NP-MRD: Showing NP-Card for Secoisolariciresinol (NP0044237)

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Record Information

Version

1.0

Created at

2022-02-14 20:33:31 UTC

Updated at

2022-03-10 22:22:27 UTC

NP-MRD ID

NP0044237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Secoisolariciresinol

Description

Secoisolariciresinol belongs to the class of organic compounds known as dibenzylbutanediol lignans, which contain a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is an essentially neutral compound. Its highest known food content (0.3%) Is in flaxseed (Linum usitat∆í¬±ssimum) while the water extract of silver fir wood contains more than 5% secoisolariciresinol (PMID: 15877880 ). It is also present in nettle brew and cannabis plants (PMID: 6991645 ). Secoisolariciresinol has been detected in sourdoughs, lindens, savoy cabbages, sugar apples, and common grapes, making secoisolariciresinol a potential biomarker for the consumption of these foods. In the intestine, the gut microflora can form secoisolariciresinol from the secoisolariciresinol diglucoside (also in flaxseed) and it can then be further transformed into the enterolignan enterodiol. Epidemiological studies showed associations between secoisolariciresinol intake and decreased risk of cardiovascular disease (PMID: 29101172 )..

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302142221332D          

 26 27  0  0  1  0            999 V2000
   -2.8579   -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
   -1.4289   -2.4750    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
   -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
    1.4289   -2.4750    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
    2.1434   -2.8875    0.0000 C   0  0  2  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 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
    3.5724   -2.8875    0.0000 C   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
    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
    5.7158   -1.6500    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
    5.7158   -4.1250    0.0000 O   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
    3.5724   -3.7125    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
  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 17 25  1  0  0  0  0
  8 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
    4.7508    0.8490   -2.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221    1.7239   -1.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6936    1.3364   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167    0.0582   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944   -0.3157    1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717   -1.6411    1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111   -2.1169    0.7468 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4523   -3.5206    1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561   -4.3502    0.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944   -1.2711    0.8168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6757   -2.0424    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3265   -2.3195   -1.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -0.0427   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6457    0.7441    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.6282    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604    2.3913    1.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507    2.3203    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0919    3.0967    0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517    1.4495   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247    1.3533   -1.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8530    0.4550   -2.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7264    0.6860   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672    0.6986    2.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    1.9713    1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    2.3024    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943    3.6131    0.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487    0.7315   -3.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -0.1111   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246    1.2856   -2.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -0.6894   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -2.3633    1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -1.8569    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158   -2.2938   -0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515   -3.5725    2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932   -4.0353    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954   -4.3406   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -0.9159    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5925   -1.4000    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -2.9777    0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749   -2.3133   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    0.6303    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -0.3873   -1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.7165    1.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361    3.0808    2.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8479    2.9917    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    0.6065   -3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177    0.6455   -3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8235   -0.5978   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    0.0117   -1.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7041    0.4583    2.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131    2.7135    2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    3.9258   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 23  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 22  2  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
  5  4  2  0
  4  3  1  0
 15 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 52  1  0
 24 51  1  0
 23 50  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 22 49  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 18 45  1  0
 16 44  1  0
 15 43  1  0
  4 30  1  0
M  END


  Mrv1652302142221332D          

 26 27  0  0  1  0            999 V2000
   -2.8579   -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
   -1.4289   -2.4750    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
   -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
    1.4289   -2.4750    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
    2.1434   -2.8875    0.0000 C   0  0  2  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 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
    3.5724   -2.8875    0.0000 C   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
    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
    5.7158   -1.6500    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
    5.7158   -4.1250    0.0000 O   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
    3.5724   -3.7125    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
  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 17 25  1  0  0  0  0
  8 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(CC(CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16?/m0/s1

> <INCHI_KEY>
PUETUDUXMCLALY-VYRBHSGPSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.237680509453355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.332861082666667

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.565252733196138

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.963198441804694

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6032091933503647

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
99.287

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-FEB-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-FEB-22         0                                  
HETATM    1  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   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      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   25                                                  
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                                                       
CONECT   25   24   17                                                       
CONECT   26    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(2R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

