NP-MRD: Showing NP-Card for [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0150961)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 07:12:09 UTC

Updated at

2022-09-02 07:12:10 UTC

NP-MRD ID

NP0150961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Baccharis dracunculifolia. Based on a literature review very few articles have been published on [(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209122D          

 38 40  0  0  1  0            999 V2000
   -3.3318   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173  -10.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1884  -11.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -9.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9550   -9.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3840   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985  -10.2257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129   -9.8132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8992   -8.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7061   -8.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186   -9.5357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7861   -9.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6707  -10.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4157  -10.9334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678  -11.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128  -12.3311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7747  -11.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0297  -10.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8366  -10.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0916   -9.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8985   -9.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4506  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2576   -9.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1956  -10.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477  -11.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3887  -11.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666  -10.1488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7381  -10.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695  -11.0507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3840  -11.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550  -11.4632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9550  -12.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406  -11.0507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4739  -11.4632    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  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
 15 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
   -8.3961    1.5654   -1.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9087    0.1857   -1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1253   -0.5567   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7087   -0.6618   -0.5264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7018   -1.4275   -1.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8540   -1.3044    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409   -0.6202    0.7089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6280   -1.3188    0.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4411   -0.6784    0.5413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3353   -1.4014   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0844   -0.9100    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430    0.4011   -0.3231 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2080    0.3769   -1.2238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925    1.4882   -0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850    1.3597    0.6049 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5579    2.5178    1.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7918    0.0994    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1236    0.1084    0.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223    0.9310    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8699    1.8096    1.8678 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4992    0.8359    0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8420   -0.0585   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1769   -0.2175   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3815   -1.2010   -1.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6289   -1.3811   -2.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7135   -0.6081   -2.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9613   -0.8323   -2.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4877    0.3700   -1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5257    1.1851   -0.7624 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2413    0.5684   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990    1.1508    0.8995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0667    2.3537    1.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830   -0.8363    2.0354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1066    0.4593    2.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3977   -1.4796    2.6470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5107   -2.8205    2.4253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6076   -0.6789    2.2047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4646    0.5900    2.7836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6156    1.9077   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0560    1.6497   -2.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2578    2.2928   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8681   -0.4141   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0012    0.2083   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2684   -0.0028    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5973   -1.5631    0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3060    0.3479   -0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4886   -2.2283   -1.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7228   -1.9390   -1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9659   -0.7926   -2.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6541    0.3998    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4302    0.3773    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382   -2.4525    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664   -1.5479   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643    0.8325   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    2.4356   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    1.3981   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7626    3.1945    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896   -0.7301    0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595   -0.0389    2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2349    1.5096    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472   -0.7142   -0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5615   -1.8547   -2.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7958   -2.1617   -3.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7785   -0.3047   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4627    1.1459   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1100    1.3617    0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5282    0.5743    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028    2.3824    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -1.3515    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3504    1.1561    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3210   -1.3249    3.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2107   -3.1523    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -1.2116    2.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9370    1.2475    2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 15 31  1  0
 31 32  1  0
  9 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  7  1  0
 31 12  1  0
 30 23  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  6
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  6
  9 51  1  6
 10 52  1  0
 10 53  1  0
 12 54  1  6
 14 55  1  0
 14 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 22 61  1  0
 24 62  1  0
 25 63  1  0
 27 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  1
 32 68  1  0
 33 69  1  6
 34 70  1  0
 35 71  1  1
 36 72  1  0
 37 73  1  1
 38 74  1  0
M  END


  Mrv1652309022209122D          

 38 40  0  0  1  0            999 V2000
   -3.3318   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173  -10.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1884  -11.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -9.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9550   -9.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695  -10.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3840   -9.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985  -10.2257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129   -9.8132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8992   -8.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7061   -8.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186   -9.5357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7861   -9.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6707  -10.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4157  -10.9334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678  -11.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128  -12.3311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7747  -11.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0297  -10.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8366  -10.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0916   -9.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8985   -9.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4506  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2576   -9.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1956  -10.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7477  -11.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3887  -11.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666  -10.1488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7381  -10.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6695  -11.0507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3840  -11.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550  -11.4632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9550  -12.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406  -11.0507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4739  -11.4632    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  1  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
 15 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0150961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H](C)O[C@@H]1O[C@H](CO[C@@H]2OC[C@](O)(COC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O13/c1-3-4-13(2)37-23-21(31)20(30)19(29)17(38-23)10-34-24-22(32)25(33,12-36-24)11-35-18(28)8-6-14-5-7-15(26)16(27)9-14/h5-9,13,17,19-24,26-27,29-33H,3-4,10-12H2,1-2H3/b8-6+/t13-,17+,19+,20-,21+,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
JEOODUYTNFLEHG-WSDPVARKSA-N

> <FORMULA>
C25H36O13

> <MOLECULAR_WEIGHT>
544.55

> <EXACT_MASS>
544.215591219

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.594396912748905

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.6013223396666667

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.64521730918317

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207214664427987

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486681785612722

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
129.16670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.219 -18.318   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.886 -19.088   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.552 -18.318   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.218 -19.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.218 -20.628   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.885 -18.318   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.449 -19.088   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.783 -18.318   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.116 -19.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.450 -18.318   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.784 -19.088   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.117 -18.318   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.278 -16.786   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.785 -16.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.555 -17.800   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.801 -16.895   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.585 -18.944   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.109 -20.409   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.140 -21.553   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.664 -23.018   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.646 -21.233   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.122 -19.769   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.628 -19.449   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.104 -17.984   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.611 -17.664   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.641 -18.808   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.147 -18.488   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      17.165 -20.273   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.196 -21.417   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.659 -20.593   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.524 -18.944   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.844 -20.451   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.116 -20.628   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.450 -21.398   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.783 -21.398   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.783 -22.938   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.449 -20.628   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.885 -21.398   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   31                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31   15   12   32                                                  
CONECT   32   31                                                            
CONECT   33    9   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    7   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(3S,4R,5R)-3,4-Dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₆O₁₃

Average Mass

544.5500 Da

Monoisotopic Mass

544.21559 Da

IUPAC Name

[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CCC[C@H](C)O[C@@H]1O[C@H](CO[C@@H]2OC[C@](O)(COC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H36O13/c1-3-4-13(2)37-23-21(31)20(30)19(29)17(38-23)10-34-24-22(32)25(33,12-36-24)11-35-18(28)8-6-14-5-7-15(26)16(27)9-14/h5-9,13,17,19-24,26-27,29-33H,3-4,10-12H2,1-2H3/b8-6+/t13-,17+,19+,20-,21+,22-,23+,24+,25+/m0/s1

InChI Key

JEOODUYTNFLEHG-WSDPVARKSA-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
Baccharis dracunculifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Hydroxycinnamic acid or derivatives
Alkyl glycoside
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Styrene
Catechol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Oxolane
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
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	0.36	ALOGPS
logP	0.6	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	129.17 m³·mol⁻¹	ChemAxon
Polarizability	55.59 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

9257273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11082126

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0150961)

MOL for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0150961 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2s)-pentan-2-yloxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)