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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 20:42:38 UTC

Update Date

2022-03-07 02:54:36 UTC

HMDB ID

HMDB0035698

Secondary Accession Numbers

HMDB0035789
HMDB35698
HMDB35789

Metabolite Identification

Common Name

Matairesinol

Description

Matairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).

Structure

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


  Mrv1652309272007272D          

 26 28  0  0  0  0            999 V2000
10001.1293 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.557510000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.706410001.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985710000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8698 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.442010000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.155910001.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.014210000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5629 9999.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.011010000.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3436 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5985 9998.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4235 9998.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6784 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.441910000.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4419 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.558310000.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9999.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5582 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13  1  1  6  0  0  0
 12  5  1  1  0  0  0
 11  9  2  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  2  1  0  0  0  0
 21  4  1  0  0  0  0
  5 19  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
M  END

HMDB0035698
     RDKit          3D
Matairesinol
 48 50  0  0  0  0  0  0  0  0999 V2000
    6.1749   -1.5116   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1464   -0.1643   -0.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866    0.5409    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8465   -0.0151    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    0.7488    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.1431    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.3264   -0.2357 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2958   -0.3271   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.3465   -2.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -0.5844   -1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756   -0.9187   -2.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685   -0.3807   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6538    0.4435    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -0.2132    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.1292    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508   -1.7699    1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3837   -1.5207    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5935   -2.1660    1.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2190   -0.6090   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2865   -0.3791   -0.9189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2550    0.5188   -1.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0107    0.0377   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.0725    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.6468    0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2995    1.8937    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738    2.4376    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056   -1.6533   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1679   -1.9126   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3502   -2.0658   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -1.0742    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.7404    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -0.9131    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    1.3930   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5310   -1.3681   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    0.2235   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -1.3935    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6979    1.4692    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    0.5404    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.3788    2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -2.4969    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8046   -2.8380    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8913    0.0667   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2841    0.9087   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6425    1.4051   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.7613   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    2.7113    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    3.7084    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7529    3.3920    0.3266 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12  7  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  6
  8 34  1  0
  8 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
M  END


  Mrv1652309272007272D          

 26 28  0  0  0  0            999 V2000
10001.1293 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.557510000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.706410001.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985710000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8698 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.442010000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.155910001.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.014210000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5629 9999.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.011010000.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3436 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5985 9998.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4235 9998.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6784 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.441910000.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4419 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.558310000.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9999.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5582 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13  1  1  6  0  0  0
 12  5  1  1  0  0  0
 11  9  2  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  2  1  0  0  0  0
 21  4  1  0  0  0  0
  5 19  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035698

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

> <INCHI_KEY>
MATGKVZWFZHCLI-LSDHHAIUSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.3851

> <EXACT_MASS>
358.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.8600588964603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.2917825110000005

