NP-MRD: Showing NP-Card for [(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0220956)

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Record Information

Version

2.0

Created at

2022-09-05 22:24:30 UTC

Updated at

2022-09-05 22:24:30 UTC

NP-MRD ID

NP0220956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Helonioside B belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. [(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Heloniopsis orientalis, Persicaria perfoliata, Smilax bracteata and Smilax china. [(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate was first documented in 2008 (PMID: 18329678). Based on a literature review very few articles have been published on Helonioside B (PMID: 19898799).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200242D          

 52 55  0  0  1  0            999 V2000
   -1.7244  -10.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -9.9128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -9.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -7.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378   -6.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -5.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3819   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1624   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0735   -3.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3284   -4.0556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354   -4.2271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3903   -5.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973   -5.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -5.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592   -6.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9002   -6.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6874   -3.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4944   -3.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -2.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9845   -2.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6255   -2.6578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3706   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -4.1974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7376   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -5.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -4.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -3.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1023   -4.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8869   -3.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9307   -4.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5438   -5.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723   -6.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -5.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1830   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6052   -7.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -8.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546   -9.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190  -10.0853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  1  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 46  2  0  0  0  0
 38 46  1  0  0  0  0
 32 47  1  0  0  0  0
 12 47  1  0  0  0  0
 47 48  1  6  0  0  0
  5 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END


  Mrv1652309062200242D          

 52 55  0  0  1  0            999 V2000
   -1.7244  -10.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -9.9128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5751   -9.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -7.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378   -6.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -5.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3819   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1624   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0735   -3.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3284   -4.0556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354   -4.2271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3903   -5.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973   -5.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522   -5.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592   -6.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9002   -6.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6874   -3.6140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4944   -3.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -2.8294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9845   -2.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6255   -2.6578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3706   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -4.1974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7376   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -5.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -4.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -4.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -3.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -3.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1023   -4.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8869   -3.7719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9307   -4.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5438   -5.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723   -6.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -5.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1830   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6052   -7.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -8.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546   -9.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190  -10.0853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  1  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 46  2  0  0  0  0
 38 46  1  0  0  0  0
 32 47  1  0  0  0  0
 12 47  1  0  0  0  0
 47 48  1  6  0  0  0
  5 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](CO)(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](OC(=O)\C=C\C3=CC=C(O)C(OC)=C3)[C@@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H40O18/c1-17(36)47-14-24-28(41)30(43)31(44)33(49-24)52-34(16-35)32(50-27(40)11-7-19-5-9-21(38)23(13-19)46-3)29(42)25(51-34)15-48-26(39)10-6-18-4-8-20(37)22(12-18)45-2/h4-13,24-25,28-33,35,37-38,41-44H,14-16H2,1-3H3/b10-6+,11-7+/t24-,25-,28-,29-,30+,31-,32+,33-,34+/m1/s1

> <INCHI_KEY>
JYCVXPNFPCYFKL-LCYVLNELSA-N

> <FORMULA>
C34H40O18

> <MOLECULAR_WEIGHT>
736.676

> <EXACT_MASS>
736.221464448

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
72.51822578967122

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.0575987080000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.165118101722266

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.565494557644538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.456557846878918

> <JCHEM_POLAR_SURFACE_AREA>
266.65999999999997

> <JCHEM_REFRACTIVITY>
173.94920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.219 -19.911   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.845 -18.504   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.940 -17.258   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.566 -15.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.661 -14.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.288 -13.198   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.819 -13.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.446 -11.631   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.977 -11.470   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.540 -10.385   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.009 -10.546   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.580  -7.835   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.303  -5.786   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.779  -4.321   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.364  -5.786   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.870  -6.106   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.346  -7.570   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.853  -7.891   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.329  -9.355   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.835  -9.675   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.311 -11.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.817 -11.460   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.280 -12.284   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.883  -6.746   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.390  -7.066   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.407  -5.281   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.438  -4.137   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.901  -4.961   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.425  -3.497   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.377  -7.359   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.521  -8.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.201  -9.896   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.986  -7.914   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.130  -8.944   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.595  -8.468   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.915  -6.962   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.380  -6.486   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.524  -7.517   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.989  -7.041   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       9.204  -9.023   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      10.348 -10.053   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      10.028 -11.560   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.739  -9.499   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.564  -9.300   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       0.342 -10.546   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -1.130 -14.766   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -0.503 -16.173   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -1.409 -17.419   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.782 -18.826   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   51                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   49                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   47                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17   32                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   18   31                                                  
CONECT   31   30                                                            
CONECT   32   14   33   47                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   46                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   43   38                                                       
CONECT   47   32   12   48                                                  
CONECT   48   47                                                            
CONECT   49    5   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50    3   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₀O₁₈

Average Mass

736.6760 Da

Monoisotopic Mass

736.22146 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](CO)(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](OC(=O)\C=C\C3=CC=C(O)C(OC)=C3)[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C34H40O18/c1-17(36)47-14-24-28(41)30(43)31(44)33(49-24)52-34(16-35)32(50-27(40)11-7-19-5-9-21(38)23(13-19)46-3)29(42)25(51-34)15-48-26(39)10-6-18-4-8-20(37)22(12-18)45-2/h4-13,24-25,28-33,35,37-38,41-44H,14-16H2,1-3H3/b10-6+,11-7+/t24-,25-,28-,29-,30+,31-,32+,33-,34+/m1/s1

InChI Key

JYCVXPNFPCYFKL-LCYVLNELSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helonias orientalis	LOTUS Database	35616633
Persicaria perfoliata	LOTUS Database	35616633
Smilax bracteata	LOTUS Database	35616633
Smilax china	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Ketal
Fatty acid ester
Phenol
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Ether
Acetal
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
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	1.06	ChemAxon
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	266.66 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	173.95 m³·mol⁻¹	ChemAxon
Polarizability	72.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033907

Chemspider ID

10270468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang L, Liao CC, Huang HC, Shen YC, Yang LM, Kuo YH: Antioxidant phenylpropanoid glycosides from Smilax bracteata. Phytochemistry. 2008 Apr;69(6):1398-404. doi: 10.1016/j.phytochem.2008.01.002. Epub 2008 Mar 10. [PubMed:18329678 ]
Nhiem NX, Van Kiem P, Minh CV, Ban NK, Cuong NX, Tai BH, Kim YH: Phenylpropanoid glycosides from Heterosmilax erythrantha and their antioxidant activity. Arch Pharm Res. 2009 Oct;32(10):1373-7. doi: 10.1007/s12272-009-2005-4. Epub 2009 Nov 8. [PubMed:19898799 ]
LOTUS database [Link]

Showing NP-Card for [(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0220956)

MOL for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0220956 ([(2r,3r,4s,5s)-5-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-(hydroxymethyl)oxolan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)