NP-MRD: Showing NP-Card for (+)-Smilaside B (NP0078751)

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Record Information

Version

2.0

Created at

2022-04-28 23:49:17 UTC

Updated at

2022-04-28 23:49:17 UTC

NP-MRD ID

NP0078751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Smilaside B

Description

[(2R,3R,4S,5S)-5-{[(2R,3R,4S,5R,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-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 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. (+)-Smilaside B is found in Smilax china . Based on a literature review very few articles have been published on [(2R,3R,4S,5S)-5-{[(2R,3R,4S,5R,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-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

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201492D          

 52 55  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
    0.4531   -5.1771    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
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   -4.8865   -4.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3719   -6.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9866   -6.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0823   -8.0359    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
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  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  4 21  1  1  0  0  0
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  3 23  1  6  0  0  0
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 32 33  2  0  0  0  0
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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
  2 37  1  1  0  0  0
  1 38  1  6  0  0  0
 38 39  1  0  0  0  0
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 44 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 47 52  1  0  0  0  0
M  END

     RDKit          3D

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    0.8841    1.8378    2.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 69  1  0
 23 70  1  6
 24 71  1  0
 25 72  1  1
 26 73  1  0
 27 74  1  1
 30 75  1  0
 30 76  1  0
 30 77  1  0
 32 78  1  1
 36 79  1  0
 37 80  1  0
 39 81  1  0
 40 82  1  0
 42 83  1  0
 45 84  1  0
 45 85  1  0
 45 86  1  0
 46 87  1  0
 47 88  1  1
 48 89  1  0
 49 90  1  0
 50 91  1  0
 52 92  1  0
M  END


  Mrv1652304292201492D          

 52 55  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
    0.4531   -5.1771    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
   -1.6467   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0517   -2.3452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0666   -0.9164    0.0000 C   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
   -3.4888   -4.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865   -4.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303   -5.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5434   -5.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719   -6.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -6.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -7.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0288   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135   -8.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9850   -7.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -8.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2550   -9.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8573   -9.1430    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
   -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
    0.9866   -6.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715   -6.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920   -6.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.9330   -6.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974   -7.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  4 21  1  1  0  0  0
 21 22  1  0  0  0  0
  3 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
  2 37  1  1  0  0  0
  1 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 47 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](CO)(O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3OC(C)=O)[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(37)48-31-30(44)28(42)24(14-35)49-33(31)52-34(16-36)32(50-27(41)11-7-19-5-9-21(39)23(13-19)46-3)29(43)25(51-34)15-47-26(40)10-6-18-4-8-20(38)22(12-18)45-2/h4-13,24-25,28-33,35-36,38-39,42-44H,14-16H2,1-3H3/b10-6+,11-7+/t24-,25-,28+,29-,30+,31-,32+,33-,34+/m1/s1

> <INCHI_KEY>
XLHWVVGQWRFHPR-XRTZUJPISA-N

> <FORMULA>
C34H40O18

> <MOLECULAR_WEIGHT>
736.676

> <EXACT_MASS>
736.221464448

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
72.78290759330004

> <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,5R,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-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

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.0575987080000002

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.167107240941716

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.56616229646371

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810855582593705

> <JCHEM_POLAR_SURFACE_AREA>
266.6599999999999

> <JCHEM_REFRACTIVITY>
173.9492

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5S)-5-{[(2R,3R,4S,5R,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-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       0.846  -9.664   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      -3.074  -3.036   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.830  -4.378   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.858  -1.711   0.000  0.00  0.00           C+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  O   UNK     0      -6.512  -7.474   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.657  -8.505   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.121  -8.029   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.337 -10.011   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.481 -11.042   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.161 -12.548   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.696 -13.024   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.376 -14.530   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.521 -15.561   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.985 -15.085   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.305 -13.578   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.130 -16.115   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -9.809 -17.622   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.200 -17.067   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.477 -10.661   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.127 -10.661   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.595 -10.500   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.310 -11.746   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.316 -13.152   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.842 -11.585   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.747 -12.831   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.278 -12.670   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.905 -11.263   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.436 -11.102   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.342 -12.348   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.715 -13.754   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.184 -13.915   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       7.620 -15.000   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       6.994 -16.407   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.873 -12.187   0.000  0.00  0.00           O+0
CONECT    1    2    5   38                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6   21                                             
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   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31                                                            
CONECT   37    2                                                            
CONECT   38    1   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48   44                                                       
CONECT   50   48   51                                                       
CONECT   51   50                                                            
CONECT   52   47                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5S)-5-{[(2R,3R,4S,5R,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-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-enoic acid	Generator

Chemical Formula

C₃₄H₄₀O₁₈

Average Mass

736.6760 Da

Monoisotopic Mass

736.22146 Da

IUPAC Name

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

InChI Key

XLHWVVGQWRFHPR-XRTZUJPISA-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 china	Plant	KNApSAcK

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

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
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	1.49	ALOGPS
logP	1.06	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-3	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	72.78 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

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

162927071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Smilaside B (NP0078751)

MOL for NP0078751 ((+)-Smilaside B)

3D MOL for NP0078751 ((+)-Smilaside B)

3D SDF for NP0078751 ((+)-Smilaside B)

3D-SDF for NP0078751 ((+)-Smilaside B)

PDB for NP0078751 ((+)-Smilaside B)

3D PDB for NP0078751 ((+)-Smilaside B)

SMILES for NP0078751 ((+)-Smilaside B)

INCHI for NP0078751 ((+)-Smilaside B)

Structure for NP0078751 ((+)-Smilaside B)

3D Structure for NP0078751 ((+)-Smilaside B)