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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-04-03 14:10:33 UTC

Update Date

2021-09-14 14:57:21 UTC

HMDB ID

HMDB0013692

Secondary Accession Numbers

HMDB13692

Metabolite Identification

Common Name

Secoisolariciresinol

Description

Secoisolariciresinol, also known as knotolan, belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol has been detected, but not quantified in, several different foods, such as cocoa beans (Theobroma cacao), swiss chards (Beta vulgaris ssp. cicla), tartary buckwheats (Fagopyrum tataricum), chanterelles (Cantharellus cibarius), and kohlrabis (Brassica oleracea var. gongylodes). This could make secoisolariciresinol a potential biomarker for the consumption of these foods. Secoisolariciresinol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Secoisolariciresinol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007362D          

 26 27  0  0  0  0            999 V2000
10001.807510000.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.091810000.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.377910000.4943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.663410000.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2326 9998.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9470 9998.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8059 9999.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3779 9999.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6634 9999.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.091810001.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.807510002.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.236710002.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.384910003.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.663810002.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.233910000.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.519510000.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5195 9999.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2339 9999.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9485 9999.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.948510000.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950610001.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.236110002.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.521410001.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.521410000.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235910000.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950610000.9055    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
  2 10  1  6  0  0  0
  3  4  1  0  0  0  0
  3  8  1  6  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 20 15  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
  1 24  1  0  0  0  0
 22 12  1  0  0  0  0
 21 14  1  0  0  0  0
  4 20  1  0  0  0  0
 18  5  1  0  0  0  0
 17  7  1  0  0  0  0
M  END

HMDB0013692
     RDKit          3D
Secoisolariciresinol
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.1579    0.3706   -3.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248    1.2563   -2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3298    1.0842   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339    0.1135   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.0926    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1125    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8386    1.6349 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4049    0.2803    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000    1.4955    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211   -1.0182    0.6483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4491   -0.2741   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -0.4747   -1.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099   -0.8754    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9158   -1.0638    0.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427   -2.3192    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4943   -2.4081   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0490   -1.3088   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042   -1.4486   -2.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139   -0.0615   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492    1.0620   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936    2.3341   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    0.0429   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.7706    1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.7410    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422    1.9112    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600    2.9230   -0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433   -0.7014   -2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.5289   -3.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.5195   -4.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0939   -0.5355   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -2.0286    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -1.5698    2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -1.7594    2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    0.2609    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.0019    3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.5701    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -2.1346    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.6106   -1.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774    0.8175   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -1.3151   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.1955    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.5229    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -3.1368    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8909   -3.4083   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4899   -2.3598   -2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    2.4928   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1424    3.1129   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585    2.3782   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455    1.0454   -0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.6447    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782    2.4164    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    3.0128   -1.0645 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  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 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
M  END


  Mrv1652309272007362D          

 26 27  0  0  0  0            999 V2000
10001.807510000.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.091810000.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.377910000.4943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.663410000.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2326 9998.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9470 9998.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8059 9999.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3779 9999.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6634 9999.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.091810001.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.807510002.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.236710002.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.384910003.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.663810002.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.233910000.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.519510000.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5195 9999.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2339 9999.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9485 9999.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.948510000.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950610001.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.236110002.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.521410001.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.521410000.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235910000.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.950610000.9055    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
  2 10  1  6  0  0  0
  3  4  1  0  0  0  0
  3  8  1  6  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 20 15  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
  1 24  1  0  0  0  0
 22 12  1  0  0  0  0
 21 14  1  0  0  0  0
  4 20  1  0  0  0  0
 18  5  1  0  0  0  0
 17  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013692

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(C[C@@H](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-HOTGVXAUSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.4168