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.246760875760991

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.644700805894656

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5896887507776425

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
95.6344

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
matairesinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035698
     RDKit          3D
Matairesinol
 48 50  0  0  0  0  0  0  0  0999 V2000
    6.1749   -1.5116   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1464   -0.1643   -0.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866    0.5409    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8465   -0.0151    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    0.7488    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.1431    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.3264   -0.2357 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2958   -0.3271   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.3465   -2.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -0.5844   -1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756   -0.9187   -2.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685   -0.3807   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6538    0.4435    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -0.2132    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.1292    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508   -1.7699    1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3837   -1.5207    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5935   -2.1660    1.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2190   -0.6090   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2865   -0.3791   -0.9189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2550    0.5188   -1.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0107    0.0377   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.0725    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.6468    0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2995    1.8937    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738    2.4376    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056   -1.6533   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1679   -1.9126   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3502   -2.0658   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -1.0742    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.7404    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -0.9131    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    1.3930   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5310   -1.3681   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    0.2235   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -1.3935    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6979    1.4692    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    0.5404    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.3788    2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -2.4969    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8046   -2.8380    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8913    0.0667   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2841    0.9087   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6425    1.4051   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.7613   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    2.7113    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    3.7084    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7529    3.3920    0.3266 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12  7  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  6
  8 34  1  0
  8 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  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    8668.7758663.891   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.4418668.508   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.8528669.423   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8674.1078666.969   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8664.5578663.891   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8661.8928668.508   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.2248669.273   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8659.2278666.969   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8663.9848666.576   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8666.6878667.022   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8665.4418666.116   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9178664.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.4578664.652   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.9338666.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.8928666.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.5588666.199   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.5588664.659   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.8928663.889   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.2258664.659   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8663.2258666.199   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7768666.199   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.4428666.969   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.1088666.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.1088664.659   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.4428663.889   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.7768664.659   0.000  0.00  0.00           C+0
CONECT    1   13   24                                                       
CONECT    2    3   22                                                       
CONECT    3    2                                                            
CONECT    4   21                                                            
CONECT    5   12   19                                                       
CONECT    6    7   15                                                       
CONECT    7    6                                                            
CONECT    8   16                                                            
CONECT    9   11                                                            
CONECT   10   11   14                                                       
CONECT   11   12   10    9                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12   14    1                                                  
CONECT   14   13   10                                                       
CONECT   15   16   20    6                                                  
CONECT   16   15   17    8                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    5                                                  
CONECT   20   19   15                                                       
CONECT   21   22   26    4                                                  
CONECT   22   21   23    2                                                  
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   56    0
END

COMPND    HMDB0035698
HETATM    1  C1  UNL     1       6.175  -1.512  -0.824  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.146  -0.164  -0.455  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.087   0.541   0.051  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.847  -0.015   0.270  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.821   0.749   0.783  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.481   0.143   1.017  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.677   0.326  -0.236  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.296  -0.327  -1.439  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.164  -0.346  -2.331  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.977  -0.584  -1.588  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.076  -0.919  -2.083  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.668  -0.381  -0.171  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.654   0.444   0.605  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.957  -0.213   0.679  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.149  -1.129   1.695  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.351  -1.770   1.828  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.384  -1.521   0.964  1.00  0.00           C  
HETATM   18  O4  UNL     1      -6.594  -2.166   1.098  1.00  0.00           O  
HETATM   19  C15 UNL     1      -5.219  -0.609  -0.060  1.00  0.00           C  
HETATM   20  O5  UNL     1      -6.286  -0.379  -0.919  1.00  0.00           O  
HETATM   21  C16 UNL     1      -6.255   0.519  -1.997  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.011   0.038  -0.197  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.039   2.072   1.077  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.273   2.647   0.865  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.299   1.894   0.354  1.00  0.00           C  
HETATM   26  O6  UNL     1       6.574   2.438   0.122  1.00  0.00           O  
HETATM   27  H1  UNL     1       6.206  -1.653  -1.930  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.168  -1.913  -0.446  1.00  0.00           H  
HETATM   29  H3  UNL     1       5.350  -2.066  -0.350  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.653  -1.074   0.038  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.996   0.740   1.816  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.556  -0.913   1.305  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.463   1.393  -0.418  1.00  0.00           H  
HETATM   34  H8  UNL     1       1.531  -1.368  -1.173  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.132   0.224  -1.871  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.526  -1.394   0.287  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.698   1.469   0.181  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.244   0.540   1.634  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.375  -1.379   2.418  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.489  -2.497   2.641  1.00  0.00           H  
HETATM   41  H15 UNL     1      -6.805  -2.838   1.804  1.00  0.00           H  
HETATM   42  H16 UNL     1      -5.891   0.067  -2.940  1.00  0.00           H  
HETATM   43  H17 UNL     1      -7.284   0.909  -2.146  1.00  0.00           H  
HETATM   44  H18 UNL     1      -5.643   1.405  -1.725  1.00  0.00           H  
HETATM   45  H19 UNL     1      -3.862   0.761  -0.981  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.264   2.711   1.482  1.00  0.00           H  
HETATM   47  H21 UNL     1       4.447   3.708   1.100  1.00  0.00           H  
HETATM   48  H22 UNL     1       6.753   3.392   0.327  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   12   33
CONECT    8    9   34   35
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   36
CONECT   13   14   37   38
CONECT   14   15   15   22
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   19
CONECT   18   41
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   42   43   44
CONECT   22   45
CONECT   23   24   46
CONECT   24   25   25   47
CONECT   25   26
CONECT   26   48
END

