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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 16:49:37 UTC

Update Date

2021-09-22 16:49:37 UTC

HMDB ID

HMDB0301745

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Episesaminol

Description

Episesaminol is a member of the class of compounds known as furanoid lignans. Furanoid lignans 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. Episesaminol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Episesaminol can be found in sesame, which makes episesaminol a potential biomarker for the consumption of this food product.

Structure

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


  Mrv1652309271714162D          

 29 34  0  0  1  0            999 V2000
    2.5552    0.8182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.7320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2042    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9186    1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5317    1.3994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3387    1.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    2.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4006    2.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9527    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7063    2.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6201    3.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8131    3.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6977    1.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358    0.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1962    0.6457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0167    0.5595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677   -0.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532   -0.5738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400   -0.0217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2332   -0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782   -0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -0.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482   -1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742    0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16  5  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  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  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
M  END

HMDB0301745
     RDKit          3D
Episesaminol
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.2042   -2.5069    0.9415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -1.3452    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -1.2321    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079   -0.0509   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896    1.0534   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    0.9410   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785   -0.2227    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -0.2676    0.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0611    1.0955    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.0627    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7928   -0.2070    0.5619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4942    0.0715   -0.7494 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9346   -0.0789   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456   -1.2952   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7939   -1.4274    0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6434   -0.3406    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556    0.8922   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    1.0181   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2004    1.7994   -0.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3800    1.1195    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062   -0.2000    0.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737   -0.8091   -1.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674   -1.0752   -1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.9302    0.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6484    2.0772   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9332    1.7661   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9166    0.3440   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145   -3.3377    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -2.0859    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    1.7919   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -0.5686    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.0713    2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.9614    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.7791    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    1.0903   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020   -2.1725   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759   -2.3800    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    1.9824   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    1.1623   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8521    1.5410    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558   -0.5424   -1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4684   -2.1831   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186   -1.9788    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9420    1.9035    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7600    2.2725   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 24  8  1  0
 27  4  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  3 29  1  0
  6 30  1  0
  8 31  1  1
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  1
 26 44  1  0
 26 45  1  0
M  END


  Mrv1652309271714162D          

 29 34  0  0  1  0            999 V2000
    2.5552    0.8182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.7320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2042    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9186    1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5317    1.3994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3387    1.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    2.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4006    2.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9527    1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7063    2.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6201    3.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8131    3.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6977    1.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358    0.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1962    0.6457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0167    0.5595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677   -0.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532   -0.5738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400   -0.0217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2332   -0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782   -0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -0.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482   -1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -1.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742    0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16  5  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  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  1  0  0  0  0
 26 27  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301745

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CO[C@@H](C3=CC4=C(OCO4)C=C3O)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O7/c21-14-5-18-17(26-9-27-18)4-11(14)20-13-7-22-19(12(13)6-23-20)10-1-2-15-16(3-10)25-8-24-15/h1-5,12-13,19-21H,6-9H2/t12-,13-,19+,20-/m0/s1

> <INCHI_KEY>
KQRXQIPRDKVZPW-ICCDWZQGSA-N

> <FORMULA>
C20H18O7

> <MOLECULAR_WEIGHT>
370.3527

> <EXACT_MASS>
370.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85695440993203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1R,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxol-5-ol

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.143134335666667

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.352988645058153

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7751975564756726

> <JCHEM_POLAR_SURFACE_AREA>
75.61000000000001

> <JCHEM_REFRACTIVITY>
91.72670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1R,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxol-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301745
     RDKit          3D
Episesaminol
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.2042   -2.5069    0.9415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -1.3452    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -1.2321    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079   -0.0509   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896    1.0534   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    0.9410   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785   -0.2227    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -0.2676    0.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0611    1.0955    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.0627    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7928   -0.2070    0.5619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4942    0.0715   -0.7494 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9346   -0.0789   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456   -1.2952   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7939   -1.4274    0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6434   -0.3406    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556    0.8922   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    1.0181   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2004    1.7994   -0.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3800    1.1195    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062   -0.2000    0.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737   -0.8091   -1.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674   -1.0752   -1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.9302    0.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6484    2.0772   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9332    1.7661   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9166    0.3440   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145   -3.3377    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -2.0859    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    1.7919   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -0.5686    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.0713    2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.9614    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.7791    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    1.0903   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020   -2.1725   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759   -2.3800    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    1.9824   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    1.1623   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8521    1.5410    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558   -0.5424   -1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4684   -2.1831   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186   -1.9788    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9420    1.9035    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7600    2.2725   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 24  8  1  0
 27  4  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  3 29  1  0
  6 30  1  0
  8 31  1  1
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  1
 26 44  1  0
 26 45  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  H   UNK     0       4.770   1.527   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.301   1.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.981   2.873   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.315   3.643   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.459   2.612   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.966   2.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.441   4.397   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.948   4.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.978   3.573   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.385   4.199   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.224   5.731   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.718   6.051   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.502   2.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.996   1.788   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.520   0.323   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.833   1.205   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       9.365   1.044   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       8.153  -0.301   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.819  -1.071   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.675  -0.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.169  -0.361   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.693  -1.825   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.186  -2.146   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.156  -1.001   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.251  -1.628   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.090  -3.159   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.416  -3.479   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.632   0.463   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.138   0.784   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    9   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14                                                            
CONECT   16    5    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28   24   29                                                       
CONECT   29   28   21                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

