NP-MRD: Showing NP-Card for (5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid (NP0149786)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 05:43:28 UTC

Updated at

2022-09-02 05:43:29 UTC

NP-MRD ID

NP0149786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid

Description

Pagoside belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid is found in Harpagophytum zeyheri. (5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid was first documented in 2003 (PMID: 14598207). Based on a literature review very few articles have been published on Pagoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207432D          

 35 37  0  0  1  0            999 V2000
    2.1434   -2.8875    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
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -3.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5023   -5.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3228   -5.3045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6583   -4.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788   -4.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8077   -5.9720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6282   -5.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3161   -7.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -6.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -6.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -7.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -9.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979   -9.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -9.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075  -10.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581   -9.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -8.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 22 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
    1.1745   -2.7605   -1.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -1.3240   -1.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -0.6795   -0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -1.2799    0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -0.6718    2.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -2.6542    1.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2617    0.7195   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277    1.4257   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557    0.9563    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9887    1.1137   -0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574    0.7069    0.7692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6289   -0.3759    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9894   -0.4644    0.2594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4249   -1.7026   -0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8237   -2.8487   -0.0160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7269    0.7050   -0.3598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0007    0.8537    0.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9262    1.9810   -0.2031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0533    2.1529   -1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    1.8084    1.0146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8666    1.4833    2.0878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2649    0.9664   -1.8064 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5392    0.8428   -1.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705    1.7243   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3915    2.7639   -2.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9037    1.5218   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463    0.4435   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4133    0.1699    0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5291    0.9692    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7201    0.6248    1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8099   -0.5402    1.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9980   -0.8944    2.4704 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7193   -1.3499    1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5465   -0.9985    1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9524   -0.3329   -2.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6369   -3.0258   -2.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736   -3.3982   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -3.0504   -0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1089   -3.3110    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    2.4632   -0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003    1.6496    1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.0683    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    0.3575    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3437   -0.6683    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038   -1.8457   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0940   -1.6261   -1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1879   -3.6088   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7680    0.5061   -1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1313    1.7193    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5948    2.8521   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0124    1.3411   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555    2.7629    1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890    1.0392    2.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655    1.8527   -2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6881    2.2429   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018   -0.2466    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4732    1.8891   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5799    1.2753    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6850   -1.4538    1.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947   -2.2739    2.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6857   -1.6584    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -0.2297   -3.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -0.5421   -3.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  3  7  1  0
  7  8  2  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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  7 22  1  0
 22 35  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 35  2  1  0
 34 28  1  0
 20 11  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  6 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 11 43  1  1
 13 44  1  1
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  6
 17 49  1  0
 18 50  1  1
 19 51  1  0
 20 52  1  1
 21 53  1  0
 22 54  1  6
 35 62  1  0
 35 63  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 30 58  1  0
 32 59  1  0
 33 60  1  0
 34 61  1  0
M  END


  Mrv1652309022207432D          

 35 37  0  0  1  0            999 V2000
    2.1434   -2.8875    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
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -3.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5023   -5.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3228   -5.3045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6583   -4.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788   -4.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8077   -5.9720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6282   -5.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3161   -7.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -6.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -6.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -7.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -9.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979   -9.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -9.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075  -10.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581   -9.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -8.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 22 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(O)=O)\C(=C/CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C1)OC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O11/c1-12-10-16(34-18(27)7-4-13-2-5-14(26)6-3-13)15(19(12)23(31)32)8-9-33-24-22(30)21(29)20(28)17(11-25)35-24/h2-8,16-17,20-22,24-26,28-30H,9-11H2,1H3,(H,31,32)/b7-4+,15-8-/t16?,17-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
CBJNLOVRAFQEQH-VUIINJGZSA-N

> <FORMULA>
C24H28O11

> <MOLECULAR_WEIGHT>
492.477

> <EXACT_MASS>
492.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.68301784769346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.31325261766666673

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.39789437674223

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8592016803270655

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083551139995

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
121.6545

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid

> <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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.712  -7.359   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.856  -8.390   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.032  -5.853   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.676 -10.546   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.208 -10.385   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.113 -11.631   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.645 -11.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.271 -10.063   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.802  -9.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.429  -8.495   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.960  -8.334   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.708 -11.148   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.239 -10.987   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.081 -12.555   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.986 -13.800   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.550 -12.716   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.923 -14.122   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.326 -10.546   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.952 -11.953   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.484 -12.114   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.047 -13.198   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.673 -14.605   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.768 -15.851   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.395 -17.258   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.489 -18.504   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.042 -18.343   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.947 -19.589   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.669 -16.936   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.237 -15.690   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    7   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
CONECT   35   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₁₁

Average Mass

492.4770 Da

Monoisotopic Mass

492.16316 Da

IUPAC Name

(5E)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid

Traditional Name

(5E)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C(C(O)=O)\C(=C/CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C1)OC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H28O11/c1-12-10-16(34-18(27)7-4-13-2-5-14(26)6-3-13)15(19(12)23(31)32)8-9-33-24-22(30)21(29)20(28)17(11-25)35-24/h2-8,16-17,20-22,24-26,28-30H,9-11H2,1H3,(H,31,32)/b7-4+,15-8-/t16?,17-,20-,21+,22-,24-/m1/s1

InChI Key

CBJNLOVRAFQEQH-VUIINJGZSA-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
Harpagophytum zeyheri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Primary alcohol
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	0.55	ALOGPS
logP	0.31	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	121.65 m³·mol⁻¹	ChemAxon
Polarizability	47.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

C00003083

Chemspider ID

29814281

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45783209

PDB ID

Not Available

ChEBI ID

182054

Good Scents ID

Not Available

References

General References

Boje K, Lechtenberg M, Nahrstedt A: New and known iridoid- and phenylethanoid glycosides from Harpagophytum procumbens and their in vitro inhibition of human leukocyte elastase. Planta Med. 2003 Sep;69(9):820-5. doi: 10.1055/s-2003-43225. [PubMed:14598207 ]
LOTUS database [Link]

Showing NP-Card for (5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid (NP0149786)

MOL for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

3D MOL for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

3D SDF for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

3D-SDF for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

PDB for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

3D PDB for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

SMILES for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

INCHI for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

Structure for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)

3D Structure for NP0149786 ((5e)-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-methyl-5-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)cyclopent-1-ene-1-carboxylic acid)