Traditional Name

(2R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

CAS Registry Number

29388-59-8

SMILES

COC1=C(O)C=CC(CC(CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16?/m0/s1

InChI Key

PUETUDUXMCLALY-VYRBHSGPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Actinidia chinensis	FooDB	PHENOL EXPLORER
Allium sativum	FooDB	PHYTOHUB
Ananas comosus	FooDB	PHENOL EXPLORER
Annona squamosa	LOTUS Database	35616633
Araucaria angustifolia	LOTUS Database	35616633
Arctium lappa	Plant	KNApSAcK
Asparagus officinalis	FooDB	PHENOL EXPLORER
Avena sativa L.	FooDB	PHENOL EXPLORER
Berberis koreana	LOTUS Database	35616633
Brassica fruticulosa	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Brassica oleracea var. gemmifera	FooDB	PHYTOHUB
Brassica oleracea var. italica	FooDB	PHYTOHUB
Brosimum acutifolium	LOTUS Database	35616633
Campylotropis hirtella	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capparis spinosa	FooDB	PHYTOHUB
Carissa edulis	LOTUS Database	35616633
Cedrus deodara	LOTUS Database	35616633
Citrus paradisi	FooDB	PHYTOHUB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	PHYTOHUB
Crossosoma bigelovii	LOTUS Database	35616633
Cucumis sativus L.	FooDB	PHENOL EXPLORER
Daphne feddei	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	PHYTOHUB
Enterococcus faecalis	LOTUS Database	35616633
Fagopyrum esculentum	FooDB	PHENOL EXPLORER
Fitzroya cupressoides	LOTUS Database	35616633
Forsythia intermedia	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
Glehnia littoralis	LOTUS Database	35616633
Glycine max	FooDB	PHENOL EXPLORER
Helianthus annuus L.	FooDB	PHENOL EXPLORER
Hordeum vulgare	FooDB	PHENOL EXPLORER
Hymenocallis littoralis	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Larix gmelinii var. olgensis	LOTUS Database	35616633
Laurus nobilis L.	Plant	KNApSAcK
Linum album	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocimum basilicum	FooDB	PHYTOHUB
Olea europaea	FooDB	PHENOL EXPLORER
Origanum vulgare	FooDB	PHYTOHUB
Papaver	FooDB	PHENOL EXPLORER
Phyllanthus angkorensis	LOTUS Database	35616633
Phyllanthus oxyphyllus	LOTUS Database	35616633
Phyllanthus polyphyllus	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Prunus armeniaca	FooDB	PHYTOHUB
Prunus persica	LOTUS Database	35616633
Randia dumetorum	LOTUS Database	35616633
Raphanus sativus var. sativus	FooDB	PHENOL EXPLORER
Ribes uva-crispa	LOTUS Database	35616633
Rosa	FooDB	PHYTOHUB
Rubia yunnanensis	LOTUS Database	35616633
Santalum album	LOTUS Database	35616633
Sargentodoxa cuneata	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Secale cereale	FooDB	PHENOL EXPLORER
Sedum sarmentosum	LOTUS Database	35616633
Sesamum indicum	FooDB	PHENOL EXPLORER
Solanum lycopersicum var. lycopersicum	FooDB	PHENOL EXPLORER
Solanum melongena	FooDB	PHENOL EXPLORER
Stereospermum colais	LOTUS Database	35616633
Taxus baccata	LOTUS Database	35616633
Taxus wallichiana	LOTUS Database	35616633
Thuja plicata	Plant	KNApSAcK
Tinospora crispa	LOTUS Database	35616633
Triticum aestivum	FooDB	PHENOL EXPLORER
Tsuga heterophylla	LOTUS Database	35616633
Urtica dioica	LOTUS Database	35616633
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitex trifolia	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Zingiber officinale	FooDB	PHYTOHUB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol lignans

Alternative Parents

Substituents

Dibenzylbutanediol
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	2.05	ALOGPS
logP	2.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	99.29 m³·mol⁻¹	ChemAxon
Polarizability	39.24 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

13391411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr. 2005 Mar;93(3):393-402. doi: 10.1079/bjn20051371. [PubMed:15877880 ]
Parikh M, Netticadan T, Pierce GN: Flaxseed: its bioactive components and their cardiovascular benefits. Am J Physiol Heart Circ Physiol. 2018 Feb 1;314(2):H146-H159. doi: 10.1152/ajpheart.00400.2017. Epub 2017 Nov 3. [PubMed:29101172 ]

Showing NP-Card for Secoisolariciresinol (NP0044237)

MOL for NP0044237 (Secoisolariciresinol)

3D MOL for NP0044237 (Secoisolariciresinol)

3D SDF for NP0044237 (Secoisolariciresinol)

3D-SDF for NP0044237 (Secoisolariciresinol)

PDB for NP0044237 (Secoisolariciresinol)

3D PDB for NP0044237 (Secoisolariciresinol)

SMILES for NP0044237 (Secoisolariciresinol)

INCHI for NP0044237 (Secoisolariciresinol)

Structure for NP0044237 (Secoisolariciresinol)

3D Structure for NP0044237 (Secoisolariciresinol)