> <EXACT_MASS>
362.172938564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.593055680652554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-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>
99.28699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
secoisolariciresinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013692
     RDKit          3D
Secoisolariciresinol
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.1579    0.3706   -3.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248    1.2563   -2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3298    1.0842   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339    0.1135   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.0926    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1125    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8386    1.6349 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4049    0.2803    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000    1.4955    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211   -1.0182    0.6483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4491   -0.2741   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -0.4747   -1.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099   -0.8754    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9158   -1.0638    0.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427   -2.3192    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4943   -2.4081   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0490   -1.3088   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042   -1.4486   -2.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139   -0.0615   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492    1.0620   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936    2.3341   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    0.0429   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.7706    1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.7410    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422    1.9112    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600    2.9230   -0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433   -0.7014   -2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.5289   -3.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.5195   -4.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0939   -0.5355   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -2.0286    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -1.5698    2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -1.7594    2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    0.2609    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.0019    3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.5701    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -2.1346    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.6106   -1.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774    0.8175   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -1.3151   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.1955    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.5229    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -3.1368    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8909   -3.4083   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4899   -2.3598   -2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    2.4928   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1424    3.1129   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585    2.3782   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455    1.0454   -0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.6447    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782    2.4164    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    3.0128   -1.0645 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  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 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8670.0418667.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.7058668.356   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.3728667.589   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.0388668.356   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8663.3688663.738   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8664.7018662.970   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8660.7048665.278   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8667.3728666.050   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8666.0388665.278   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8668.7058669.896   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8670.0418670.670   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8672.7098672.210   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8671.1198673.126   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8675.3728670.670   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8663.3708668.359   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.0368667.589   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0368666.048   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3708665.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.7048666.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.7048667.589   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8674.0418669.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7078670.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.3738669.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.3738668.357   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8672.7078667.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8674.0418668.357   0.000  0.00  0.00           C+0
CONECT    1    2   24                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3   20                                                       
CONECT    5    6   18                                                       
CONECT    6    5                                                            
CONECT    7   17                                                            
CONECT    8    3    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11                                                       
CONECT   11   10                                                            
CONECT   12   13   22                                                       
CONECT   13   12                                                            
CONECT   14   21                                                            
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    7                                                  
CONECT   18   17   19    5                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15    4                                                  
CONECT   21   22   26   14                                                  
CONECT   22   21   23   12                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25    1                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0013692
HETATM    1  C1  UNL     1       4.158   0.371  -3.001  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.725   1.256  -2.053  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.330   1.084  -0.732  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.434   0.114  -0.320  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.016  -0.093   0.958  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.061  -1.113   1.396  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.655  -0.839   1.635  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.405   0.280   2.657  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.900   1.496   2.263  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.421  -1.018   0.648  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.449  -0.274  -0.631  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.595  -0.475  -1.507  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.810  -0.875   1.260  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.916  -1.064   0.333  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.443  -2.319   0.081  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.494  -2.408  -0.794  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.049  -1.309  -1.431  1.00  0.00           C  
HETATM   18  O4  UNL     1      -6.104  -1.449  -2.301  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.514  -0.061  -1.171  1.00  0.00           C  
HETATM   20  O5  UNL     1      -5.049   1.062  -1.795  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.494   2.334  -1.521  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.455   0.043  -0.292  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.563   0.771   1.926  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.451   1.741   1.554  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.842   1.911   0.243  1.00  0.00           C  
HETATM   26  O6  UNL     1       5.760   2.923  -0.106  1.00  0.00           O  
HETATM   27  H1  UNL     1       4.343  -0.701  -2.733  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.063   0.529  -3.081  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.582   0.520  -4.015  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.094  -0.536  -1.129  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.165  -2.029   0.698  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.568  -1.570   2.330  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.377  -1.759   2.387  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.618   0.261   3.042  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.021  -0.002   3.562  1.00  0.00           H  
HETATM   36  H10 UNL     1       0.831   1.570   1.296  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.407  -2.135   0.314  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.360  -0.611  -1.241  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.677   0.818  -0.497  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.472  -1.315  -1.997  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.890   0.196   1.613  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.974  -1.523   2.134  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.977  -3.137   0.600  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.891  -3.408  -0.975  1.00  0.00           H  
HETATM   45  H19 UNL     1      -6.490  -2.360  -2.487  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.466   2.493  -0.413  1.00  0.00           H  
HETATM   47  H21 UNL     1      -5.142   3.113  -1.982  1.00  0.00           H  
HETATM   48  H22 UNL     1      -3.459   2.378  -1.893  1.00  0.00           H  
HETATM   49  H23 UNL     1      -3.045   1.045  -0.100  1.00  0.00           H  
HETATM   50  H24 UNL     1       3.290   0.645   2.970  1.00  0.00           H  
HETATM   51  H25 UNL     1       4.878   2.416   2.311  1.00  0.00           H  
HETATM   52  H26 UNL     1       6.017   3.013  -1.064  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   30
CONECT    5    6   23   23
CONECT    6    7   31   32
CONECT    7    8   10   33
CONECT    8    9   34   35
CONECT    9   36
CONECT   10   11   13   37
CONECT   11   12   38   39
CONECT   12   40
CONECT   13   14   41   42
CONECT   14   15   15   22
CONECT   15   16   43
CONECT   16   17   17   44
CONECT   17   18   19
CONECT   18   45
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   46   47   48
CONECT   22   49
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   26
CONECT   26   52
END

