NP-MRD: Showing NP-Card for [(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0164682)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 23:36:49 UTC

Updated at

2022-09-02 23:36:49 UTC

NP-MRD ID

NP0164682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Hydropiperoside belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. [(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Persicaria hydropiper, Persicaria lapathifolia and Persicaria pensylvanica. Based on a literature review very few articles have been published on Hydropiperoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032201362D          

 56 60  0  0  1  0            999 V2000
    4.0107   -6.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8077   -5.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282   -5.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1131   -6.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9336   -6.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7775   -7.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 O   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
    2.5559   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5914   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6533   -2.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -2.7564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -1.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9701   -0.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4800    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7350    1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321    0.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -3.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0545   -2.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -2.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4135   -2.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2204   -2.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1164   -3.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9233   -3.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643   -4.2271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8193   -5.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7574   -4.0556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2053   -4.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6914   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -5.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7064   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195   -4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041   -4.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7172   -5.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -4.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -4.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4579   -3.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -3.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  2  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  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  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 16 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 16 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  2  0  0  0  0
 48 54  1  0  0  0  0
 42 55  1  0  0  0  0
 14 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END


  Mrv1652309032201362D          

 56 60  0  0  1  0            999 V2000
    4.0107   -6.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8077   -5.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282   -5.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1131   -6.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9336   -6.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7775   -7.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 O   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
    2.5559   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5914   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6533   -2.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2053   -2.7564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -1.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9701   -0.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4800    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7350    1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321    0.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7771   -0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -3.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0545   -2.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -2.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4135   -2.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2204   -2.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1164   -3.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9233   -3.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643   -4.2271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8193   -5.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7574   -4.0556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2053   -4.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6914   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -5.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7064   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195   -4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041   -4.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7172   -5.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5018   -4.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -4.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4579   -3.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756   -3.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  2  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  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  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 16 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 16 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  2  0  0  0  0
 48 54  1  0  0  0  0
 42 55  1  0  0  0  0
 14 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0164682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H](O[C@]2(COC(=O)\C=C\C3=CC=C(O)C=C3)O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H40O17/c40-19-28-33(47)35(49)36(50)38(53-28)56-39(21-52-31(45)17-8-23-3-12-26(42)13-4-23)37(54-32(46)18-9-24-5-14-27(43)15-6-24)34(48)29(55-39)20-51-30(44)16-7-22-1-10-25(41)11-2-22/h1-18,28-29,33-38,40-43,47-50H,19-21H2/b16-7+,17-8+,18-9+/t28-,29-,33-,34-,35+,36-,37+,38-,39+/m1/s1

> <INCHI_KEY>
VJVCHSAJVKCENR-QDCYMVOUSA-N

> <FORMULA>
C39H40O17

> <MOLECULAR_WEIGHT>
780.732

> <EXACT_MASS>
780.226549828

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
78.38523816719665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5S)-3-hydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.6621412253333343

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.398077745184358

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.921223397807902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98108491281414

> <JCHEM_POLAR_SURFACE_AREA>
268.42999999999995

> <JCHEM_REFRACTIVITY>
193.41990000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5S)-3-hydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       7.487 -13.037   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.113 -11.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.645 -11.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.550 -12.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.081 -12.555   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.708 -11.148   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.239 -10.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.144 -12.233   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.676 -12.072   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.518 -13.639   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.986 -13.800   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.208 -10.385   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.676 -10.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.247  -7.835   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.971  -5.786   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.446  -4.321   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.953  -4.001   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.983  -5.145   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.429  -2.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.935  -2.216   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.411  -0.751   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.380   0.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.856   1.858   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.363   2.178   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.839   3.643   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.393   1.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.917  -0.431   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.031  -5.786   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.538  -6.106   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.568  -4.961   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.075  -5.281   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.105  -4.137   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.611  -4.457   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.551  -6.746   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.057  -7.066   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.520  -7.891   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.996  -9.355   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.014  -7.570   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.983  -8.715   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.291  -7.359   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.146  -8.390   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.466  -9.896   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.319  -7.914   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.463  -8.944   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.928  -8.468   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -5.072  -9.499   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.537  -9.023   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -6.857  -7.517   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -8.321  -7.041   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -5.712  -6.486   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.248  -6.962   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       2.326 -10.546   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   55                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30   42                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   16   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
CONECT   42   16   43   55                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   54                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   48                                                       
CONECT   55   42   14   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₄₀O₁₇

Average Mass

780.7320 Da

Monoisotopic Mass

780.22655 Da

IUPAC Name

[(2R,3R,4S,5S)-3-hydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H](O[C@]2(COC(=O)\C=C\C3=CC=C(O)C=C3)O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C39H40O17/c40-19-28-33(47)35(49)36(50)38(53-28)56-39(21-52-31(45)17-8-23-3-12-26(42)13-4-23)37(54-32(46)18-9-24-5-14-27(43)15-6-24)34(48)29(55-39)20-51-30(44)16-7-22-1-10-25(41)11-2-22/h1-18,28-29,33-38,40-43,47-50H,19-21H2/b16-7+,17-8+,18-9+/t28-,29-,33-,34-,35+,36-,37+,38-,39+/m1/s1

InChI Key

VJVCHSAJVKCENR-QDCYMVOUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Persicaria hydropiper	LOTUS Database	35616633
Persicaria lapathifolia	LOTUS Database	35616633
Polygonum pensylvanicum	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
Cinnamic acid ester
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Ketal
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Oxolane
Enoate ester
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Primary alcohol
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.63	ALOGPS
logP	3.66	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	268.43 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	193.42 m³·mol⁻¹	ChemAxon
Polarizability	78.39 Å³	ChemAxon
Number of Rings	5	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

C00046024

Chemspider ID

8525739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10350284

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,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0164682)

MOL for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0164682 ([(2r,3r,4s,5s)-3-hydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)