COMPND    HMDB0301745
HETATM    1  O1  UNL     1      -3.204  -2.507   0.942  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.680  -1.345   0.518  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.058  -1.232   0.233  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.608  -0.051  -0.216  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.790   1.053  -0.396  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.440   0.941  -0.118  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.878  -0.223   0.333  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.512  -0.268   0.866  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.061   1.095   0.885  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.259   1.063   1.135  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.793  -0.207   0.562  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.494   0.071  -0.749  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.935  -0.079  -0.458  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.446  -1.295  -0.113  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.794  -1.427   0.208  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.643  -0.341   0.183  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.156   0.892  -0.162  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.799   1.018  -0.480  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.200   1.799  -0.112  1.00  0.00           O  
HETATM   20  C17 UNL     1       7.380   1.119   0.213  1.00  0.00           C  
HETATM   21  O4  UNL     1       7.006  -0.200   0.459  1.00  0.00           O  
HETATM   22  O5  UNL     1       0.974  -0.809  -1.675  1.00  0.00           O  
HETATM   23  C18 UNL     1      -0.367  -1.075  -1.321  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.440  -0.930   0.140  1.00  0.00           C  
HETATM   25  O6  UNL     1      -5.648   2.077  -0.855  1.00  0.00           O  
HETATM   26  C20 UNL     1      -6.933   1.766  -0.270  1.00  0.00           C  
HETATM   27  O7  UNL     1      -6.917   0.344  -0.578  1.00  0.00           O  
HETATM   28  H1  UNL     1      -3.014  -3.338   1.214  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.737  -2.086   0.344  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.801   1.792  -0.252  1.00  0.00           H  
HETATM   31  H4  UNL     1      -1.542  -0.569   1.941  1.00  0.00           H  
HETATM   32  H5  UNL     1       0.387   1.071   2.273  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.804   1.961   0.725  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.441  -0.779   1.253  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.309   1.090  -1.127  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.802  -2.172  -0.078  1.00  0.00           H  
HETATM   37  H10 UNL     1       5.176  -2.380   0.496  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.417   1.982  -0.747  1.00  0.00           H  
HETATM   39  H12 UNL     1       8.110   1.162  -0.636  1.00  0.00           H  
HETATM   40  H13 UNL     1       7.852   1.541   1.143  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.056  -0.542  -1.957  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.468  -2.183  -1.555  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.319  -1.979   0.640  1.00  0.00           H  
HETATM   44  H17 UNL     1      -6.942   1.904   0.834  1.00  0.00           H  
HETATM   45  H18 UNL     1      -7.760   2.273  -0.734  1.00  0.00           H  
CONECT    1    2   28
CONECT    2    3    3    7
CONECT    3    4   29
CONECT    4    5    5   27
CONECT    5    6   25
CONECT    6    7    7   30
CONECT    7    8
CONECT    8    9   24   31
CONECT    9   10
CONECT   10   11   32   33
CONECT   11   12   24   34
CONECT   12   13   22   35
CONECT   13   14   14   18
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   18   38
CONECT   19   20
CONECT   20   21   39   40
CONECT   22   23
CONECT   23   24   41   42
CONECT   24   43
CONECT   25   26
CONECT   26   27   44   45
END

