NP-MRD: Showing NP-Card for (1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0283204)

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Record Information

Version

2.0

Created at

2022-09-09 10:22:04 UTC

Updated at

2022-09-09 10:22:05 UTC

NP-MRD ID

NP0283204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

Nigrumin 5-ferulate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Ribes nigrum. Based on a literature review very few articles have been published on Nigrumin 5-ferulate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212222D          

 31 32  0  0  1  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  2  0  0  0  0
 14 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
  5 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
    7.9252    1.9704   -1.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4993    0.7254   -1.2222 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7225   -0.2836   -0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3749   -0.1097   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033   -1.1095    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978   -0.9743    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056    0.1266    0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906    0.1643    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    1.2046    0.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -0.9308    1.1397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.8806    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575   -0.4619    2.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5277   -0.1402    3.8810 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787   -1.1905    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014   -1.1056    1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314   -0.1894    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2772   -0.0311    0.5681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0193   -0.4083   -0.5489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3437    0.0096   -0.4588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0932   -0.6025   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5724   -0.2067   -2.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4730    1.5105   -0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2543    2.0540    0.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632    2.0771   -0.3764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2973    1.5955   -1.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200    1.4197    0.8858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4889    1.5136    1.8721 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2264   -2.3180    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733   -2.5352    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -1.5018   -0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6485   -1.7497   -0.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6811    2.5502   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0070    1.8734   -2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7195    2.5140   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318    0.8493   -0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.8425    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9916    0.9865   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -1.5044   -0.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3502   -0.7609    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.1171    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4898   -0.7033    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7567   -0.4025    0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0607   -1.7123   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1689   -0.2952   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9525   -0.8491   -3.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8142    1.8274   -1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7202    1.3565    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0749    3.1734   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390    1.7724   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5876    1.9609    1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0782    1.3167    2.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -3.1448    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0344   -3.4928    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1984   -0.9977   -1.0771 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
  8 10  1  0
 10 11  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
 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
 11 12  1  0
 12 13  3  0
  5 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30  3  1  0
 26 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  1
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  1
 25 49  1  0
 26 50  1  1
 27 51  1  0
 28 52  1  0
 29 53  1  0
 31 54  1  0
M  END


  Mrv1652309092212222D          

 31 32  0  0  1  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  2  0  0  0  0
 14 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
  5 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O\C(=C\CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C#N)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO10/c1-28-14-8-11(2-4-13(14)23)3-5-16(24)30-12(9-21)6-7-29-20-19(27)18(26)17(25)15(10-22)31-20/h2-6,8,15,17-20,22-23,25-27H,7,10H2,1H3/b5-3+,12-6+/t15-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
DKQMEWWZMHRGFF-VEDLHWAYSA-N

> <FORMULA>
C20H23NO10

> <MOLECULAR_WEIGHT>
437.401

> <EXACT_MASS>
437.132195945

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.386791256555455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E)-1-cyano-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.3837116466666659

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.211723080127793

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.698800012338985

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835511808698

> <JCHEM_POLAR_SURFACE_AREA>
178.92999999999998

> <JCHEM_REFRACTIVITY>
106.11140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-1-cyano-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.668 -17.710   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337 -21.560   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336 -25.410   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   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                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Nigrumin 5-ferulic acid	Generator

Chemical Formula

C₂₀H₂₃NO₁₀

Average Mass

437.4010 Da

Monoisotopic Mass

437.13220 Da

IUPAC Name

(1E)-1-cyano-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(1E)-1-cyano-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O\C(=C\CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C#N)=CC=C1O

InChI Identifier

InChI=1S/C20H23NO10/c1-28-14-8-11(2-4-13(14)23)3-5-16(24)30-12(9-21)6-7-29-20-19(27)18(26)17(25)15(10-22)31-20/h2-6,8,15,17-20,22-23,25-27H,7,10H2,1H3/b5-3+,12-6+/t15-,17-,18+,19-,20-/m1/s1

InChI Key

DKQMEWWZMHRGFF-VEDLHWAYSA-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
Ribes nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Coumaric acid or derivatives
Cinnamic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen 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	-0.38	ChemAxon
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.93 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.11 m³·mol⁻¹	ChemAxon
Polarizability	43.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

102372418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0283204)

MOL for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0283204 ((1e)-1-cyano-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}prop-1-en-1-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)