NP-MRD: Showing NP-Card for methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate (NP0228852)

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Record Information

Version

2.0

Created at

2022-09-06 08:40:19 UTC

Updated at

2022-09-06 08:40:19 UTC

NP-MRD ID

NP0228852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate

Description

Viburnol I belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate is found in Viburnum dilatatum. Based on a literature review very few articles have been published on Viburnol I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210402D          

 38 41  0  0  1  0            999 V2000
   -3.4007    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7876    2.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030    1.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314    1.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3899    2.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5614    3.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    2.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4329    1.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3491   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6040   -1.0396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8194   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590   -1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -2.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5619   -3.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -4.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029   -3.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6799    1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4561    1.2515    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  1  0  0  0
 16 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 15 37  1  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END

     RDKit          3D

 86 89  0  0  0  0  0  0  0  0999 V2000
   -9.3340    1.3687   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9333    1.5662   -0.8007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424    0.6223   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7225   -0.3958    0.3262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6963    0.7206   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1999    1.7306   -0.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212   -0.2770    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2099   -0.1988    2.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3270   -1.6269    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140    0.0165    0.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1957   -0.0680   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -0.5255   -1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972   -0.5325   -0.8993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0376   -1.8823   -0.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -0.0593    0.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0556   -0.2137    1.5057 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1013    0.7119    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    0.3972   -0.2793 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5061    1.2259   -0.9561 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8980    1.2313   -0.4309 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9999    1.7640    0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684    2.0615   -1.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -0.1358   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266   -0.0782    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4068    1.0257    0.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7513   -1.2691    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9701   -1.1624    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7824   -2.4247    0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6012    0.1162    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4466    0.7391   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9912    0.2928   -2.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3490    0.5080   -1.3012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1879    1.9197   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175    0.1804    2.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -0.0170    2.4320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6492    1.2653    2.5521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3197   -0.6093    1.0611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3407   -2.0910    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5308    0.5839   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8962    2.2851   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6226    0.8705    0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674   -0.6113    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6616   -0.8276    2.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507    0.8485    2.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470   -2.3426   -0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0812   -2.0627    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -1.5152   -0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3037    1.1220    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3789    0.9375   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0434   -0.6845   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237    0.0382   -2.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0631   -1.5711   -2.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -2.3680    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -2.5878   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230   -1.9180   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678    1.0558    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -1.1946    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418    0.3921    1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658    1.7407    1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8808   -0.6572   -0.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2035    2.3135   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2494    0.9650    1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8474    2.5192    1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227    2.3610    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    2.9683   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -0.6996   -1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9711   -0.7426    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3781   -2.2445   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9226   -2.8781   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7194   -2.2264    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1700   -3.0865    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6477   -0.0772    1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0961    0.6024    1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7154    0.8365    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -0.1193   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    1.5425   -3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.0285   -3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221   -0.6682   -3.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    1.9997   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    2.5380   -2.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300    2.4633   -0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -0.6905    3.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0983    1.2917    3.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -2.6715    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401   -2.3614    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1836   -2.3940    1.8242 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
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  6
 19 20  1  0
 20 21  1  0
 20 22  1  6
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  3
 27 28  1  0
 27 29  1  0
 16 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  1
 37 10  1  0
 32 13  1  0
 37 15  1  0
 32 18  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  1
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  6
 16 57  1  1
 17 58  1  0
 17 59  1  0
 18 60  1  1
 19 61  1  6
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 26 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 35 82  1  1
 36 83  1  0
 38 84  1  0
 38 85  1  0
 38 86  1  0
M  END


