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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:16:35 UTC

Update Date

2022-03-07 02:55:59 UTC

HMDB ID

HMDB0038928

Secondary Accession Numbers

HMDB38928

Metabolite Identification

Common Name

Lirioresinol A

Description

Lirioresinol A, also known as S(8-8)S, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Lirioresinol A has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make lirioresinol a a potential biomarker for the consumption of these foods. Lirioresinol A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Lirioresinol A.

Structure

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


  Mrv1652309271714262D          

 30 33  0  0  0  0            999 V2000
    0.3392    3.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    2.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547    0.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236    1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4848   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5272   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END

HMDB0038928
     RDKit          3D
Lirioresinol A
 56 59  0  0  0  0  0  0  0  0999 V2000
   -6.0382   -2.9185   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533   -1.6538   -0.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.7126    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0308   -1.0024   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.0474   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.3326   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.5481   -0.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -1.4933   -0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -0.1347   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    0.5732    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9798    0.1667    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905   -0.9697    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8337   -1.3441    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -2.5105    1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513   -3.2901    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7047   -0.5504   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.9472   -0.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    0.5970   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.3518   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8477    2.5397   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892    0.9499   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    0.4863    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    0.6845    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    0.6443   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712    1.1852    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6693    1.4786    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    2.7173    1.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    3.6866    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6718    0.5200    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8612    0.9396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571   -3.4325    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9615   -3.5337   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908   -2.7564   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -1.9828   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.3453   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244   -2.3326   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.5230    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -0.0803   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6700   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7923   -1.5790    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623   -2.6417    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.6241    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -4.1111    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7280   -0.4202   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    2.6151   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037    3.3904   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5170    2.7057   -3.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    1.8608   -1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -0.1519    1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839    1.6703    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    1.6289   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767    1.9108    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    3.2500    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    4.0225    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508    4.5868    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7022    0.2161    0.8774 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 29  3  1  0
 24  6  1  0
 24  9  1  0
 21 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 30 56  1  0
M  END


  Mrv1652309271714262D          

 30 33  0  0  0  0            999 V2000
    0.3392    3.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5943    2.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0423    2.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547    0.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    1.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236    1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4848   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6313   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2452   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3342   -3.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891   -4.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5272   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038928

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3

> <INCHI_KEY>
KOWMJRJXZMEZLD-UHFFFAOYSA-N

> <FORMULA>
C22H26O8

> <MOLECULAR_WEIGHT>
418.437

> <EXACT_MASS>
418.162767808

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.995113664664714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
1.9624170159999994

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.60402888358133

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.001968892253409

> <JCHEM_PKA_STRONGEST_BASIC>
-3.741418411118898

> <JCHEM_POLAR_SURFACE_AREA>
95.84000000000002

> <JCHEM_REFRACTIVITY>
108.02659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
syringaresinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038928
     RDKit          3D
Lirioresinol A
 56 59  0  0  0  0  0  0  0  0999 V2000
   -6.0382   -2.9185   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533   -1.6538   -0.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.7126    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0308   -1.0024   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.0474   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.3326   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.5481   -0.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -1.4933   -0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -0.1347   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    0.5732    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9798    0.1667    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905   -0.9697    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8337   -1.3441    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -2.5105    1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513   -3.2901    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7047   -0.5504   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.9472   -0.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    0.5970   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.3518   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8477    2.5397   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892    0.9499   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    0.4863    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    0.6845    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    0.6443   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712    1.1852    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6693    1.4786    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    2.7173    1.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    3.6866    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6718    0.5200    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8612    0.9396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571   -3.4325    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9615   -3.5337   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908   -2.7564   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -1.9828   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.3453   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244   -2.3326   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.5230    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -0.0803   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6700   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7923   -1.5790    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623   -2.6417    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.6241    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -4.1111    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7280   -0.4202   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    2.6151   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037    3.3904   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5170    2.7057   -3.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    1.8608   -1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -0.1519    1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839    1.6703    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    1.6289   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767    1.9108    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    3.2500    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    4.0225    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508    4.5868    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7022    0.2161    0.8774 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 29  3  1  0
 24  6  1  0
 24  9  1  0
 21 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 30 56  1  0
M  END

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  C   UNK     0       0.633   6.683   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.109   5.218   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.079   4.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.555   2.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.475   1.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.982   1.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.458   3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.964   3.569   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.440   5.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.427   4.394   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.903   5.858   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.905  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -2.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.835  -1.246   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.912  -4.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.894  -6.061   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.924  -4.917   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.357  -6.886   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.833  -8.350   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.820  -7.710   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   20                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0038928
HETATM    1  C1  UNL     1      -6.038  -2.918  -0.631  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.353  -1.654  -0.102  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.341  -0.713   0.012  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.031  -1.002  -0.387  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.042  -0.047  -0.263  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.673  -0.333  -0.673  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.188  -1.548  -0.271  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.195  -1.493  -0.196  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.607  -0.135  -0.720  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.605   0.573   0.135  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.980   0.167   0.046  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.490  -0.970   0.635  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.834  -1.344   0.532  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.261  -2.510   1.162  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.351  -3.290   1.885  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.705  -0.550  -0.191  1.00  0.00           C  
HETATM   17  O4  UNL     1       7.032  -0.947  -0.276  1.00  0.00           O  
HETATM   18  C14 UNL     1       5.219   0.597  -0.794  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.127   1.352  -1.502  1.00  0.00           O  
HETATM   20  C15 UNL     1       5.848   2.540  -2.183  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.889   0.950  -0.680  1.00  0.00           C  
HETATM   22  O6  UNL     1       1.018   0.486   1.395  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.344   0.685   1.209  1.00  0.00           C  
HETATM   24  C18 UNL     1      -0.647   0.644  -0.253  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.371   1.185   0.257  1.00  0.00           C  
HETATM   26  C20 UNL     1      -4.669   1.479   0.655  1.00  0.00           C  
HETATM   27  O7  UNL     1      -4.989   2.717   1.175  1.00  0.00           O  
HETATM   28  C21 UNL     1      -3.966   3.687   1.297  1.00  0.00           C  
HETATM   29  C22 UNL     1      -5.672   0.520   0.532  1.00  0.00           C  
HETATM   30  O8  UNL     1      -6.938   0.861   0.940  1.00  0.00           O  
HETATM   31  H1  UNL     1      -5.357  -3.432   0.057  1.00  0.00           H  
HETATM   32  H2  UNL     1      -6.962  -3.534  -0.773  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.591  -2.756  -1.629  1.00  0.00           H  
HETATM   34  H4  UNL     1      -3.807  -1.983  -0.792  1.00  0.00           H  
HETATM   35  H5  UNL     1      -1.667  -0.345  -1.805  1.00  0.00           H  
HETATM   36  H6  UNL     1       0.624  -2.333  -0.745  1.00  0.00           H  
HETATM   37  H7  UNL     1       0.421  -1.523   0.911  1.00  0.00           H  
HETATM   38  H8  UNL     1       0.753  -0.080  -1.787  1.00  0.00           H  
HETATM   39  H9  UNL     1       1.516   1.670  -0.134  1.00  0.00           H  
HETATM   40  H10 UNL     1       2.792  -1.579   1.199  1.00  0.00           H  
HETATM   41  H11 UNL     1       3.862  -2.642   2.645  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.561  -3.624   1.182  1.00  0.00           H  
HETATM   43  H13 UNL     1       4.852  -4.111   2.409  1.00  0.00           H  
HETATM   44  H14 UNL     1       7.728  -0.420  -0.786  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.806   2.615  -2.558  1.00  0.00           H  
HETATM   46  H16 UNL     1       6.004   3.390  -1.492  1.00  0.00           H  
HETATM   47  H17 UNL     1       6.517   2.706  -3.057  1.00  0.00           H  
HETATM   48  H18 UNL     1       3.525   1.861  -1.165  1.00  0.00           H  
HETATM   49  H19 UNL     1      -0.855  -0.152   1.754  1.00  0.00           H  
HETATM   50  H20 UNL     1      -0.584   1.670   1.682  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.699   1.629  -0.738  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.577   1.911   0.342  1.00  0.00           H  
HETATM   53  H23 UNL     1      -3.091   3.250   1.826  1.00  0.00           H  
HETATM   54  H24 UNL     1      -3.618   4.022   0.300  1.00  0.00           H  
HETATM   55  H25 UNL     1      -4.351   4.587   1.824  1.00  0.00           H  
HETATM   56  H26 UNL     1      -7.702   0.216   0.877  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4   29
CONECT    4    5   34
CONECT    5    6   25   25
CONECT    6    7   24   35
CONECT    7    8
CONECT    8    9   36   37
CONECT    9   10   24   38
CONECT   10   11   22   39
CONECT   11   12   12   21
CONECT   12   13   40
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   41   42   43
CONECT   16   17   18
CONECT   17   44
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   45   46   47
CONECT   21   48
CONECT   22   23
CONECT   23   24   49   50
CONECT   24   51
CONECT   25   26   52
CONECT   26   27   29   29
CONECT   27   28
CONECT   28   53   54   55
CONECT   29   30
CONECT   30   56
END

HMDB0038928
     RDKit          3D
Lirioresinol A
 56 59  0  0  0  0  0  0  0  0999 V2000
   -6.0382   -2.9185   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533   -1.6538   -0.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3414   -0.7126    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0308   -1.0024   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417   -0.0474   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -0.3326   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.5481   -0.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -1.4933   -0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -0.1347   -0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    0.5732    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9798    0.1667    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905   -0.9697    0.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8337   -1.3441    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611   -2.5105    1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513   -3.2901    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7047   -0.5504   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -0.9472   -0.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    0.5970   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.3518   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8477    2.5397   -2.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892    0.9499   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    0.4863    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    0.6845    1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    0.6443   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712    1.1852    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6693    1.4786    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9891    2.7173    1.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    3.6866    1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6718    0.5200    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377    0.8612    0.9396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3571   -3.4325    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9615   -3.5337   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908   -2.7564   -1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -1.9828   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.3453   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6244   -2.3326   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213   -1.5230    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -0.0803   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6700   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7923   -1.5790    1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623   -2.6417    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -3.6241    1.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -4.1111    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7280   -0.4202   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    2.6151   -2.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037    3.3904   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5170    2.7057   -3.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    1.8608   -1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -0.1519    1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839    1.6703    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    1.6289   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5767    1.9108    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    3.2500    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    4.0225    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3508    4.5868    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7022    0.2161    0.8774 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  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 29 30  1  0
 29  3  1  0
 24  6  1  0
 24  9  1  0
 21 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 28 53  1  0
 28 54  1  0
 28 55  1  0
 30 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)	ChEBI
S(8-8)S	ChEBI
(+)-Episyringaresinol	HMDB
Symplicosigenol	HMDB
Syringaresinol	MeSH, HMDB
Syringa-resinol	MeSH, HMDB
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomer	MeSH, HMDB
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomer	MeSH, HMDB

Chemical Formula

C₂₂H₂₆O₈

Average Molecular Weight

418.437

Monoisotopic Molecular Weight

418.162767808

IUPAC Name

4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol

Traditional Name

syringaresinol

CAS Registry Number

21453-71-4

SMILES

COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3

InChI Key

KOWMJRJXZMEZLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Substituents

Furanoid lignan
Furofuran lignan skeleton
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Furofuran
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lignan (CHEBI:49211 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038928)
Cytoplasm (HMDB: HMDB0038928)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038928)

Source

Exogenous

Exogenous (HMDB: HMDB0038928)

Food

Food (HMDB: HMDB0038928)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0038928)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038928)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 211 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	88.36 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.23	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.03 m³·mol⁻¹	ChemAxon
Polarizability	43 Å³	ChemAxon
Number of Rings	4	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]+	196.832	31661259
DarkChem	[M-H]-	193.415	31661259
DeepCCS	[M+H]+	196.195	30932474
DeepCCS	[M-H]-	193.837	30932474
DeepCCS	[M-2H]-	227.76	30932474
DeepCCS	[M+Na]+	202.988	30932474
AllCCS	[M+H]+	200.0	32859911
AllCCS	[M+H-H2O]+	197.3	32859911
AllCCS	[M+NH4]+	202.5	32859911
AllCCS	[M+Na]+	203.2	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	204.0	32859911
AllCCS	[M+HCOO]-	204.9	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.	5.74 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4711 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2355.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	182.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.9 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	478.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1038.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	408.2 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	1166.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.1 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	12.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lirioresinol A	COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1	5085.8	Standard polar	33892256
Lirioresinol A	COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1	3353.3	Standard non polar	33892256
Lirioresinol A	COC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1	3749.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lirioresinol A,1TMS,isomer #1	COC1=CC(C2OCC3C(C4=CC(OC)=C(O[Si](C)(C)C)C(OC)=C4)OCC23)=CC(OC)=C1O	3481.8	Semi standard non polar	33892256
Lirioresinol A,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(OC)=CC(C2OCC3C(C4=CC(OC)=C(O[Si](C)(C)C)C(OC)=C4)OCC23)=C1	3426.4	Semi standard non polar	33892256
Lirioresinol A,1TBDMS,isomer #1	COC1=CC(C2OCC3C(C4=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OCC23)=CC(OC)=C1O	3745.7	Semi standard non polar	33892256
Lirioresinol A,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=CC(C2OCC3C(C4=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C4)OCC23)=C1	3897.1	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 - Lirioresinol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-1982000000-33ff9b96f717a6cbdd51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lirioresinol A GC-MS (2 TMS) - 70eV, Positive	splash10-052b-2096070000-90aaa198754bac5787a8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lirioresinol A 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Positive-QTOF	splash10-014i-0000900000-c2fea9ac570d65fb16a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Positive-QTOF	splash10-014r-0075900000-e62697a54d5f8d4b5ac6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Positive-QTOF	splash10-0udi-5900000000-c07121ca65cff3f586c5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Positive-QTOF	splash10-014i-0000900000-c2fea9ac570d65fb16a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Positive-QTOF	splash10-014r-0075900000-e62697a54d5f8d4b5ac6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Positive-QTOF	splash10-0udi-5900000000-c07121ca65cff3f586c5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Positive-QTOF	splash10-014i-0000900000-c2fea9ac570d65fb16a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Positive-QTOF	splash10-014r-0075900000-e62697a54d5f8d4b5ac6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Positive-QTOF	splash10-0udi-5900000000-c07121ca65cff3f586c5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Negative-QTOF	splash10-014i-0000900000-58a345c7e13bfd692354	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Negative-QTOF	splash10-014i-0034900000-287f53100d59888eb2e0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Negative-QTOF	splash10-0ab9-2936000000-63cd67d7185fea1cc098	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Negative-QTOF	splash10-014i-0000900000-58a345c7e13bfd692354	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Negative-QTOF	splash10-014i-0034900000-287f53100d59888eb2e0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Negative-QTOF	splash10-0ab9-2936000000-63cd67d7185fea1cc098	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Negative-QTOF	splash10-014i-0000900000-58a345c7e13bfd692354	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Negative-QTOF	splash10-014i-0034900000-287f53100d59888eb2e0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Negative-QTOF	splash10-0ab9-2936000000-63cd67d7185fea1cc098	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Positive-QTOF	splash10-014i-0000900000-2859d81bb81159bc981b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Positive-QTOF	splash10-014i-0133900000-8d3f30e7c98a7d4d07aa	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Positive-QTOF	splash10-00kr-0496200000-297522aaeb8abe2e99ad	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 10V, Negative-QTOF	splash10-014i-0000900000-123dc6784d974ffacb59	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 20V, Negative-QTOF	splash10-0f79-0039200000-0a5b58078e104a129859	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lirioresinol A 40V, Negative-QTOF	splash10-000i-0092200000-6ede323068b3f2abe115	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100067

PDB ID

Not Available

ChEBI ID

49211

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1872761

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Lirioresinol A (HMDB0038928)

MOL for HMDB0038928 (Lirioresinol A)

3D MOL for HMDB0038928 (Lirioresinol A)

3D SDF for HMDB0038928 (Lirioresinol A)

3D-SDF for HMDB0038928 (Lirioresinol A)

PDB for HMDB0038928 (Lirioresinol A)

3D PDB for HMDB0038928 (Lirioresinol A)

SMILES for HMDB0038928 (Lirioresinol A)

INCHI for HMDB0038928 (Lirioresinol A)

Structure for HMDB0038928 (Lirioresinol A)

3D Structure for HMDB0038928 (Lirioresinol A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra