NP-MRD: Showing NP-Card for (2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0219004)

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Record Information

Version

2.0

Created at

2022-09-05 19:51:18 UTC

Updated at

2022-09-05 19:51:18 UTC

NP-MRD ID

NP0219004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

(2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Durio zibethinus. Based on a literature review very few articles have been published on (2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221512D          

 53 56  0  0  1  0            999 V2000
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -2.8579   -4.1250    0.0000 C   0  0  0  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
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    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
    1.4289   -7.4250    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
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 16 24  1  0  0  0  0
  9 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 43 46  2  0  0  0  0
 38 46  1  0  0  0  0
 29 47  1  0  0  0  0
 47 48  2  0  0  0  0
 26 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  6 51  1  0  0  0  0
 51 52  2  0  0  0  0
  3 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END


  Mrv1652309052221512D          

 53 56  0  0  1  0            999 V2000
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -2.8579   -4.1250    0.0000 C   0  0  0  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
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    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
    1.4289   -7.4250    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
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
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 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
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 41 42  1  0  0  0  0
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 38 46  1  0  0  0  0
 29 47  1  0  0  0  0
 47 48  2  0  0  0  0
 26 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  6 51  1  0  0  0  0
 51 52  2  0  0  0  0
  3 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)[C@@H](O)[C@H](COC(=O)\C=C\C1=CC=C(O)C(OC)=C1)OC1=CC=C(CCCOC(=O)\C=C\C2=CC=C(O)C(OC)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C40H42O13/c1-47-32-16-12-28(23-31(32)43)40(46)37(24-52-39(45)18-11-27-8-14-30(42)35(21-27)49-3)53-33-15-9-25(22-36(33)50-4)6-5-19-51-38(44)17-10-26-7-13-29(41)34(20-26)48-2/h7-18,20-23,37,40-43,46H,5-6,19,24H2,1-4H3/b17-10+,18-11+/t37-,40+/m0/s1

> <INCHI_KEY>
KKLMVWZOQVHRCK-MOLXBTQUSA-N

> <FORMULA>
C40H42O13

> <MOLECULAR_WEIGHT>
730.763

> <EXACT_MASS>
730.262541412

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
77.97034475945446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
6.771658294666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.841523491972433

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.36274988696275

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5208525569268954

> <JCHEM_POLAR_SURFACE_AREA>
179.66999999999996

> <JCHEM_REFRACTIVITY>
196.16159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -6.930   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      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.669  -4.620   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      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   52                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   51                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   16                                                       
CONECT   25    9   26                                                       
CONECT   26   25   27   48                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   47                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   46                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   43   38                                                       
CONECT   47   29   48                                                       
CONECT   48   47   26   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51    6   52                                                       
CONECT   52   51    3   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-3-Hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₄₀H₄₂O₁₃

Average Mass

730.7630 Da

Monoisotopic Mass

730.26254 Da

IUPAC Name

(2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(2S,3R)-3-hydroxy-2-[4-(3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1O)[C@@H](O)[C@H](COC(=O)\C=C\C1=CC=C(O)C(OC)=C1)OC1=CC=C(CCCOC(=O)\C=C\C2=CC=C(O)C(OC)=C2)C=C1OC

InChI Identifier

InChI=1S/C40H42O13/c1-47-32-16-12-28(23-31(32)43)40(46)37(24-52-39(45)18-11-27-8-14-30(42)35(21-27)49-3)53-33-15-9-25(22-36(33)50-4)6-5-19-51-38(44)17-10-26-7-13-29(41)34(20-26)48-2/h7-18,20-23,37,40-43,46H,5-6,19,24H2,1-4H3/b17-10+,18-11+/t37-,40+/m0/s1

InChI Key

KKLMVWZOQVHRCK-MOLXBTQUSA-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
Durio zibethinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Neolignan skeleton
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Aromatic alcohol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.77	ChemAxon
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	179.67 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	196.16 m³·mol⁻¹	ChemAxon
Polarizability	77.97 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

163188172

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)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0219004)

MOL for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0219004 ((2s,3r)-3-hydroxy-2-[4-(3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propyl)-2-methoxyphenoxy]-3-(3-hydroxy-4-methoxyphenyl)propyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)