NP-MRD: Showing NP-Card for (2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid (NP0244484)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:17:43 UTC

Updated at

2022-09-07 05:17:43 UTC

NP-MRD ID

NP0244484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Description

(2R,3R)-2-[4-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-hydroxyphenoxy]-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid, also known as salvianolic acid K, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid is found in Salvia deserta and Salvia officinalis. Based on a literature review very few articles have been published on (2R,3R)-2-[4-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-hydroxyphenoxy]-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207172D          

 40 42  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   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
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    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
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  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
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5 26  1  0  0  0  0
  2 27  1  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  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
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    3.9606   -2.0877   -3.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084   -1.4621   -2.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086   -1.0549   -2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -0.3985   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.0397   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -0.1758   -1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8547    0.2712   -1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665    0.9587   -0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480    1.3469   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    1.9895    0.9527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4438    3.3838    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848    3.7174   -0.6769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0742    4.2575    1.3605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3202    1.2661    1.4196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9969   -0.0178    1.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3397    1.2162    0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4336    2.0893    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3893    2.0591   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3175    1.1938   -1.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2698    1.1520   -2.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2348    0.3319   -1.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1461   -0.5595   -2.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2821    0.3578   -0.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    1.1556    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3162    1.8171    1.7763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645    0.7050    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6117   -1.1846   -1.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9519   -1.5919   -1.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3005   -2.5835   -0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1895   -2.0246    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3085   -1.4134    1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288   -0.8530    2.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2058   -0.8797    3.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2439   -0.3159    4.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931   -1.4982    2.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.5101    3.6470 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0638   -2.0587    1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8886   -0.4847   -1.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4965    0.6962   -1.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2297   -0.7064   -1.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4905   -1.3031   -2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -0.1735   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994   -0.6954   -2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6944    0.1061   -2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362    2.1320    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8373    4.3223    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7494    1.7896    2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7473   -0.6267    1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5445    2.7937    1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2445    2.7281   -0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0734    1.7466   -2.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3880   -1.2041   -2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4385   -0.3399   -0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5453    1.9667    2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552    0.8947    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -2.1350   -2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3411   -2.9396   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484   -3.4769   -0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2460   -1.3524    0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2215   -0.3718    2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4930   -0.2870    5.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263   -1.9509    3.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1786   -2.5277    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8300   -0.2117   -2.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 28 38  1  0
 38 40  1  0
 38 39  2  0
  5 26  1  0
 26 24  2  0
 24 25  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 24  8  1  0
 23 16  1  0
 37 30  1  0
 15 48  1  0
 14 47  1  1
 10 45  1  1
  7 44  1  0
  6 43  1  0
  4 42  1  0
  3 41  1  0
 28 56  1  6
 29 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
 34 61  1  0
 36 62  1  0
 37 63  1  0
 40 64  1  0
 26 55  1  0
 25 54  1  0
 13 46  1  0
 17 49  1  0
 18 50  1  0
 20 51  1  0
 22 52  1  0
 23 53  1  0
M  END


  Mrv1652309072207172D          

 40 42  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   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
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    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
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  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
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5 26  1  0  0  0  0
  2 27  1  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  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
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]([C@@H](OC1=CC=C(\C=C\C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1O)C(O)=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O13/c28-16-5-1-14(10-18(16)30)11-22(26(35)36)39-23(33)8-3-13-2-7-21(20(32)9-13)40-25(27(37)38)24(34)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-32,34H,11H2,(H,35,36)(H,37,38)/b8-3+/t22-,24-,25-/m1/s1

> <INCHI_KEY>
AZOCLKLJIKZOLF-ZPOOTWMUSA-N

> <FORMULA>
C27H24O13

> <MOLECULAR_WEIGHT>
556.476

> <EXACT_MASS>
556.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.33803918361126

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

> <JCHEM_LOGP>
3.326967465

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.420655185049755

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8146779962999933

> <JCHEM_PKA_STRONGEST_BASIC>
-5.122743838010803

> <JCHEM_POLAR_SURFACE_AREA>
231.50999999999996

> <JCHEM_REFRACTIVITY>
135.7992

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337 -10.780   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003 -17.710   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669 -15.400   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24    8   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    5                                                       
CONECT   27    2   28                                                       
CONECT   28   27   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
CONECT   38   28   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-2-[4-[(e)-3-[(1R)-1-Carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-hydroxyphenoxy]-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate	Generator
Salvianolic acid K	MeSH

Chemical Formula

C₂₇H₂₄O₁₃

Average Mass

556.4760 Da

Monoisotopic Mass

556.12169 Da

IUPAC Name

(2R,3R)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Traditional Name

(2R,3R)-2-{4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]([C@@H](OC1=CC=C(\C=C\C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(O)=O)C=C1O)C(O)=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H24O13/c28-16-5-1-14(10-18(16)30)11-22(26(35)36)39-23(33)8-3-13-2-7-21(20(32)9-13)40-25(27(37)38)24(34)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-32,34H,11H2,(H,35,36)(H,37,38)/b8-3+/t22-,24-,25-/m1/s1

InChI Key

AZOCLKLJIKZOLF-ZPOOTWMUSA-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
Salvia deserta	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Phenoxyacetate
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Catechol
Phenoxy compound
Phenol ether
Styrene
Sugar acid
Phenol
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Ether
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic alcohol
Organic oxide
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.33	ChemAxon
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	135.8 m³·mol⁻¹	ChemAxon
Polarizability	53.34 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

8658236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10482829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid (NP0244484)

MOL for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

3D MOL for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

3D SDF for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

3D-SDF for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

PDB for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

3D PDB for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

SMILES for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

INCHI for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

Structure for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)

3D Structure for NP0244484 ((2r,3r)-2-{4-[(1e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-hydroxyphenoxy}-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid)