NP-MRD: Showing NP-Card for Lemnaloside C (NP0076775)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 21:58:02 UTC

Updated at

2022-04-28 21:58:02 UTC

NP-MRD ID

NP0076775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lemnaloside C

Description

[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Lemnaloside C is found in Lemnalia sp. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223582D          

 37 39  0  0  1  0            999 V2000
   -2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414   -2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661   -2.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952   -2.9679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237   -3.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1233   -2.9180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8517   -3.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8805   -4.1299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1809   -4.5670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4525   -4.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2097   -5.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -5.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -6.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -6.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673   -7.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   -4.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5514   -2.8682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945   -2.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  1  0  0  0  0
  7 16  1  6  0  0  0
  5 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  6  0  0  0
 18 21  1  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  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
 27 35  1  6  0  0  0
 26 36  1  6  0  0  0
 25 37  1  1  0  0  0
M  END

     RDKit          3D

 83 85  0  0  0  0  0  0  0  0999 V2000
    6.9181    0.2441    3.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5534    1.0171    2.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5609    1.9303    1.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483    0.9500    1.9195 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1031    0.5378    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123    0.4319    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616    0.0244   -1.3519 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1208   -1.2971   -1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    0.0880   -1.8702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4649    1.4346   -1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702    1.4558   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6770    0.4315   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2323    0.7229   -2.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.7263    0.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    0.1579    0.5739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7462    1.0969    0.5386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9246    0.3997    0.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0341    1.1375    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3872    2.3560    0.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8672    2.5569   -0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2173    3.9324   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0049    1.5461   -1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8589   -0.9769    1.1596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1007   -1.3014    1.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120   -1.1736    2.2239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4006   -1.0264    3.4831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6397   -0.2479    2.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4409   -0.7665    2.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0197   -0.8950   -0.6685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9731   -2.0248   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895   -3.2818   -1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491   -2.9241   -2.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772   -3.7652   -3.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498   -1.8130   -2.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -1.0723   -1.5087 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4996    2.1794    2.0699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4233    2.0818    2.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9174    0.2762    3.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2010   -0.4161    3.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3252    2.1626    2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0996    1.3584    1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1440    2.8708    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.2122    2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6083   -0.4329    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5877    1.3580   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    1.5048    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1705   -0.2554    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0855    0.7721   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -1.9809   -2.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -1.8139   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1780   -1.2361   -1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954    0.0497   -2.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334    2.2102   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592    1.8689   -2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9366    1.1316    0.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621    2.4658   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2045    0.2603   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    0.2656   -2.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    1.8099   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -0.6733    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2496    0.2691   -0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9003    0.4129    1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7242    1.2557    2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2047    3.8747   -2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5882    4.7083   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2747    4.1075   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329   -1.7576    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2518   -2.2922    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347   -2.2129    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215   -0.9253    4.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    0.6510    2.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5069   -1.5880    2.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3797   -0.9402    0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -1.8767   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.3257    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877   -3.3338   -0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475   -4.1685   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604   -4.7642   -3.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490   -3.9528   -4.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661   -3.3315   -4.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1458   -1.4641   -3.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -1.7946   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5001    2.8071    3.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 36  1  0
 36 37  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 17 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 12 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 35  9  1  0
 27 15  1  0
 35 29  1  0
  8 49  1  0
  8 50  1  0
  8 51  1  0
  7 48  1  6
  6 46  1  0
  6 47  1  0
  5 44  1  0
  5 45  1  0
  4 43  1  1
 37 83  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  1 38  1  0
  1 39  1  0
  9 52  1  6
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 13 57  1  0
 13 58  1  0
 13 59  1  0
 15 60  1  6
 17 61  1  6
 18 62  1  0
 18 63  1  0
 21 64  1  0
 21 65  1  0
 21 66  1  0
 23 67  1  6
 24 68  1  0
 25 69  1  1
 26 70  1  0
 27 71  1  1
 28 72  1  0
 29 73  1  1
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 33 78  1  0
 33 79  1  0
 33 80  1  0
 34 81  1  0
 35 82  1  1
M  END


  Mrv1652304282223582D          

 37 39  0  0  1  0            999 V2000
   -2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414   -2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8414   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661   -2.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952   -2.9679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237   -3.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1233   -2.9180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8517   -3.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8805   -4.1299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1809   -4.5670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4525   -4.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2097   -5.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9381   -5.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -6.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -6.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673   -7.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   -4.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5514   -2.8682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945   -2.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  1  0  0  0
 14 15  1  0  0  0  0
  7 16  1  6  0  0  0
  5 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  6  0  0  0
 18 21  1  0  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  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
 27 35  1  6  0  0  0
 26 36  1  6  0  0  0
 25 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@H](OO)C(C)=C)[C@@H]1CC[C@](C)(O[C@@H]2O[C@H](COC(C)=O)[C@H](O)[C@H](O)[C@H]2O)[C@H]2CCC(C)=C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O9/c1-15(2)22(37-33)10-8-17(4)19-11-12-28(6,21-9-7-16(3)13-20(19)21)36-27-26(32)25(31)24(30)23(35-27)14-34-18(5)29/h13,17,19-27,30-33H,1,7-12,14H2,2-6H3/t17-,19+,20+,21+,22+,23-,24+,25+,26-,27+,28+/m1/s1

> <INCHI_KEY>
HEORXRPTBCZNRT-UAGBQVOPSA-N

> <FORMULA>
C28H46O9

> <MOLECULAR_WEIGHT>
526.667

> <EXACT_MASS>
526.314183061

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.482740911615856

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.145181974333331

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.317580233962488

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.592128866968014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649085238445606

> <JCHEM_POLAR_SURFACE_AREA>
134.91

> <JCHEM_REFRACTIVITY>
136.5911

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.747  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.977  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.437  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.183   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.493   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.183   4.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.953  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.183  -1.334   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.437   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.127  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.357  -4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.127  -5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -5.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.183  -4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.283  -4.817   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.031  -5.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.391  -6.263   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.697  -5.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.057  -6.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.110  -7.709   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.804  -8.525   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.445  -7.802   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.858 -10.064   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.218 -10.787   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.272 -12.326   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.631 -13.049   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.966 -13.142   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.470  -8.432   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -10.363  -5.354   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -7.643  -3.908   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22   23                                             
CONECT    4    3    5   20                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    5   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19    4                                                       
CONECT   21   18                                                            
CONECT   22    3                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   27   36                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27                                                            
CONECT   36   26                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4ar,8as)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₈H₄₆O₉

Average Mass

526.6670 Da

Monoisotopic Mass

526.31418 Da

IUPAC Name

[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4S,5R,6S)-6-{[(1S,4S,4aR,8aS)-4-[(2R,5S)-5-hydroperoxy-6-methylhept-6-en-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@H](OO)C(C)=C)[C@@H]1CC[C@](C)(O[C@@H]2O[C@H](COC(C)=O)[C@H](O)[C@H](O)[C@H]2O)[C@H]2CCC(C)=C[C@@H]12

InChI Identifier

InChI=1S/C28H46O9/c1-15(2)22(37-33)10-8-17(4)19-11-12-28(6,21-9-7-16(3)13-20(19)21)36-27-26(32)25(31)24(30)23(35-27)14-34-18(5)29/h13,17,19-27,30-33H,1,7-12,14H2,2-6H3/t17-,19+,20+,21+,22+,23-,24+,25+,26-,27+,28+/m1/s1

InChI Key

HEORXRPTBCZNRT-UAGBQVOPSA-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
Lemnalia sp.	-	KNApSAcK

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
Biflorane diterpenoid
Diterpenoid
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Hydroperoxide
Carboxylic acid ester
Alkyl hydroperoxide
Oxacycle
Organoheterocyclic compound
Polyol
Peroxol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.6	ALOGPS
logP	3.15	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.59 m³·mol⁻¹	ChemAxon
Polarizability	57.48 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

162919363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lemnaloside C (NP0076775)

MOL for NP0076775 (Lemnaloside C)

3D MOL for NP0076775 (Lemnaloside C)

3D SDF for NP0076775 (Lemnaloside C)

3D-SDF for NP0076775 (Lemnaloside C)

PDB for NP0076775 (Lemnaloside C)

3D PDB for NP0076775 (Lemnaloside C)

SMILES for NP0076775 (Lemnaloside C)

INCHI for NP0076775 (Lemnaloside C)

Structure for NP0076775 (Lemnaloside C)

3D Structure for NP0076775 (Lemnaloside C)