NP-MRD: Showing NP-Card for 3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0322097)

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Record Information

Version

2.0

Created at

2022-09-12 00:40:39 UTC

Updated at

2022-09-12 00:40:39 UTC

NP-MRD ID

NP0322097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3-Hydroxy-2-methylidene-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Ilex pubescens. Based on a literature review very few articles have been published on 3-hydroxy-2-methylidene-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202402D          

 31 32  0  0  1  0            999 V2000
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    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
    3.5724   -5.3625    0.0000 O   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  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
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 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
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    0.0540    0.6420   -1.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478    1.6940   -1.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261    2.3862   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751    1.8633   -0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6609    1.8367   -0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551    2.3337   -2.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    1.2464   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162    0.7074    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3661    0.1093    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088    0.0273    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6846   -0.5647    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7364   -1.0963    2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8835   -1.6856    2.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5943   -1.0175    2.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6404   -1.5558    4.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413   -0.4365    2.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896    2.2142   -1.7678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6206    3.5210   -2.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    1.3536   -2.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6997    0.0624   -2.4202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153   -0.0767   -1.3241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8537   -0.7528   -0.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6627   -0.6701    0.8498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9960   -1.1948    2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9173   -1.0532    3.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -1.4260    0.6194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0329   -0.5667    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943   -2.0317   -0.7645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7714   -2.8611   -0.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7280   -0.8902   -1.7538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8735   -0.1235   -1.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593    0.1179   -2.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0209    0.2071   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    2.3242    0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361    3.4726   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888    1.2368   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.7215    1.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5113    0.4313   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5634   -0.6172    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073   -1.7273    2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4592   -1.9832    4.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666   -0.3917    3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065    2.2865   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    4.0220   -2.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844    1.3116   -3.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3841    1.8643   -3.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    0.8757   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8361    0.4165    1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1242   -0.5650    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417   -2.2642    2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202   -0.2718    2.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0341   -2.2312    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8676   -1.0205    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7998   -2.6002   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5700   -3.2994    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5559   -1.3578   -2.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3886   -0.3555   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 21 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 23  1  0
 16  9  1  0
 25 51  1  0
 24 49  1  0
 24 50  1  0
 23 48  1  1
 21 47  1  1
 19 45  1  0
 19 46  1  0
 17 43  1  1
 18 44  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 13 40  1  0
 15 41  1  0
 16 42  1  0
 30 56  1  6
 31 57  1  0
 28 54  1  6
 29 55  1  0
 26 52  1  1
 27 53  1  0
M  END


  Mrv1652309122202402D          

 31 32  0  0  1  0            999 V2000
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    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
    3.5724   -5.3625    0.0000 O   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  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
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 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
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0322097

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O11/c1-10(8-29-16(25)5-3-11-2-4-12(22)13(23)6-11)14(24)9-30-20-19(28)18(27)17(26)15(7-21)31-20/h2-6,14-15,17-24,26-28H,1,7-9H2/b5-3+/t14?,15-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
WTKXHULOWFHFAA-GAJPCSOTSA-N

> <FORMULA>
C20H26O11

> <MOLECULAR_WEIGHT>
442.417

> <EXACT_MASS>
442.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.02504301130432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.7991476433333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.057848919769585

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208173992200578

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834237150017

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
105.38600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-2-methylidene-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₆O₁₁

Average Mass

442.4170 Da

Monoisotopic Mass

442.14751 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H26O11/c1-10(8-29-16(25)5-3-11-2-4-12(22)13(23)6-11)14(24)9-30-20-19(28)18(27)17(26)15(7-21)31-20/h2-6,14-15,17-24,26-28H,1,7-9H2/b5-3+/t14?,15-,17-,18+,19-,20-/m1/s1

InChI Key

WTKXHULOWFHFAA-GAJPCSOTSA-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
Ilex pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	-0.8	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	105.39 m³·mol⁻¹	ChemAxon
Polarizability	44.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

9411118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11236073

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0322097)

MOL for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0322097 (3-hydroxy-2-methylidene-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)