  Mrv1652309062210402D          

 38 41  0  0  1  0            999 V2000
   -3.4007    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7876    2.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030    1.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314    1.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3899    2.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5614    3.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    2.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4329    1.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3491   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6040   -1.0396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8194   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886   -0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590   -1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3069   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -2.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5619   -3.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -3.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -4.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029   -3.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6799    1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4561    1.2515    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  1  0  0  0
 16 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 15 37  1  0  0  0  0
 10 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0228852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=O)C(C)(C)[C@@H]1CC[C@]2(C)[C@@H]3[C@@H](C[C@@H]4[C@H](CC[C@@]24C)[C@](C)(O)CC(=O)C=C(C)C)O[C@@H](O)[C@@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O7/c1-17(2)14-18(32)16-30(7,36)19-10-12-28(5)20(19)15-21-23-29(28,6)13-11-22(31(23,8)26(35)38-21)27(3,4)24(33)25(34)37-9/h14,19-23,26,35-36H,10-13,15-16H2,1-9H3/t19-,20+,21+,22-,23-,26+,28+,29+,30+,31-/m0/s1

> <INCHI_KEY>
UDYWWYJDKQTVSC-YVFXTZONSA-N

> <FORMULA>
C31H48O7

> <MOLECULAR_WEIGHT>
532.718

> <EXACT_MASS>
532.340003886

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.59920195317544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-[(1R,2R,5S,6R,8R,10R,11S,12R,15S)-10-hydroxy-5-[(2R)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadecan-12-yl]-3-methyl-2-oxobutanoate

> <JCHEM_LOGP>
5.495189120666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.58141716131452

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.939122399056355

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98205313437464

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
144.51250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(1R,2R,5S,6R,8R,10R,11S,12R,15S)-10-hydroxy-5-[(2R)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadecan-12-yl]-3-methyl-2-oxobutanoate

> <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      -6.348   2.889   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.204   3.919   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.739   3.444   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.419   1.937   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.594   4.474   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.915   5.980   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.130   3.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.606   2.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.654   5.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.541   3.431   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.252  -0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.727  -1.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.263  -2.416   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.192  -1.465   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.203  -3.405   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.173  -4.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.667  -4.229   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.649  -6.014   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.618  -7.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.094  -8.623   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.112  -6.838   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.157   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.252   2.016   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.002   3.065   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.851   2.336   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13   16   37                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   19   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   18   13   33                                             
CONECT   33   32                                                            
CONECT   34   16   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   15   10   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈O₇

Average Mass

532.7180 Da

Monoisotopic Mass

532.34000 Da

IUPAC Name

methyl 3-[(1R,2R,5S,6R,8R,10R,11S,12R,15S)-10-hydroxy-5-[(2R)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0^{2,6}.0^{11,15}]pentadecan-12-yl]-3-methyl-2-oxobutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C(=O)C(C)(C)[C@@H]1CC[C@]2(C)[C@@H]3[C@@H](C[C@@H]4[C@H](CC[C@@]24C)[C@](C)(O)CC(=O)C=C(C)C)O[C@@H](O)[C@@]13C

InChI Identifier

InChI=1S/C31H48O7/c1-17(2)14-18(32)16-30(7,36)19-10-12-28(5)20(19)15-21-23-29(28,6)13-11-22(31(23,8)26(35)38-21)27(3,4)24(33)25(34)37-9/h14,19-23,26,35-36H,10-13,15-16H2,1-9H3/t19-,20+,21+,22-,23-,26+,28+,29+,30+,31-/m0/s1

InChI Key

UDYWWYJDKQTVSC-YVFXTZONSA-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
Viburnum dilatatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Fatty acid ester
Alpha-keto acid
Beta-hydroxy ketone
Fatty acyl
Keto acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Hemiacetal
Ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
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	5.5	ChemAxon
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	144.51 m³·mol⁻¹	ChemAxon
Polarizability	60.6 Å³	ChemAxon
Number of Rings	4	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

C00058796

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

15329757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate (NP0228852)

MOL for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

3D MOL for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

3D SDF for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

3D-SDF for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

PDB for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

3D PDB for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

SMILES for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

INCHI for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

Structure for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)

3D Structure for NP0228852 (methyl 3-[(1r,2r,5s,6r,8r,10r,11s,12r,15s)-10-hydroxy-5-[(2r)-2-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-1,2,11-trimethyl-9-oxatetracyclo[6.6.1.0²,⁶.0¹¹,¹⁵]pentadecan-12-yl]-3-methyl-2-oxobutanoate)