HMDB0035698
     RDKit          3D
Matairesinol
 48 50  0  0  0  0  0  0  0  0999 V2000
    6.1749   -1.5116   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1464   -0.1643   -0.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866    0.5409    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8465   -0.0151    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    0.7488    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812    0.1431    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.3264   -0.2357 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2958   -0.3271   -1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -0.3465   -2.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -0.5844   -1.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0756   -0.9187   -2.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685   -0.3807   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6538    0.4435    0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -0.2132    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -1.1292    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508   -1.7699    1.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3837   -1.5207    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5935   -2.1660    1.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2190   -0.6090   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2865   -0.3791   -0.9189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2550    0.5188   -1.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0107    0.0377   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.0725    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2725    2.6468    0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2995    1.8937    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5738    2.4376    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056   -1.6533   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1679   -1.9126   -0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3502   -2.0658   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -1.0742    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957    0.7404    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -0.9131    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    1.3930   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5310   -1.3681   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    0.2235   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -1.3935    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6979    1.4692    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444    0.5404    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.3788    2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -2.4969    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8046   -2.8380    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8913    0.0667   -2.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2841    0.9087   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6425    1.4051   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620    0.7613   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642    2.7113    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    3.7084    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7529    3.3920    0.3266 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12  7  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  6
  8 34  1  0
  8 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone	ChEBI
Artigenin congener	ChEBI
(-)-Matairesinol	Kegg
(3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one	Kegg
(8R,8'r)-(-)-Matairesinol	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone	HMDB
Matai-resinol	HMDB
(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone	HMDB
(8R,8’R)-(-)-matairesinol	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone	HMDB
Dihydro-3,4-divanillyl-2(3H)-furanone	HMDB
Matairesinol	ChEBI

Chemical Formula

C₂₀H₂₂O₆

Average Molecular Weight

358.3851

Monoisotopic Molecular Weight

358.141638436

IUPAC Name

(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

matairesinol

CAS Registry Number

580-72-3

SMILES

COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

InChI Key

MATGKVZWFZHCLI-LSDHHAIUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

polyphenol (CHEBI:6698 )
gamma-lactone (CHEBI:6698 )
lignan (CHEBI:6698 )
Lignans (C10682 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0035698)
Cell membrane (HMDB: HMDB0035698)

Excreta

Biofluid or Excreta

Urine (PMID: 8017326)

Source

Exogenous

Exogenous (HMDB: HMDB0035698)

Food

Food (HMDB: HMDB0035698)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)
Sesame (FooDB: FOOD00170)

Spice

Capers (FooDB: FOOD00039)

Cereal and cereal product

Leavened bread

Rye bread (FooDB: FOOD00809)

