NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate (NP0223675)

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Record Information

Version

2.0

Created at

2022-09-06 01:50:17 UTC

Updated at

2022-09-06 01:50:17 UTC

NP-MRD ID

NP0223675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate

Description

(E)-3,4-Dihydroxy-5-methoxycinnamoyl 6-O-[2-O-[(E)-3,4-dihydroxy-5-methoxycinnamoyl]-beta-D-glucopyranosyl]-beta-D-glucopyranoside belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. (2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate is found in Sabia japonica. Based on a literature review very few articles have been published on (E)-3,4-Dihydroxy-5-methoxycinnamoyl 6-O-[2-O-[(E)-3,4-dihydroxy-5-methoxycinnamoyl]-beta-D-glucopyranosyl]-beta-D-glucopyranoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203502D          

 51 54  0  0  1  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    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    3.3000    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
   -0.0000    3.3000    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    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
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    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
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
 31 40  1  0  0  0  0
 13 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 11 45  1  0  0  0  0
 45 46  1  1  0  0  0
  5 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
  3 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END


  Mrv1652309062203502D          

 51 54  0  0  1  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    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    3.3000    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
   -0.0000    3.3000    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    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
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    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
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
 31 40  1  0  0  0  0
 13 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 11 45  1  0  0  0  0
 45 46  1  1  0  0  0
  5 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
  3 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223675

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H38O19/c1-45-17-9-13(7-15(34)23(17)38)3-5-21(36)50-30-28(43)25(40)19(11-33)48-32(30)47-12-20-26(41)27(42)29(44)31(49-20)51-22(37)6-4-14-8-16(35)24(39)18(10-14)46-2/h3-10,19-20,25-35,38-44H,11-12H2,1-2H3/b5-3+,6-4+/t19-,20-,25-,26-,27+,28+,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
HHPKRDZARJAVJF-RQECULSDSA-N

> <FORMULA>
C32H38O19

> <MOLECULAR_WEIGHT>
726.637

> <EXACT_MASS>
726.200729004

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
70.62121305622033

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.165197245666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.730084412471195

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.129123894122744

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491070829825425

> <JCHEM_POLAR_SURFACE_AREA>
301.05

> <JCHEM_REFRACTIVITY>
168.32210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   50                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   47                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   45                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   41                                                  
CONECT   14   13   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   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   31                                                       
CONECT   41   13   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   11   46                                                  
CONECT   46   45                                                            
CONECT   47    5   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48    3   51                                                  
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

View in JSmol

Synonyms

Value	Source
(e)-3,4-Dihydroxy-5-methoxycinnamoyl 6-O-[2-O-[(e)-3,4-dihydroxy-5-methoxycinnamoyl]-b-D-glucopyranosyl]-b-D-glucopyranoside	Generator
(e)-3,4-Dihydroxy-5-methoxycinnamoyl 6-O-[2-O-[(e)-3,4-dihydroxy-5-methoxycinnamoyl]-β-D-glucopyranosyl]-β-D-glucopyranoside	Generator

Chemical Formula

C₃₂H₃₈O₁₉

Average Mass

726.6370 Da

Monoisotopic Mass

726.20073 Da

IUPAC Name

(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-3-{[(2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)\C=C\C3=CC(O)=C(O)C(OC)=C3)[C@@H](O)[C@H](O)[C@H]2O)=CC(O)=C1O

InChI Identifier

InChI=1S/C32H38O19/c1-45-17-9-13(7-15(34)23(17)38)3-5-21(36)50-30-28(43)25(40)19(11-33)48-32(30)47-12-20-26(41)27(42)29(44)31(49-20)51-22(37)6-4-14-8-16(35)24(39)18(10-14)46-2/h3-10,19-20,25-35,38-44H,11-12H2,1-2H3/b5-3+,6-4+/t19-,20-,25-,26-,27+,28+,29-,30-,31+,32-/m1/s1

InChI Key

HHPKRDZARJAVJF-RQECULSDSA-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
Sabia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Anisole
Catechol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Carboxylic acid derivative
Ether
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	-0.17	ChemAxon
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	301.05 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	168.32 m³·mol⁻¹	ChemAxon
Polarizability	70.62 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

24827808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate (NP0223675)

MOL for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

3D MOL for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

3D SDF for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

PDB for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

3D PDB for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

SMILES for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

INCHI for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

Structure for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)

3D Structure for NP0223675 ((2s,3r,4s,5s,6r)-6-({[(2r,3r,4s,5s,6r)-3-{[(2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate)