NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate (NP0231145)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 11:52:00 UTC

Updated at

2022-09-06 11:52:00 UTC

NP-MRD ID

NP0231145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate

Description

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. [(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate is found in Penstemon procerus. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213522D          

 35 36  0  0  1  0            999 V2000
    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
    4.6358    1.5270    2.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5857    0.8548    2.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9560    0.0379    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029   -0.2354    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099    0.1920   -0.5528 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1885    1.5197   -0.7468 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9831   -0.0101   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1786    0.6356   -0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2138   -0.8066   -2.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6092   -1.0401   -2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9665   -2.3752   -2.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662    1.0869    2.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970    1.8590    3.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101    0.4387    1.6684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    0.6251    1.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9949   -0.2045    0.9114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3241    0.0138    1.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673   -0.6022    0.2413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4741   -0.4839    0.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605   -1.7034    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4818   -1.4121    1.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2055   -0.6739    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9111   -1.3487   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5998   -0.6766   -1.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5379    0.7043   -1.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2010    1.4321   -2.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8217    1.4051   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7972    2.7812   -0.6553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1526    0.6937    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    0.1354   -1.0668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8892   -0.2286   -2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -0.1503   -1.5322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2818    0.5997   -2.6698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.1549   -0.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5887   -0.5979   -0.7618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1746    2.1787    3.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    2.1875    2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.8151    3.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -0.4578    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -1.3333    0.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0669    0.2445    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214   -0.4242   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424    1.7863   -1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9280    1.1282    0.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6544    1.3408   -1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8936   -0.1784   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3576   -1.2844   -2.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5516   -0.7814   -3.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3257   -0.3479   -2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6076   -2.5562   -3.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    1.7050    1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4689    0.4628    2.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -1.2881    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8280   -1.6525    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0936   -2.3206    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691   -2.2434    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549   -0.7900    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0025   -2.3635    1.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9513   -2.4293   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1395   -1.2440   -2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7230    0.9586   -3.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2912    3.2986    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5939    1.2507    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238    1.2295   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -0.0206   -2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162   -1.2210   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    0.3544   -2.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    1.2154   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -1.3672   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 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
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 18 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 16  1  0
 29 22  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
  5 42  1  6
  6 43  1  0
  4 40  1  0
  4 41  1  0
  3 39  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  1
 18 54  1  6
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 26 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  1
 31 65  1  0
 32 66  1  6
 33 67  1  0
 34 68  1  1
 35 69  1  0
M  END


  Mrv1652309062213522D          

 35 36  0  0  1  0            999 V2000
    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0231145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/CO)[C@H](O)C\C=C(/C)C(=O)OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O11/c1-13(7-9-25)16(26)5-3-14(2)23(32)34-12-19-20(29)21(30)22(31)24(35-19)33-10-8-15-4-6-17(27)18(28)11-15/h3-4,6-7,11,16,19-22,24-31H,5,8-10,12H2,1-2H3/b13-7+,14-3+/t16-,19-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
BRNNTXYZAIPAFB-IVFQWYFZSA-N

> <FORMULA>
C24H34O11

> <MOLECULAR_WEIGHT>
498.525

> <EXACT_MASS>
498.210111915

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.86681075344976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate

> <JCHEM_LOGP>
0.4776602506666676

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.127758558027978

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.446350120241846

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5275857370355377

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
124.92660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate

> <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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30   18   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   16   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoic acid	Generator

Chemical Formula

C₂₄H₃₄O₁₁

Average Mass

498.5250 Da

Monoisotopic Mass

498.21011 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate

Traditional Name

[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2E,5R,6E)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate

CAS Registry Number

Not Available

SMILES

C\C(=C/CO)[C@H](O)C\C=C(/C)C(=O)OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C24H34O11/c1-13(7-9-25)16(26)5-3-14(2)23(32)34-12-19-20(29)21(30)22(31)24(35-19)33-10-8-15-4-6-17(27)18(28)11-15/h3-4,6-7,11,16,19-22,24-31H,5,8-10,12H2,1-2H3/b13-7+,14-3+/t16-,19-,20-,21+,22-,24-/m1/s1

InChI Key

BRNNTXYZAIPAFB-IVFQWYFZSA-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
Penstemon procerus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Tyrosol derivative
Fatty alcohol
Catechol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Primary alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.48	ChemAxon
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	124.93 m³·mol⁻¹	ChemAxon
Polarizability	51.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163190032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate (NP0231145)

MOL for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

3D MOL for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

3D SDF for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

3D-SDF for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

PDB for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

3D PDB for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

SMILES for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

INCHI for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

Structure for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)

3D Structure for NP0231145 ([(2r,3s,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (2e,5r,6e)-5,8-dihydroxy-2,6-dimethylocta-2,6-dienoate)