Cereal

Rye (FooDB: FOOD00169)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035698)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 °C	Not Available
Boiling Point	593.03 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	50.71 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.655 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	2.79	ALOGPS
logP	3.29	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.63 m³·mol⁻¹	ChemAxon
Polarizability	36.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.362	31661259
DarkChem	[M-H]-	186.941	31661259
DeepCCS	[M+H]+	188.025	30932474
DeepCCS	[M-H]-	185.629	30932474
DeepCCS	[M-2H]-	218.803	30932474
DeepCCS	[M+Na]+	194.049	30932474
AllCCS	[M+H]+	186.7	32859911
AllCCS	[M+H-H2O]+	183.5	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.5	32859911
AllCCS	[M-H]-	189.0	32859911
AllCCS	[M+Na-2H]-	189.1	32859911
AllCCS	[M+HCOO]-	189.3	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.	6.26 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5787 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2201.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	232.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	648.0 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	490.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1218.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	516.0 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	1283.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	171.5 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	60.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Matairesinol	COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1	5024.8	Standard polar	33892256
Matairesinol	COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1	3124.7	Standard non polar	33892256
Matairesinol	COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1	3192.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Matairesinol,1TMS,isomer #1	COC1=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3180.4	Semi standard non polar	33892256
Matairesinol,1TMS,isomer #2	COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	3181.7	Semi standard non polar	33892256
Matairesinol,2TMS,isomer #1	COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	3200.7	Semi standard non polar	33892256
Matairesinol,1TBDMS,isomer #1	COC1=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3442.6	Semi standard non polar	33892256
Matairesinol,1TBDMS,isomer #2	COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	3443.4	Semi standard non polar	33892256
Matairesinol,2TBDMS,isomer #1	COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3687.0	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 - Matairesinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0912000000-7b4af0e03073d528f059	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matairesinol GC-MS (2 TMS) - 70eV, Positive	splash10-052o-1050900000-0801cdc5bc6f2e25f382	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Matairesinol 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 - Matairesinol 6V, Positive-QTOF	splash10-000i-1910000000-191002f29f51f8e6746e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-0079-1900000000-ad747afeebed0450284c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-000i-0910000000-d73fdf135ee1bbb9da5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-000i-0910000000-13d87e9eff437c2a9d40	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-000i-0915000000-b1d73d4f3f39292146a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 30V, Positive-QTOF	splash10-000i-0900000000-09f594bc50d3bf31b0a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-0a4l-0009000000-6831b867bff98cf45ad0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-000i-0915000000-057c5e3fa08e00ed5af0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 50V, Positive-QTOF	splash10-000i-1900000000-9c62c902e5e1ba7ce812	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-0a4l-0109000000-659f3b6afcb8605169af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 50V, Positive-QTOF	splash10-000i-1910000000-28e93dc2781ea1307a60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 30V, Positive-QTOF	splash10-000i-0910000000-bd8df1e0e46ee7a489b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-0a4l-0009000000-fd38fb0f0d7d7af381a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-000i-0915000000-854075d816aefffb1afb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-000i-0915000000-b52be1df53fd1d7baa01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-000i-1900000000-6a7fe76ee0a12b4bfac3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOF	splash10-000i-0915000000-78d9cef4ae13070206f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 40V, Negative-QTOF	splash10-00di-0910000000-f8a176428857ea61be78	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Matairesinol 20V, Negative-QTOF	splash10-0abi-0948000000-33391728008094755667	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOF	splash10-0a4i-0229000000-da790a5b3ff80ab843dc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 20V, Positive-QTOF	splash10-06ri-0978000000-407d81dd6dfadba216c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 40V, Positive-QTOF	splash10-0ims-1910000000-060bdfec7823f760bd09	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 10V, Negative-QTOF	splash10-0a4i-0009000000-25c656431001e8e5785f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 20V, Negative-QTOF	splash10-0bt9-0129000000-eefe04935cde889de64c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Matairesinol 40V, Negative-QTOF	splash10-01ot-0986000000-2b1737e1ecb9a7ee39f9	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
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
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 595	8017326	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 595	10798213	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 595	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 595	7722188	details
Urine	Detected and Quantified	0.00467 +/- 0.00933 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.00400 +/- 0.00333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.0653 +/- 0.00867 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	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

DB04200

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Matairesinol

METLIN ID

Not Available

PubChem Compound

119205

PDB ID

Not Available

ChEBI ID

6698

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800. [PubMed:18803219 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Matairesinol (HMDB0035698)

MOL for HMDB0035698 (Matairesinol)

3D MOL for HMDB0035698 (Matairesinol)

3D SDF for HMDB0035698 (Matairesinol)

3D-SDF for HMDB0035698 (Matairesinol)

PDB for HMDB0035698 (Matairesinol)

3D PDB for HMDB0035698 (Matairesinol)

SMILES for HMDB0035698 (Matairesinol)

INCHI for HMDB0035698 (Matairesinol)

Structure for HMDB0035698 (Matairesinol)

3D Structure for HMDB0035698 (Matairesinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra