NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0322043)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 00:35:25 UTC

Updated at

2022-09-12 00:35:25 UTC

NP-MRD ID

NP0322043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

FUCATOSIDE A belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Lantana fucata and Lepisorus contortus. Based on a literature review very few articles have been published on FUCATOSIDE A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202352D          

 43 46  0  0  1  0            999 V2000
    1.2653   -9.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -9.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062  -10.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267  -10.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2117   -9.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321   -9.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677  -10.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882  -10.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828  -11.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183  -11.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623  -11.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -8.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942   -8.4806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2586   -7.7269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7435   -7.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -7.6407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -6.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125   -6.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5520   -4.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -4.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -3.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -5.4349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4521   -5.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -8.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -8.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -8.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -8.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3220  -10.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070  -10.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274  -10.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1124  -11.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9630  -10.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -9.9655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781   -9.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112   -9.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -9.1480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4448   -9.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0401  -10.5691    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  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  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
 17 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 77 80  0  0  0  0  0  0  0  0999 V2000
    4.0697    1.0303    1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600    0.0571    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392   -0.4157    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5858    0.1502    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8830   -0.2809    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171    0.4102    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2713    0.0437    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4613   -1.0161   -0.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7393   -1.3768   -1.2671 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3420   -1.7074   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5076   -2.7781   -2.1029 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0680   -1.3374   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115   -0.6113    0.3951 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082   -0.2661    0.8276 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8351    0.1673   -0.3265 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3252    1.3081   -0.9517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5793    0.3587    0.1734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3184    0.8609   -0.9058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307    2.0694   -0.5879 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2977    1.8666   -0.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    3.0624   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    4.0436   -1.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6803    5.0093   -0.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    4.6522   -2.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4696    3.6176   -3.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    3.1526   -1.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4713    3.8367   -1.3561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0651   -1.0423    0.5616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0465   -0.9895    1.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549   -1.4130    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3846   -1.3956    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6033   -1.8798    1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4202   -0.9576    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5538   -1.3317   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8983   -2.6640   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0300   -3.0846   -0.8153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1151   -3.5928    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4819   -4.9332    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9698   -3.1979    1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0399   -1.9056    0.8406 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -1.3964    1.5371 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6984   -1.0135    2.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528   -2.1156    3.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4558   -1.2549   -0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4976    1.0049    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8833    1.2476    1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1749    0.5738    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8156   -2.1634   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6758   -3.2747   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2141   -1.8998   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    0.6051    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -0.6913   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    1.1648   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479    1.0426    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215    2.4030    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    2.8716   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379    3.4553   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2404    5.8021   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    5.4351   -3.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964    5.1303   -2.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1289    3.8849   -4.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    2.7142   -2.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    4.5364   -0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -1.4292   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -2.4257    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5380   -0.7304    0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168   -0.3836    2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171   -2.1104    2.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788    0.0985    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1890   -0.5986   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6476   -2.4418   -1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9311   -5.6483    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -3.9260    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807   -2.2239    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -0.6449    3.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098   -0.1732    2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4333   -2.9441    3.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
 43 42  1  0
 42 41  1  0
 41 40  1  0
 40 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 28 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  1  1
 22 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 14 41  1  0
 12  5  1  0
 39 32  1  0
 26 19  1  0
 43 77  1  0
 42 75  1  0
 42 76  1  0
 41 74  1  1
 28 64  1  6
 30 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 33 69  1  0
 34 70  1  0
 36 71  1  0
 38 72  1  0
 39 73  1  0
 17 54  1  1
 19 55  1  1
 21 56  1  0
 21 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  6
 27 63  1  0
 15 52  1  6
 16 53  1  0
 14 51  1  1
  3 44  1  0
  4 45  1  0
  6 46  1  0
  7 47  1  0
  9 48  1  0
 11 49  1  0
 12 50  1  0
M  END


  Mrv1652309122202352D          

 43 46  0  0  1  0            999 V2000
    1.2653   -9.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -9.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062  -10.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267  -10.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2117   -9.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321   -9.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677  -10.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882  -10.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828  -11.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183  -11.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623  -11.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -8.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942   -8.4806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2586   -7.7269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7435   -7.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -7.6407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -6.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125   -6.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5520   -4.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -4.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -3.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -5.4349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4521   -5.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -8.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8673   -8.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -8.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727   -8.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3220  -10.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070  -10.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274  -10.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1124  -11.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9630  -10.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -9.9655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781   -9.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112   -9.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093   -9.1480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4448   -9.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0401  -10.5691    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  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  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
 17 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O15/c29-11-20-23(42-21(35)6-3-14-1-4-16(31)18(33)9-14)22(36)24(43-27-25(37)28(38,12-30)13-40-27)26(41-20)39-8-7-15-2-5-17(32)19(34)10-15/h1-6,9-10,20,22-27,29-34,36-38H,7-8,11-13H2/b6-3+/t20-,22+,23-,24-,25+,26-,27+,28-/m1/s1

> <INCHI_KEY>
MNAIMEPYDVJSJU-WLJWCVHXSA-N

> <FORMULA>
C28H34O15

> <MOLECULAR_WEIGHT>
610.565

> <EXACT_MASS>
610.189770395

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.32862655054615

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
0.2668519793333341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.642499953293475

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.00999562284228

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423791405601103

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
144.20369999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       2.362 -18.644   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.267 -17.398   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.799 -17.559   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.425 -18.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.957 -19.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.862 -17.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.393 -18.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.020 -19.449   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.551 -19.610   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.115 -20.695   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.741 -22.102   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.583 -20.534   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.641 -15.991   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.109 -15.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.483 -14.424   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.388 -13.178   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.049 -14.263   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.675 -12.856   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.770 -11.610   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.770 -11.610   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.246 -10.145   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.030  -8.096   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.030  -8.096   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.555  -6.631   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.246 -10.145   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.711  -9.669   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.954 -15.508   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.486 -15.347   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.391 -16.593   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.922 -16.432   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.828 -17.678   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.201 -19.085   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.106 -20.331   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.638 -20.170   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.543 -21.416   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -9.264 -18.763   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -10.796 -18.602   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -8.359 -17.517   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.328 -16.915   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.204 -17.076   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.830 -18.483   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.075 -19.729   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   26                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   22   19   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   28   41                                                       
CONECT   41   40   14   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₁₅

Average Mass

610.5650 Da

Monoisotopic Mass

610.18977 Da

IUPAC Name

(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C28H34O15/c29-11-20-23(42-21(35)6-3-14-1-4-16(31)18(33)9-14)22(36)24(43-27-25(37)28(38,12-30)13-40-27)26(41-20)39-8-7-15-2-5-17(32)19(34)10-15/h1-6,9-10,20,22-27,29-34,36-38H,7-8,11-13H2/b6-3+/t20-,22+,23-,24-,25+,26-,27+,28-/m1/s1

InChI Key

MNAIMEPYDVJSJU-WLJWCVHXSA-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
Lantana fucata	LOTUS Database	35616633
Lepisorus contortus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Tyrosol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:68342 )

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	0.27	ChemAxon
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	60.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047894

Chemspider ID

24667217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44254697

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)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0322043)

MOL for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0322043 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)