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-enal (NP0326459)

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Record Information

Version

1.0

Created at

2022-09-12 08:01:39 UTC

Updated at

2022-09-12 08:01:40 UTC

NP-MRD ID

NP0326459

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-enal

Description

(E)-sinapaldehyde 4-O-beta-D-glucopyranoside, also known as 4-O-(beta-D-glucosyl)-4-trans-sinapoyl aldehyde or sinapaldehyde 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 (E)-sinapaldehyde 4-O-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal is found in Cistanche tubulosa, Eleutherococcus senticosus, Magnolia officinalis, Magnolia champaca, Phellodendron amurense and Syringa reticulata. It was first documented in 2005 (PMID: 15907484). Based on a literature review a small amount of articles have been published on (E)-sinapaldehyde 4-O-beta-D-glucopyranoside (PMID: 25132792) (PMID: 25104900).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210012D          

 26 27  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
   -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
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
    1.1131    3.4940    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5884    2.2015    0.7638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3411    1.0839    0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    1.1936    0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    0.1048    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434    0.3254   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317   -0.6021   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2574   -0.2961   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0870   -1.1921   -0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193   -1.1059   -0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351   -1.2333    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9692   -2.4668   -0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603   -3.5992   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -0.1385    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -0.1977    0.5324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850   -0.0529   -0.4950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3479    1.0966   -0.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6741    0.8995   -0.7550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3578    2.2408   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687    2.9546    0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139    0.0133    0.2656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6840   -0.1410    0.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6353   -1.3379    0.1936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2978   -1.6888    1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3729   -1.3061   -0.6243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6353   -1.6238   -1.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677    4.1974    1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561    3.4925    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382    3.7995    0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    2.1653    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3444    1.3425    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -1.6171   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6039    0.7232   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294   -1.9924   -0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1697   -4.5193   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5717   -3.7456    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827   -3.4008   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916    0.0952   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500    0.4179   -1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    2.7816   -1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4350    2.0149   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434    3.0010    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    0.5044    1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2095    0.1946    0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571   -2.0811   -0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3352   -2.6746    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453   -2.1560   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -1.1690   -2.4930 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  9  2  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14  3  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  6
 18 39  1  6
 19 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  1
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  1
 26 48  1  0
M  END


  Mrv1652309122210012D          

 26 27  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
   -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
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0326459

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-7,12-15,17,19-22H,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1

> <INCHI_KEY>
OYTCTPHTVUEGCL-GCPOEHJPSA-N

> <FORMULA>
C17H22O9

> <MOLECULAR_WEIGHT>
370.354

> <EXACT_MASS>
370.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.572829424325015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <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-enal

> <JCHEM_LOGP>
-0.9095059386666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.195995667730958

