NP-MRD: Showing NP-Card for Foliamenthin (NP0057644)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 03:02:56 UTC

Updated at

2022-04-28 03:02:56 UTC

NP-MRD ID

NP0057644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Foliamenthin

Description

(3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Foliamenthin is found in Menyanthes trifoliata . Based on a literature review very few articles have been published on (3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205032D          

 38 40  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  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
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 10 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  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
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 19 22  1  6  0  0  0
 18 23  1  1  0  0  0
 17 24  1  1  0  0  0
 24 25  1  0  0  0  0
  4 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 33 37  1  0  0  0  0
 29 38  1  0  0  0  0
M  END

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
   -4.6413   -2.7547   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -2.7650    0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900   -1.8313    0.6370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6585   -0.8567   -0.4857 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8335   -0.1553   -0.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7153    1.2062   -0.3266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3771    1.5673    0.8532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7557    1.4169    0.7232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3569    1.2788    2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7651    0.1330    2.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2977    2.5573   -0.0720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5234    3.6273    0.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3161    2.9577   -1.1256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0298    3.3229   -2.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3795    1.8429   -1.5330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0469    0.8948   -2.3103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -1.4972   -1.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -2.4651   -1.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536   -3.0107   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -3.9989   -0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -4.5965   -1.9968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529   -4.1458    0.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0696   -2.9631    1.0562 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1467   -2.2429    0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577   -2.0590    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865   -2.5524    2.2267 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4772   -1.3121    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170   -1.1786    1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3822   -0.7937   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110   -0.0476   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    0.5290   -1.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876    1.5851   -0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420    2.8207   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5510    1.4854    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7724    2.4713    1.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0172    3.6007    1.6723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495   -2.1329    1.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -2.6910    0.5586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6813   -2.0762   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4828   -3.4837   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224   -3.5330    1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550   -1.2870    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.0906   -0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    1.5746   -0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9121    0.4279    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    2.1509    2.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4549    1.1131    2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4149   -0.3815    3.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716    2.1969   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4485    3.5708    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    3.8353   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8875    3.7075   -1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835    2.2753   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358    0.4366   -2.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1632   -2.7478   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344   -3.2954    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6260   -0.2066    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -1.2321    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142   -1.9515    2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.0121   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811    0.7845   -2.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3370   -0.7337   -2.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8675    1.0646   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3039   -0.2508   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4622    3.7242   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    2.8054   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2117    2.8738    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1717    0.5570    0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8461    2.7938    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6927    1.9399    2.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9404    3.9864    2.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098   -2.0381    2.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253   -1.0773    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5978   -3.6676    1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  2  0
 27 28  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  1  0
 23 37  1  0
 37 38  1  0
 38  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 32 34  2  0
 34 35  1  0
 35 36  1  0
 22 23  1  0
 19 38  1  0
 15  6  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
 31 63  1  0
 31 64  1  0
 30 61  1  0
 30 62  1  0
 29 60  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 23 56  1  1
 37 72  1  0
 37 73  1  0
 38 74  1  1
  3 42  1  1
  2 41  1  0
  1 39  1  0
  1 40  1  0
  4 43  1  1
  6 44  1  1
  8 45  1  6
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  6
 12 50  1  0
 13 51  1  1
 14 52  1  0
 15 53  1  6
 16 54  1  0
 18 55  1  0
 34 68  1  0
 35 69  1  0
 35 70  1  0
 36 71  1  0
M  END


  Mrv1652304282205032D          

 38 40  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  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
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 10 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  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
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 19 22  1  6  0  0  0
 18 23  1  1  0  0  0
 17 24  1  1  0  0  0
 24 25  1  0  0  0  0
  4 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 33 37  1  0  0  0  0
 29 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC\C=C(/C)C(=O)O[C@H]1C[C@H]2[C@H](C=C)[C@H](O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)OC=C2C(=O)O1)=C/CO

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O12/c1-4-15-16-10-19(36-23(32)14(3)7-5-6-13(2)8-9-27)37-24(33)17(16)12-34-25(15)38-26-22(31)21(30)20(29)18(11-28)35-26/h4,7-8,12,15-16,18-22,25-31H,1,5-6,9-11H2,2-3H3/b13-8+,14-7+/t15-,16-,18-,19+,20+,21-,22-,25-,26-/m0/s1

> <INCHI_KEY>
BGEODRYTLBLROB-GNRBGUANSA-N

> <FORMULA>
C26H36O12

> <MOLECULAR_WEIGHT>
540.562

> <EXACT_MASS>
540.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.15178255088945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.8697602150000003

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198430885984482

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206983477611264

> <JCHEM_PKA_STRONGEST_BASIC>
-2.217047406800316

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
131.9954

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

> <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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.669  -0.000   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  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   18                                                            
CONECT   24   17   25                                                       
CONECT   25   24                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   33                                                            
CONECT   38   29                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3R,4AS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4ah,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₂

Average Mass

540.5620 Da

Monoisotopic Mass

540.22068 Da

IUPAC Name

(3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

Traditional Name

(3R,4aS,5S,6S)-5-ethenyl-1-oxo-6-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

CAS Registry Number

Not Available

SMILES

C\C(CC\C=C(/C)C(=O)O[C@H]1C[C@H]2[C@H](C=C)[C@H](O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)OC=C2C(=O)O1)=C/CO

InChI Identifier

InChI=1S/C26H36O12/c1-4-15-16-10-19(36-23(32)14(3)7-5-6-13(2)8-9-27)37-24(33)17(16)12-34-25(15)38-26-22(31)21(30)20(29)18(11-28)35-26/h4,7-8,12,15-16,18-22,25-31H,1,5-6,9-11H2,2-3H3/b13-8+,14-7+/t15-,16-,18-,19+,20+,21-,22-,25-,26-/m0/s1

InChI Key

BGEODRYTLBLROB-GNRBGUANSA-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
Menyanthes trifoliata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Fatty alcohol
Acylal
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.13	ALOGPS
logP	0.87	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	132 m³·mol⁻¹	ChemAxon
Polarizability	54.15 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

162999938

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Foliamenthin (NP0057644)

MOL for NP0057644 (Foliamenthin)

3D MOL for NP0057644 (Foliamenthin)

3D SDF for NP0057644 (Foliamenthin)

3D-SDF for NP0057644 (Foliamenthin)

PDB for NP0057644 (Foliamenthin)

3D PDB for NP0057644 (Foliamenthin)

SMILES for NP0057644 (Foliamenthin)

INCHI for NP0057644 (Foliamenthin)

Structure for NP0057644 (Foliamenthin)

3D Structure for NP0057644 (Foliamenthin)