NP-MRD: Showing NP-Card for (+)-Smilaside J (NP0073739)

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Record Information

Version

2.0

Created at

2022-04-28 18:57:52 UTC

Updated at

2022-04-28 18:57:52 UTC

NP-MRD ID

NP0073739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Smilaside J

Description

[(2R,3S,4S,5S)-4-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (+)-Smilaside J is found in Smilax bracteata. Based on a literature review very few articles have been published on [(2R,3S,4S,5S)-4-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220572D          

 60 64  0  0  1  0            999 V2000
   -1.6242   -5.0437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4492   -5.0437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7041   -4.2590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367   -3.7741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3693   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317   -3.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068   -3.0467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4018   -2.3280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4232   -2.3193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8432   -3.0294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4382   -3.7482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3868   -3.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -4.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681   -3.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -1.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8217   -1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -3.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667   -3.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717   -2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517   -1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4966   -2.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016   -1.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7266   -1.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1465   -2.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9715   -2.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3765   -1.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9565   -0.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316   -0.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3615   -0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1865   -0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2014   -1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888   -4.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -5.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7546   -5.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0902   -4.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395   -6.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0600   -6.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449   -6.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2094   -7.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6943   -8.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5148   -8.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8503   -7.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3654   -6.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9997   -8.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188   -5.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661   -6.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694   -7.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4715   -6.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6276   -6.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7769   -7.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -8.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -8.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534   -6.5286    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  1  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  4 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 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
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
  3 33  1  6  0  0  0
  2 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
 42 45  1  0  0  0  0
  1 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 52 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 55 60  1  0  0  0  0
M  END

     RDKit          3D

104108  0  0  0  0  0  0  0  0999 V2000
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   -2.7920   -6.0781    5.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3981   -4.9712    3.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -4.0220    1.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5457   -3.7902    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512   -2.8233   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4423   -2.5675   -0.9131 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9518    1.1767   -1.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5859    2.1908   -0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
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 60104  1  0
M  END


  Mrv1652304282220572D          

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 55 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](COC(=O)\C=C\C3=CC=C(O)C(OC)=C3)(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H44O19/c1-53-28-17-23(5-12-26(28)44)8-14-32(46)55-20-31-38(58-34(48)16-7-22-3-10-25(43)11-4-22)39(52)41(59-31,60-40-37(51)36(50)35(49)30(19-42)57-40)21-56-33(47)15-9-24-6-13-27(45)29(18-24)54-2/h3-18,30-31,35-40,42-45,49-52H,19-21H2,1-2H3/b14-8+,15-9+,16-7+/t30-,31-,35+,36+,37-,38-,39+,40-,41+/m1/s1

> <INCHI_KEY>
CLQPFAIQQXAUST-PQCGYLHPSA-N

> <FORMULA>
C41H44O19

> <MOLECULAR_WEIGHT>
840.784

> <EXACT_MASS>
840.247679197

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
84.74493959232133

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.3467986939999994

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.721464162357654

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.17266864637585

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98108491280229

> <JCHEM_POLAR_SURFACE_AREA>
286.89

> <JCHEM_REFRACTIVITY>
206.34629999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.20e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -3.032  -9.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.572  -9.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.048  -7.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.802  -7.045   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.556  -7.950   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.046  -5.703   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.506  -5.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.750  -4.346   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.790  -4.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.574  -5.655   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.818  -6.997   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.722  -7.013   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.602  -8.322   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.142  -8.306   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.114  -5.639   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.546  -2.988   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.534  -3.020   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.558  -5.703   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.098  -5.687   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.854  -4.346   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.070  -3.020   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.394  -4.329   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.150  -2.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.690  -2.972   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.473  -4.297   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -13.013  -4.281   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.769  -2.939   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.985  -1.614   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.446  -1.630   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.741  -0.272   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -15.281  -0.256   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -15.309  -2.923   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.512  -7.474   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.477 -10.661   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.009 -10.500   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.635  -9.093   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -7.914 -11.746   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.445 -11.585   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -10.351 -12.831   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.724 -14.237   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.629 -15.483   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -12.161 -15.322   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -12.787 -13.915   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.882 -12.670   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -13.066 -16.568   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -2.127 -10.661   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -0.595 -10.500   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       0.310 -11.746   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -0.316 -13.152   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       1.842 -11.585   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.747 -12.831   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.278 -12.670   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.905 -11.263   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.436 -11.102   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.342 -12.348   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       6.715 -13.754   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       5.184 -13.915   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       7.620 -15.000   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.994 -16.407   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       8.873 -12.187   0.000  0.00  0.00           O+0
CONECT    1    2    5   46                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5    6   18                                             
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    4   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33    3                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   42                                                            
CONECT   46    1   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57   58                                                  
CONECT   57   56   52                                                       
CONECT   58   56   59                                                       
CONECT   59   58                                                            
CONECT   60   55                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5S)-4-Hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₄₁H₄₄O₁₉

Average Mass

840.7840 Da

Monoisotopic Mass

840.24768 Da

IUPAC Name

[(2S,3S,4S,5R)-3-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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@@](COC(=O)\C=C\C3=CC=C(O)C(OC)=C3)(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C41H44O19/c1-53-28-17-23(5-12-26(28)44)8-14-32(46)55-20-31-38(58-34(48)16-7-22-3-10-25(43)11-4-22)39(52)41(59-31,60-40-37(51)36(50)35(49)30(19-42)57-40)21-56-33(47)15-9-24-6-13-27(45)29(18-24)54-2/h3-18,30-31,35-40,42-45,49-52H,19-21H2,1-2H3/b14-8+,15-9+,16-7+/t30-,31-,35+,36+,37-,38-,39+,40-,41+/m1/s1

InChI Key

CLQPFAIQQXAUST-PQCGYLHPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Smilax bracteata	Plant	KNApSAcK

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
Cinnamic acid ester
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
C-glycosyl compound
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	2.7	ALOGPS
logP	3.35	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	286.89 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	206.35 m³·mol⁻¹	ChemAxon
Polarizability	84.74 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162932932

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Smilaside J (NP0073739)

MOL for NP0073739 ((+)-Smilaside J)

3D MOL for NP0073739 ((+)-Smilaside J)

3D SDF for NP0073739 ((+)-Smilaside J)

3D-SDF for NP0073739 ((+)-Smilaside J)

PDB for NP0073739 ((+)-Smilaside J)

3D PDB for NP0073739 ((+)-Smilaside J)

SMILES for NP0073739 ((+)-Smilaside J)

INCHI for NP0073739 ((+)-Smilaside J)

Structure for NP0073739 ((+)-Smilaside J)

3D Structure for NP0073739 ((+)-Smilaside J)