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.19988707724474

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092366207709

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
89.18620000000003

> <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-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -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  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  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   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
(e)-Sinapaldehyde glucopyranoside	ChEBI
(e)-Sinapic aldehyde 4-O-beta-D-glucopyranoside	ChEBI
(e)-Sinapyl aldehyde 4-O-beta-D-glucopyranoside	ChEBI
4-O-(beta-D-Glucosyl)-4-trans-sinapoyl aldehyde	ChEBI
4-O-(beta-D-Glucosyl)-trans-sinapyl aldehyde	ChEBI
Sinapaldehyde glucoside	ChEBI
Sinapic aldehyde glucoside	ChEBI
Sinapyl aldehyde glucoside	ChEBI
trans-4-O-(beta-D-Glucosyl)-sinapoyl aldehyde	ChEBI
trans-Sinapaldehyde 4-O-beta-D-glucopyranoside	ChEBI
trans-Sinapaldehyde beta-D-glucoside	ChEBI
trans-Sinapaldehyde glucoside	ChEBI
trans-Sinapic aldehyde 4-O-beta-D-glucopyranoside	ChEBI
trans-Sinapyl aldehyde 4-O-beta-D-glucopyranoside	ChEBI
(e)-Sinapic aldehyde 4-O-b-D-glucopyranoside	Generator
(e)-Sinapic aldehyde 4-O-β-D-glucopyranoside	Generator
(e)-Sinapyl aldehyde 4-O-b-D-glucopyranoside	Generator
(e)-Sinapyl aldehyde 4-O-β-D-glucopyranoside	Generator
4-O-(b-D-Glucosyl)-4-trans-sinapoyl aldehyde	Generator
4-O-(Β-D-glucosyl)-4-trans-sinapoyl aldehyde	Generator
4-O-(b-D-Glucosyl)-trans-sinapyl aldehyde	Generator
4-O-(Β-D-glucosyl)-trans-sinapyl aldehyde	Generator
trans-4-O-(b-D-Glucosyl)-sinapoyl aldehyde	Generator
trans-4-O-(Β-D-glucosyl)-sinapoyl aldehyde	Generator
trans-Sinapaldehyde 4-O-b-D-glucopyranoside	Generator
trans-Sinapaldehyde 4-O-β-D-glucopyranoside	Generator
trans-Sinapaldehyde b-D-glucoside	Generator
trans-Sinapaldehyde β-D-glucoside	Generator
trans-Sinapic aldehyde 4-O-b-D-glucopyranoside	Generator
trans-Sinapic aldehyde 4-O-β-D-glucopyranoside	Generator
trans-Sinapyl aldehyde 4-O-b-D-glucopyranoside	Generator
trans-Sinapyl aldehyde 4-O-β-D-glucopyranoside	Generator
(e)-Sinapaldehyde 4-O-b-D-glucopyranoside	Generator
(e)-Sinapaldehyde 4-O-β-D-glucopyranoside	Generator

Chemical Formula

C₁₇H₂₂O₉

Average Mass

370.3540 Da

Monoisotopic Mass

370.12638 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-enal

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-enal

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H22O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-7,12-15,17,19-22H,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1

InChI Key

OYTCTPHTVUEGCL-GCPOEHJPSA-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
Cistanche tubulosa	LOTUS Database	35616633
Eleutherococcus senticosus	LOTUS Database	35616633
Magnolia officinalis	LOTUS Database	35616633
Michelia champaca	LOTUS Database	35616633
Phellodendron amurense	LOTUS Database	35616633
Syringa reticulata	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
O-glycosyl compound
Cinnamaldehyde
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Enal
Alpha,beta-unsaturated aldehyde
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Polyol
Aldehyde
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary 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	-0.91	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	89.19 m³·mol⁻¹	ChemAxon
Polarizability	36.57 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

C00060096

Chemspider ID

22913075

KEGG Compound ID

Not Available

BioCyc ID

CPD-79

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25791064

PDB ID

Not Available

ChEBI ID

142126

Good Scents ID

Not Available

References

General References

Wang C, Chao Z, Sun W, Wu X, Ito Y: ISOLATION OF GLYCOSIDES FROM THE BARKS OF ILEX ROTUNDA BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY. J Liq Chromatogr Relat Technol. 2014 Apr 1;37(16):2363-2376. doi: 10.1080/10826076.2013.832297. [PubMed:25132792 ]
Wang C, Chao Z, Sun W, Wu X, Ito Y: Enrichment and purification of pedunculoside and syringin from the barks of Ilex rotunda with macroporous resins. J Liq Chromatogr Relat Technol. 2014 Feb 1;37(4):572-587. doi: 10.1080/10826076.2012.749499. [PubMed:25104900 ]
Lim EK, Jackson RG, Bowles DJ: Identification and characterisation of Arabidopsis glycosyltransferases capable of glucosylating coniferyl aldehyde and sinapyl aldehyde. FEBS Lett. 2005 May 23;579(13):2802-6. doi: 10.1016/j.febslet.2005.04.016. Epub 2005 Apr 25. [PubMed:15907484 ]
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-enal (NP0326459)

MOL for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

3D MOL for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

3D SDF for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

3D-SDF for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

PDB for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

3D PDB for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

SMILES for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

INCHI for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

Structure for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)

3D Structure for NP0326459 ((2e)-3-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enal)