NP-MRD: Showing NP-Card for (+)-Smilaside I (NP0073738)

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Record Information

Version

2.0

Created at

2022-04-28 18:57:48 UTC

Updated at

2022-04-28 18:57:48 UTC

NP-MRD ID

NP0073738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Smilaside I

Description

[(2S,3S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)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 I is found in Smilax bracteata. Based on a literature review very few articles have been published on [(2S,3S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220572D          

 61 65  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  1  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
    2.1030   -5.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980   -5.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4966   -2.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1465   -2.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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   -0.3188   -5.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  6  0  0  0
  9 19  1  1  0  0  0
  8 20  1  6  0  0  0
  4 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
  3 34  1  6  0  0  0
  2 35  1  1  0  0  0
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  1 47  1  6  0  0  0
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 53 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 56 61  1  0  0  0  0
M  END

     RDKit          3D

105109  0  0  0  0  0  0  0  0999 V2000
    2.0348   -0.1861   -5.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844   -1.2084   -6.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970   -1.8975   -6.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -1.5913   -5.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -2.2639   -4.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -1.9015   -3.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1435   -1.8430   -2.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0073738

> <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=C3)(O[C@H]3O[C@H](COC(C)=O)[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/C42H44O19/c1-23(43)55-20-31-36(50)37(51)38(52)41(58-31)61-42(22-57-34(48)16-8-24-3-11-27(44)12-4-24)40(53)39(59-35(49)18-9-25-5-13-28(45)14-6-25)32(60-42)21-56-33(47)17-10-26-7-15-29(46)30(19-26)54-2/h3-19,31-32,36-41,44-46,50-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37+,38-,39-,40+,41-,42+/m1/s1

> <INCHI_KEY>
YWTCWUMCRKCKAD-HFNOVLTQSA-N

> <FORMULA>
C42H44O19

> <MOLECULAR_WEIGHT>
852.795

> <EXACT_MASS>
852.247679197

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
85.81200439469629

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.945595370000001

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.54126223345979

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.028855221879299

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490874695413797

> <JCHEM_POLAR_SURFACE_AREA>
283.72999999999996

> <JCHEM_REFRACTIVITY>
209.03459999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxy-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)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  C   UNK     0       3.926  -9.632   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.170 -10.973   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.466  -9.615   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.114  -5.639   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.546  -2.988   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.534  -3.020   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.558  -5.703   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.098  -5.687   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.854  -4.346   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.070  -3.020   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.394  -4.329   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.150  -2.988   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.690  -2.972   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.473  -4.297   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.013  -4.281   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.769  -2.939   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.985  -1.614   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.446  -1.630   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -15.309  -2.923   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.512  -7.474   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.477 -10.661   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.009 -10.500   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.635  -9.093   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.914 -11.746   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.445 -11.585   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -10.351 -12.831   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -9.724 -14.237   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.629 -15.483   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -12.161 -15.322   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -12.787 -13.915   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -11.882 -12.670   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -13.066 -16.568   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -2.127 -10.661   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -0.595 -10.500   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.310 -11.746   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -0.316 -13.152   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       1.842 -11.585   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.747 -12.831   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.278 -12.670   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.905 -11.263   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.436 -11.102   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.342 -12.348   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.715 -13.754   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.184 -13.915   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       7.620 -15.000   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       6.994 -16.407   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       8.873 -12.187   0.000  0.00  0.00           O+0
CONECT    1    2    5   47                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5    6   21                                             
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10                                                            
CONECT   19    9                                                            
CONECT   20    8                                                            
CONECT   21    4   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34    3                                                            
CONECT   35    2   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
CONECT   46   43                                                            
CONECT   47    1   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   61                                                  
CONECT   57   56   58   59                                                  
CONECT   58   57   53                                                       
CONECT   59   57   60                                                       
CONECT   60   59                                                            
CONECT   61   56                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  130    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₂H₄₄O₁₉

Average Mass

852.7950 Da

Monoisotopic Mass

852.24768 Da

IUPAC Name

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=C3)(O[C@H]3O[C@H](COC(C)=O)[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/C42H44O19/c1-23(43)55-20-31-36(50)37(51)38(52)41(58-31)61-42(22-57-34(48)16-8-24-3-11-27(44)12-4-24)40(53)39(59-35(49)18-9-25-5-13-28(45)14-6-25)32(60-42)21-56-33(47)17-10-26-7-15-29(46)30(19-26)54-2/h3-19,31-32,36-41,44-46,50-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37+,38-,39-,40+,41-,42+/m1/s1

InChI Key

YWTCWUMCRKCKAD-HFNOVLTQSA-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

Tetracarboxylic acid or derivatives
Coumaric acid ester
Cinnamic acid ester
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
C-glycosyl compound
Methoxyphenol
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
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	3.12	ALOGPS
logP	3.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	283.73 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	209.03 m³·mol⁻¹	ChemAxon
Polarizability	85.81 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

162821222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Smilaside I (NP0073738)

MOL for NP0073738 ((+)-Smilaside I)

3D MOL for NP0073738 ((+)-Smilaside I)

3D SDF for NP0073738 ((+)-Smilaside I)

3D-SDF for NP0073738 ((+)-Smilaside I)

PDB for NP0073738 ((+)-Smilaside I)

3D PDB for NP0073738 ((+)-Smilaside I)

SMILES for NP0073738 ((+)-Smilaside I)

INCHI for NP0073738 ((+)-Smilaside I)

Structure for NP0073738 ((+)-Smilaside I)

3D Structure for NP0073738 ((+)-Smilaside I)