HMDB0013692
     RDKit          3D
Secoisolariciresinol
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.1579    0.3706   -3.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248    1.2563   -2.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3298    1.0842   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339    0.1135   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.0926    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -1.1125    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8386    1.6349 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4049    0.2803    2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000    1.4955    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4211   -1.0182    0.6483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4491   -0.2741   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -0.4747   -1.5066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099   -0.8754    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9158   -1.0638    0.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4427   -2.3192    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4943   -2.4081   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0490   -1.3088   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042   -1.4486   -2.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139   -0.0615   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492    1.0620   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936    2.3341   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550    0.0429   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.7706    1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515    1.7410    1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422    1.9112    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600    2.9230   -0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433   -0.7014   -2.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.5289   -3.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    0.5195   -4.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0939   -0.5355   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646   -2.0286    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684   -1.5698    2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -1.7594    2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    0.2609    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.0019    3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    1.5701    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -2.1346    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.6106   -1.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774    0.8175   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -1.3151   -1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    0.1955    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -1.5229    2.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767   -3.1368    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8909   -3.4083   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4899   -2.3598   -2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    2.4928   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1424    3.1129   -1.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585    2.3782   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455    1.0454   -0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895    0.6447    2.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8782    2.4164    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    3.0128   -1.0645 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  1  0
  7  8  1  0
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  7 10  1  0
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 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
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 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Secoisolariciresinol	Kegg
2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediol	MeSH
Knotolan	MeSH
Secoisolariciresinol, (r,s)-isomer	MeSH
Secoisolariciresinol	ChEBI
(8R,8'R)-(-)-Secoisolariciresinol	PhytoBank
(8R,8’R)-(-)-Secoisolariciresinol	PhytoBank
seco-Isolariciresinol	PhytoBank
2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol	PhytoBank
2,3-Divanillyl-1,4-butanediol	PhytoBank

Chemical Formula

C₂₀H₂₆O₆

Average Molecular Weight

362.4168

Monoisotopic Molecular Weight

362.172938564

IUPAC Name

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

Traditional Name

secoisolariciresinol

CAS Registry Number

29388-59-8

SMILES

COC1=C(O)C=CC(C[C@@H](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-HOTGVXAUSA-N

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
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secoisolariciresinol (CHEBI:65004 )
Lignans (C18167 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 17353586)
Feces (PMID: 29808030)

Cellular substructure

Membrane (HMDB: HMDB0013692)

Source

Exogenous

Exogenous (HMDB: HMDB0013692)

Food

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Citrus

Grapefruit (FooDB: FOOD00256)
Sweet orange (FooDB: FOOD00057)

Tropical fruit

Kiwi (FooDB: FOOD00004)
Pineapple (FooDB: FOOD00012)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit vegetable

Cabbage

Broccoli (FooDB: FOOD00034)
Brussel sprouts (FooDB: FOOD00032)

Root vegetable

Carrot (FooDB: FOOD00245)
Radish (var.) (FooDB: FOOD00263)

Cereal and cereal product

Leavened bread

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Pulse

Bean

Mung bean (FooDB: FOOD00200)
Broad bean (FooDB: FOOD00197)

Pea

Black-eyed pea (FooDB: FOOD00523)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Milk and milk product

Fermented milk product

Yogurt (FooDB: FOOD00620)

Gourd

Cucumber (FooDB: FOOD00065)

Herb and spice

Herb

Spice

Ginger (FooDB: FOOD00206)
Capers (FooDB: FOOD00039)

Oilseed crop

Flaxseed (FooDB: FOOD00101)
Sesame (FooDB: FOOD00170)
Poppy (FooDB: FOOD00127)
Sunflower (FooDB: FOOD00086)

Tea

Tea (FooDB: FOOD00038)
Black tea (FooDB: FOOD00907)
Green tea (FooDB: FOOD00908)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Endogenous

Endogenous (HMDB: HMDB0013692)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0013692)
Antioxidant (HMDB: HMDB0013692)

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0013692)

Biological role

Modulator

Inhibitor

EC 1.14.14.14 (aromatase) inhibitor (HMDB: HMDB0013692)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
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	38.59 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.409	31661259
DarkChem	[M-H]-	180.706	31661259
DeepCCS	[M+H]+	189.996	30932474
DeepCCS	[M-H]-	187.638	30932474
DeepCCS	[M-2H]-	220.911	30932474
DeepCCS	[M+Na]+	196.14	30932474
AllCCS	[M+H]+	188.2	32859911
AllCCS	[M+H-H2O]+	185.1	32859911
AllCCS	[M+NH4]+	191.0	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	189.6	32859911
AllCCS	[M+Na-2H]-	190.2	32859911
AllCCS	[M+HCOO]-	191.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.08 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0499 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	42.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1707.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	188.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	472.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	360.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	870.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	426.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1061.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	282.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	276.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Secoisolariciresinol	COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1	4946.0	Standard polar	33892256
Secoisolariciresinol	COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1	3234.4	Standard non polar	33892256
Secoisolariciresinol	COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1	3271.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Secoisolariciresinol,1TMS,isomer #1	COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3142.6	Semi standard non polar	33892256
Secoisolariciresinol,1TMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O	3098.7	Semi standard non polar	33892256
Secoisolariciresinol,2TMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3027.1	Semi standard non polar	33892256
Secoisolariciresinol,2TMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3026.0	Semi standard non polar	33892256
Secoisolariciresinol,2TMS,isomer #3	COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	3080.0	Semi standard non polar	33892256
Secoisolariciresinol,2TMS,isomer #4	COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O	3033.5	Semi standard non polar	33892256
Secoisolariciresinol,3TMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	2968.8	Semi standard non polar	33892256
Secoisolariciresinol,3TMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	3006.6	Semi standard non polar	33892256
Secoisolariciresinol,4TMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C)[C@H](CO[Si](C)(C)C)CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	2997.1	Semi standard non polar	33892256
Secoisolariciresinol,1TBDMS,isomer #1	COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3420.3	Semi standard non polar	33892256
Secoisolariciresinol,1TBDMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O	3381.2	Semi standard non polar	33892256
Secoisolariciresinol,2TBDMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3564.3	Semi standard non polar	33892256
Secoisolariciresinol,2TBDMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3564.4	Semi standard non polar	33892256
Secoisolariciresinol,2TBDMS,isomer #3	COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3624.1	Semi standard non polar	33892256
Secoisolariciresinol,2TBDMS,isomer #4	COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O	3577.3	Semi standard non polar	33892256
Secoisolariciresinol,3TBDMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3738.7	Semi standard non polar	33892256
Secoisolariciresinol,3TBDMS,isomer #2	COC1=CC(C[C@@H](CO)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3746.4	Semi standard non polar	33892256
Secoisolariciresinol,4TBDMS,isomer #1	COC1=CC(C[C@@H](CO[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3901.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-0905000000-3c10a7ce80aa82270fdf	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Secoisolariciresinol GC-MS (4 TMS) - 70eV, Positive	splash10-000i-7222129000-4a15ee9d5480cd864709	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Secoisolariciresinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol LC-ESI-qTof , Positive-QTOF	splash10-000i-0931000000-1875abcf0a77c29ef991	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol , positive-QTOF	splash10-000i-0931000000-1875abcf0a77c29ef991	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOF	splash10-0079-1900000000-388f0c7eb9705dc8b6bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOF	splash10-000i-0910000000-260d238ae45a244f9000	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-000i-0923000000-8b6573966f9f0d0dc18e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOF	splash10-000i-0900000000-1c5c1767a5d18a1ce39b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-000i-0923000000-d1247d61323b3bb185a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOF	splash10-0079-1900000000-0dd02f8018fd55488472	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 50V, Positive-QTOF	splash10-010c-2900000000-36ffcea5d0b4db42ec25	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-000i-0921000000-428dc5bb31028e4394cf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 30V, Positive-QTOF	splash10-000i-0900000000-7060ec03d70103514c76	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-004i-0429000000-83bec5092dea63cd01c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 35V, Negative-QTOF	splash10-03di-0009000000-87492c20c18d06242b0a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Secoisolariciresinol 6V, Positive-QTOF	splash10-0079-1900000000-f8cde078d6625c8f94eb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-03dj-0119000000-3af20da7d20bab27dd05	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Positive-QTOF	splash10-01tj-0749000000-cfac94ec5340c6222037	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Positive-QTOF	splash10-0a4r-0894000000-598931011d02757fdeba	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Negative-QTOF	splash10-03di-0009000000-bb339709d3dc1a17e110	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Negative-QTOF	splash10-03di-0009000000-bd59bd756314c4c5af52	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Negative-QTOF	splash10-014i-0349000000-ab9158c58cc922e633dd	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Negative-QTOF	splash10-03di-0009000000-55f1e5434dd9fb2f906e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Negative-QTOF	splash10-02t9-0009000000-7e6fdc2276121d8b599c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 40V, Negative-QTOF	splash10-0aor-0459000000-a7a975e7dbb9db40e2b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 10V, Positive-QTOF	splash10-03di-0229000000-7b1b915316723c3b027a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Secoisolariciresinol 20V, Positive-QTOF	splash10-0ads-0869000000-e600d806308ccec4045c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.0400 +/- 0.0933 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12179

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Secoisolariciresinol

METLIN ID

Not Available

PubChem Compound

65373

PDB ID

Not Available

ChEBI ID

65004

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Abarzua S, Serikawa T, Szewczyk M, Richter DU, Piechulla B, Briese V: Antiproliferative activity of lignans against the breast carcinoma cell lines MCF 7 and BT 20. Arch Gynecol Obstet. 2012 Apr;285(4):1145-51. doi: 10.1007/s00404-011-2120-6. Epub 2011 Oct 30. [PubMed:22037685 ]

Showing metabocard for Secoisolariciresinol (HMDB0013692)

MOL for HMDB0013692 (Secoisolariciresinol)

3D MOL for HMDB0013692 (Secoisolariciresinol)

3D SDF for HMDB0013692 (Secoisolariciresinol)

3D-SDF for HMDB0013692 (Secoisolariciresinol)

PDB for HMDB0013692 (Secoisolariciresinol)

3D PDB for HMDB0013692 (Secoisolariciresinol)

SMILES for HMDB0013692 (Secoisolariciresinol)

INCHI for HMDB0013692 (Secoisolariciresinol)

Structure for HMDB0013692 (Secoisolariciresinol)

3D Structure for HMDB0013692 (Secoisolariciresinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra