NP-MRD: Showing NP-Card for (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid (NP0310134)

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Record Information

Version

2.0

Created at

2022-09-11 05:13:34 UTC

Updated at

2022-09-11 05:13:35 UTC

NP-MRD ID

NP0310134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Description

4-O-beta-D-glucosyl-trans-sinapic acid, also known as 4-O-(b-D-glucopyranosyl)-(2E)-sinapate or sinapoyl-4-O-beta-D-glucoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid is found in Brassica napus, Cydonia oblonga and Salacia chinensis. Based on a literature review very few articles have been published on 4-O-beta-D-glucosyl-trans-sinapic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207132D          

 27 28  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
    1.9949    1.5540    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944    0.6797    2.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083    0.0434    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660    0.2838    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2587   -0.3035   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6095   -0.0008   -1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1449   -0.5130   -2.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5116   -0.1734   -2.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9626   -0.6971   -3.7194 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3252    0.6967   -1.9752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976   -1.1568   -1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072   -1.4216   -0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -2.3007   -1.6029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -2.9007   -2.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528   -0.8246    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.0587    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669   -0.3129    0.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1257    0.4256    1.6859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    1.3108    1.3197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3031    2.4555    2.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6550    2.0058    3.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3911    0.4807    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5012    1.2822    1.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711   -0.3572   -0.0582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2643   -1.1669   -0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015   -1.1334    0.0206 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5940   -1.5080   -1.3090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657    2.4942    2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957    1.0709    2.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6022    1.8212    3.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446    0.9611    0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2438    0.6981   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708   -1.1961   -2.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4137    0.7255   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212   -1.6467   -2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -3.4828   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -3.6064   -2.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -2.1164   -3.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5076    0.4568   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477    1.7152    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3706    3.0137    2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0834    3.1162    1.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9487    2.7610    4.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5052   -0.2155    2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464    1.7417    1.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    0.3813   -0.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7161   -1.3472    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -2.0979    0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979   -0.6369   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15  3  1  0
 26 17  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 11 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  6
 19 40  1  6
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  1
 23 45  1  0
 24 46  1  6
 25 47  1  0
 26 48  1  1
 27 49  1  0
M  END


  Mrv1652309112207132D          

 27 28  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0310134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1

> <INCHI_KEY>
KKLWTTVTWMTNBP-KYXYLJOWSA-N

> <FORMULA>
C17H22O10

> <MOLECULAR_WEIGHT>
386.353

> <EXACT_MASS>
386.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.56224883271952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <JCHEM_LOGP>
-0.7508896863333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.199887077962922

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4645079828135703

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092366207709

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
90.11160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
4-O-(beta-D-Glucopyranosyl)-(2E)-sinapic acid	ChEBI
4-O-(beta-D-Glucosyl)-(2E)-sinapic acid	ChEBI
O(4)-(beta-D-Glucosyl)-(2E)-sinapic acid	ChEBI
Sinapoyl-4-O-beta-D-glucoside	ChEBI
4-O-(b-D-Glucopyranosyl)-(2E)-sinapate	Generator
4-O-(b-D-Glucopyranosyl)-(2E)-sinapic acid	Generator
4-O-(beta-D-Glucopyranosyl)-(2E)-sinapate	Generator
4-O-(Β-D-glucopyranosyl)-(2E)-sinapate	Generator
4-O-(Β-D-glucopyranosyl)-(2E)-sinapic acid	Generator
4-O-(b-D-Glucosyl)-(2E)-sinapate	Generator
4-O-(b-D-Glucosyl)-(2E)-sinapic acid	Generator
4-O-(beta-D-Glucosyl)-(2E)-sinapate	Generator
4-O-(Β-D-glucosyl)-(2E)-sinapate	Generator
4-O-(Β-D-glucosyl)-(2E)-sinapic acid	Generator
O(4)-(b-D-Glucosyl)-(2E)-sinapate	Generator
O(4)-(b-D-Glucosyl)-(2E)-sinapic acid	Generator
O(4)-(beta-D-Glucosyl)-(2E)-sinapate	Generator
O(4)-(Β-D-glucosyl)-(2E)-sinapate	Generator
O(4)-(Β-D-glucosyl)-(2E)-sinapic acid	Generator
Sinapoyl-4-O-b-D-glucoside	Generator
Sinapoyl-4-O-β-D-glucoside	Generator
4-O-b-D-Glucosyl-trans-sinapate	Generator
4-O-b-D-Glucosyl-trans-sinapic acid	Generator
4-O-beta-D-Glucosyl-trans-sinapate	Generator
4-O-Β-D-glucosyl-trans-sinapate	Generator
4-O-Β-D-glucosyl-trans-sinapic acid	Generator

Chemical Formula

C₁₇H₂₂O₁₀

Average Mass

386.3530 Da

Monoisotopic Mass

386.12130 Da

IUPAC Name

(2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1

InChI Key

KKLWTTVTWMTNBP-KYXYLJOWSA-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
Brassica napus	LOTUS Database	35616633
Cydonia oblonga	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Anisole
Styrene
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Oxane
Benzenoid
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Hydrocarbon derivative
Primary alcohol
Alcohol
Carbonyl group
Organic oxide
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	-0.75	ChemAxon
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.11 m³·mol⁻¹	ChemAxon
Polarizability	37.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

4444179

KEGG Compound ID

C02919

BioCyc ID

1-SINAPOYL-D-GLUCOSE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280550

PDB ID

Not Available

ChEBI ID

145341

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid (NP0310134)

MOL for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D MOL for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D SDF for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D-SDF for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

PDB for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D PDB for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

SMILES for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

INCHI for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

Structure for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D Structure for NP0310134 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)