HMDB0301745
     RDKit          3D
Episesaminol
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.2042   -2.5069    0.9415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -1.3452    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -1.2321    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6079   -0.0509   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896    1.0534   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    0.9410   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785   -0.2227    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -0.2676    0.8662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0611    1.0955    0.8850 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    1.0627    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7928   -0.2070    0.5619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4942    0.0715   -0.7494 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9346   -0.0789   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456   -1.2952   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7939   -1.4274    0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6434   -0.3406    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556    0.8922   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    1.0181   -0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2004    1.7994   -0.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3800    1.1195    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062   -0.2000    0.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737   -0.8091   -1.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674   -1.0752   -1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.9302    0.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6484    2.0772   -0.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9332    1.7661   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9166    0.3440   -0.5781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145   -3.3377    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7365   -2.0859    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    1.7919   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -0.5686    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.0713    2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.9614    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -0.7791    1.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    1.0903   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020   -2.1725   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759   -2.3800    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    1.9824   -0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103    1.1623   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8521    1.5410    1.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558   -0.5424   -1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4684   -2.1831   -1.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186   -1.9788    0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9420    1.9035    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7600    2.2725   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  5 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 24  8  1  0
 27  4  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  3 29  1  0
  6 30  1  0
  8 31  1  1
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  1
 26 44  1  0
 26 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₇

Average Molecular Weight

370.3527

Monoisotopic Molecular Weight

370.10525293

IUPAC Name

6-[(1R,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxol-5-ol

Traditional Name

6-[(1R,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxol-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12CO[C@@H](C3=CC4=C(OCO4)C=C3O)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C20H18O7/c21-14-5-18-17(26-9-27-18)4-11(14)20-13-7-22-19(12(13)6-23-20)10-1-2-15-16(3-10)25-8-24-15/h1-5,12-13,19-21H,6-9H2/t12-,13-,19+,20-/m0/s1

InChI Key

KQRXQIPRDKVZPW-ICCDWZQGSA-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
Benzodioxole
Furofuran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tetrahydrofuran
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Sesame (FooDB: FOOD00170)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.98	ALOGPS
logP	2.14	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.73 m³·mol⁻¹	ChemAxon
Polarizability	36.86 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	188.14	32859911
AllCCS	[M+H-H2O]+	185.115	32859911
AllCCS	[M+Na]+	191.738	32859911
AllCCS	[M+NH4]+	190.936	32859911
AllCCS	[M-H]-	191.305	32859911
AllCCS	[M+Na-2H]-	190.865	32859911
AllCCS	[M+HCOO]-	190.537	32859911
DeepCCS	[M-2H]-	219.755	30932474
DeepCCS	[M+Na]+	195.516	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 10V, Positive-QTOF	splash10-00di-0019000000-fa17e98bbf31199838d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 20V, Positive-QTOF	splash10-00dl-0179000000-ffdc34116006e83bb9fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 40V, Positive-QTOF	splash10-0udr-5910000000-87944d2b29df9aec93ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 10V, Negative-QTOF	splash10-014i-0109000000-08f4f7637a1bd7ca8d2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 20V, Negative-QTOF	splash10-014r-0229000000-9808a9b2df8dc154f5bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 40V, Negative-QTOF	splash10-000j-3903000000-9c4c047e4b3ec74578ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 10V, Positive-QTOF	splash10-00di-0029000000-61027daeb6753fa66c37	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 20V, Positive-QTOF	splash10-00di-0119000000-c3a798551c9eb95f53d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 40V, Positive-QTOF	splash10-0udi-0459000000-6ce2d61b13b0c4067b12	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 10V, Negative-QTOF	splash10-014i-0009000000-9e0ce1bd7a0d0b2c428c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 20V, Negative-QTOF	splash10-014i-0009000000-59dd7cf597b736d2afc7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Episesaminol 40V, Negative-QTOF	splash10-014i-0019000000-ef107a95a64d8fe744cf	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

FooDB ID

FDB000334

KNApSAcK ID

Not Available

Chemspider ID

57579554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14150057

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Episesaminol (HMDB0301745)

MOL for HMDB0301745 (Episesaminol)

3D MOL for HMDB0301745 (Episesaminol)

3D SDF for HMDB0301745 (Episesaminol)

3D-SDF for HMDB0301745 (Episesaminol)

PDB for HMDB0301745 (Episesaminol)

3D PDB for HMDB0301745 (Episesaminol)

SMILES for HMDB0301745 (Episesaminol)

INCHI for HMDB0301745 (Episesaminol)

Structure for HMDB0301745 (Episesaminol)

3D Structure for HMDB0301745 (Episesaminol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra