   -2.0570   -1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1244   -1.6609   -0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188   -1.6441    1.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -1.4093   -0.2645 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1960   -1.7524   -1.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392   -1.3605   -2.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0133   -0.5832   -1.0583 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4814    0.6645   -1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616   -0.3895    0.2833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8577    0.3129    1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979   -0.4012    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943   -0.6292    0.1808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3709   -1.3624    0.0625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5973   -0.7284    0.6107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5187   -0.5555    2.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8482   -1.5380    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9307   -0.4881    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403    0.7812    0.4251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7679    1.9053   -0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1038    2.2183    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8956    1.5990   -1.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9276    3.0148   -0.2236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754    0.4814   -0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4738   -1.4817   -1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -1.7848   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172   -1.4571   -0.7398 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2172   -2.7588   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -0.0497    0.1743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4845    0.8640   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7579    0.4624    1.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025    1.8182    1.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8644    2.9754    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686    3.6960    0.4296 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222    3.3432    0.9612 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047    4.4575    0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9287   -2.2258   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -2.2242   -2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7160   -0.8937    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4978   -2.6446    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3255   -1.7062    2.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1992   -2.1450    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -2.8870   -1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419   -1.4226   -2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962   -0.7745   -2.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852   -2.2804   -2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5484    0.5181   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    1.5362   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660    0.9789   -2.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -1.4614    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605    0.1479    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    1.3573    1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -1.2421    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000    0.3706    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2936   -2.4152    0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8426   -2.0154   -0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5097   -0.5791    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0433    1.1704    1.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9178    2.7662    1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6046    1.2542    0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6819    2.8455   -0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7688    2.5707   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    0.9410   -2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8963    1.2273   -2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0248    3.6135   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7165   -0.4759   -1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1737   -2.2490   -1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828   -1.3452   -2.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531   -2.8991   -2.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4601   -3.6015   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186   -3.0812   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560   -2.7805    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.6595   -1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347    1.3675   -0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298    0.3335   -1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8827    0.4449    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -0.3100    2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    2.0442    2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1771    1.8567    2.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6818    5.0880   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711    5.0235    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9283    4.1347   -0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 34  1  0
 34 32  1  0
 32 33  2  0
 32 31  1  0
 31 30  1  0
 28 30  1  1
 28 29  1  0
 28  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
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 13 24  1  0
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 13 14  1  0
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 18 23  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
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  4  2  1  0
  2  3  1  0
  2  1  2  3
  9 28  1  0
 26 12  1  0
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 35 85  1  0
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  4 41  1  1
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 13 55  1  1
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 21 69  1  0
 22 70  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  1 36  1  0
  1 37  1  0
M  END


  Mrv1652309092220002D          

 35 38  0  0  1  0            999 V2000
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8307   -0.5732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4263   -1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669    0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.9458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.8156   -1.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972   -0.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6695   -2.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252   -1.2252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8084    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7388   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3669   -1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0525   -2.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7927   -1.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9980   -2.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6837   -3.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 14 23  1  1  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]1CC[C@@H]1[C@H](CC[C@@]21C)[C@]1(C)CC[C@@H](O1)C(C)(C)O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O4/c1-20(2)21-12-18-30(7)24(28(21,5)16-15-26(32)34-9)11-10-22-23(13-17-29(22,30)6)31(8)19-14-25(35-31)27(3,4)33/h21-25,33H,1,10-19H2,2-9H3/t21-,22+,23-,24+,25+,28-,29+,30+,31-/m0/s1

> <INCHI_KEY>
TWFMQZXDUHCZFN-SRACOBAWSA-N

> <FORMULA>
C31H52O4

> <MOLECULAR_WEIGHT>
488.753

> <EXACT_MASS>
488.386560154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.09485839477486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

> <JCHEM_LOGP>
6.179032358333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.325328794365333

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0939011853446026

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
141.10550000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      12.002   1.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.919  -0.683   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.845   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.662  -2.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.685   0.204   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.794  -0.226   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.842  -1.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.116  -2.631   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.389  -3.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.981  -1.358   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.250  -3.905   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.607  -2.287   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.242   2.392   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.846  -2.127   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.120  -1.444   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.018  -2.980   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.298  -3.837   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.680  -3.156   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      11.196  -5.373   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.476  -6.230   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   18   14                                                       
CONECT   24   13   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12    7   27                                             
CONECT   27   26                                                            
CONECT   28    9    4   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl shoreic acid	Generator

Chemical Formula

C₃₁H₅₂O₄

Average Mass

488.7530 Da

Monoisotopic Mass

488.38656 Da

IUPAC Name

methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

Traditional Name

methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]1CC[C@@H]1[C@H](CC[C@@]21C)[C@]1(C)CC[C@@H](O1)C(C)(C)O)C(C)=C

InChI Identifier

InChI=1S/C31H52O4/c1-20(2)21-12-18-30(7)24(28(21,5)16-15-26(32)34-9)11-10-22-23(13-17-29(22,30)6)31(8)19-14-25(35-31)27(3,4)33/h21-25,33H,1,10-19H2,2-9H3/t21-,22+,23-,24+,25+,28-,29+,30+,31-/m0/s1

InChI Key

TWFMQZXDUHCZFN-SRACOBAWSA-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
Betula platyphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Seco-podocarpan diterpenoid
Fatty acid ester
Fatty acyl
Methyl ester
Tertiary alcohol
Oxolane
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.18	ChemAxon
pKa (Strongest Acidic)	14.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.11 m³·mol⁻¹	ChemAxon
Polarizability	59.09 Å³	ChemAxon
Number of Rings	4	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

23281687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44421646

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang J, Xu J, Zhang J, Liu WY, Xie N, Chen L, Feng F, Qu W: Novel tirucallane triterpenoids from the stem bark of Toona sinensis. Fitoterapia. 2016 Jul;112:97-103. doi: 10.1016/j.fitote.2016.05.009. Epub 2016 May 20. [PubMed:27215130 ]
LOTUS database [Link]

Showing NP-Card for methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate (NP0288342)

MOL for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D MOL for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D SDF for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D-SDF for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

PDB for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D PDB for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

SMILES for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

INCHI for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

Structure for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D Structure for NP0288342 (methyl 3-[(3s,3ar,5ar,6s,7s,9ar,9br)-3-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)