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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:53 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034119

Secondary Accession Numbers

HMDB34119

Metabolite Identification

Common Name

Sesamolin

Description

Sesamolin belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Sesamolin is found, on average, in the highest concentration within sesames (Sesamum orientale). Sesamolin has also been detected, but not quantified in, fats and oils and flaxseeds (Linum usitatissimum). This could make sesamolin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sesamolin.

Structure

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


  Mrv0541 05061307352D          

 27 32  0  0  0  0            999 V2000
    7.8307    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0961    1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8227    4.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8307    3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    2.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1583    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 15  2  0  0  0  0
 18  6  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22  7  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

HMDB0034119
     RDKit          3D
Sesamolin
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.8033    0.4210    0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440    1.0386    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8858    0.8784   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    0.0909   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2088   -0.5208   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3308   -0.3762   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -1.0155   -0.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -0.9610    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -2.2588    1.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -2.3608    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964   -1.1759    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -1.5766    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577   -0.6490    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -1.0482    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239   -0.2172    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138    1.0478    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218    1.4525    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497    0.6142   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.7691   -0.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    3.0415   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4707    2.0528    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -1.6214   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648   -0.9800   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.4655    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    0.0723   -2.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2894    1.1782   -2.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1500    1.3591   -0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636    0.5748    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3304    1.6457    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8681   -1.1425   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -0.3353    1.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8615   -3.2749    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -2.3826    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327   -0.5602    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530   -2.5973    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -2.0504    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3864   -0.5351    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106    0.9735   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287    4.0175    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7195    2.9870   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -0.0876   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628   -1.6122   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.6256    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3551    0.9206   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9353    2.0435   -2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  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
  4 25  1  0
 25 26  1  0
 26 27  1  0
  6  1  1  0
 24  8  1  0
 27  3  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  2 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 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  0
 26 44  1  0
 26 45  1  0
M  END


  Mrv0541 05061307352D          

 27 32  0  0  0  0            999 V2000
    7.8307    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0961    1.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8227    4.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8307    3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    2.1480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -0.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1583    3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023    4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 15  2  0  0  0  0
 18  6  1  0  0  0  0
 18 16  2  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22  7  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
 25  9  1  0  0  0  0
 25 17  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034119

> <DATABASE_NAME>
hmdb

> <SMILES>
C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2

> <INCHI_KEY>
ZZMNWJVJUKMZJY-UHFFFAOYSA-N

> <FORMULA>
C20H18O7

> <MOLECULAR_WEIGHT>
370.3527

> <EXACT_MASS>
370.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.59432378831447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[4-(2H-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.737558838333333

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7968570256106493

> <JCHEM_POLAR_SURFACE_AREA>
64.61000000000001

> <JCHEM_REFRACTIVITY>
90.546

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sesamolin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034119
     RDKit          3D
Sesamolin
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.8033    0.4210    0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440    1.0386    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8858    0.8784   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    0.0909   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2088   -0.5208   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3308   -0.3762   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -1.0155   -0.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -0.9610    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -2.2588    1.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -2.3608    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964   -1.1759    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -1.5766    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577   -0.6490    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -1.0482    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239   -0.2172    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138    1.0478    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218    1.4525    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497    0.6142   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.7691   -0.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    3.0415   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4707    2.0528    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -1.6214   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648   -0.9800   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.4655    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    0.0723   -2.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2894    1.1782   -2.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1500    1.3591   -0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636    0.5748    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3304    1.6457    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8681   -1.1425   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -0.3353    1.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8615   -3.2749    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -2.3826    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327   -0.5602    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530   -2.5973    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -2.0504    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3864   -0.5351    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106    0.9735   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287    4.0175    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7195    2.9870   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -0.0876   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628   -1.6122   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.6256    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3551    0.9206   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9353    2.0435   -2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  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
  4 25  1  0
 25 26  1  0
 26 27  1  0
  6  1  1  0
 24  8  1  0
 27  3  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  2 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 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  0
 26 44  1  0
 26 45  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      14.617   3.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.951   4.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.284   5.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.559   0.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.513   2.865   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.469   8.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.284   4.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.789   1.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.283   1.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.951   5.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.617   6.463   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.950   3.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.543   4.010   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.529  -0.626   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.095   6.724   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      14.938   7.970   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
CONECT    1    3   11                                                       
CONECT    2    4   12                                                       
CONECT    3    1   15                                                       
CONECT    4    2   16                                                       
CONECT    5   11   17                                                       
CONECT    6   12   18                                                       
CONECT    7   13   22                                                       
CONECT    8   14   21                                                       
CONECT    9   23   25                                                       
CONECT   10   24   26                                                       
CONECT   11    1    5   19                                                  
CONECT   12    2    6   27                                                  
CONECT   13    7   14   19                                                  
CONECT   14    8   13   20                                                  
CONECT   15    3   17   23                                                  
CONECT   16    4   18   24                                                  
CONECT   17    5   15   25                                                  
CONECT   18    6   16   26                                                  
CONECT   19   11   13   21                                                  
CONECT   20   14   22   27                                                  
CONECT   21    8   19                                                       
CONECT   22    7   20                                                       
CONECT   23    9   15                                                       
CONECT   24   10   16                                                       
CONECT   25    9   17                                                       
CONECT   26   10   18                                                       
CONECT   27   12   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

COMPND    HMDB0034119
HETATM    1  C1  UNL     1      -3.803   0.421   0.752  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.044   1.039   0.714  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.886   0.878  -0.371  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.444   0.091  -1.394  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.209  -0.521  -1.351  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.331  -0.376  -0.261  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.119  -1.015  -0.289  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.177  -0.961   0.696  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.949  -2.259   1.163  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.322  -2.361   1.633  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.096  -1.176   1.155  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.235  -1.577   0.256  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.358  -0.649   0.441  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.453  -1.048   1.173  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.524  -0.217   1.372  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.514   1.048   0.831  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.422   1.452   0.098  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.350   0.614  -0.098  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.703   2.769  -0.315  1.00  0.00           O  
HETATM   20  C17 UNL     1       6.042   3.042  -0.027  1.00  0.00           C  
HETATM   21  O4  UNL     1       6.471   2.053   0.897  1.00  0.00           O  
HETATM   22  O5  UNL     1       1.762  -1.621  -1.038  1.00  0.00           O  
HETATM   23  C18 UNL     1       0.565  -0.980  -1.117  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.180  -0.465   0.230  1.00  0.00           C  
HETATM   25  O6  UNL     1      -6.454   0.072  -2.378  1.00  0.00           O  
HETATM   26  C20 UNL     1      -7.289   1.178  -2.090  1.00  0.00           C  
HETATM   27  O7  UNL     1      -7.150   1.359  -0.682  1.00  0.00           O  
HETATM   28  H1  UNL     1      -3.164   0.575   1.635  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.330   1.646   1.554  1.00  0.00           H  
HETATM   30  H3  UNL     1      -3.868  -1.142  -2.166  1.00  0.00           H  
HETATM   31  H4  UNL     1      -1.489  -0.335   1.546  1.00  0.00           H  
HETATM   32  H5  UNL     1       0.861  -3.275   1.290  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.249  -2.383   2.756  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.433  -0.560   2.016  1.00  0.00           H  
HETATM   35  H8  UNL     1       2.553  -2.597   0.548  1.00  0.00           H  
HETATM   36  H9  UNL     1       4.503  -2.050   1.623  1.00  0.00           H  
HETATM   37  H10 UNL     1       6.386  -0.535   1.950  1.00  0.00           H  
HETATM   38  H11 UNL     1       2.511   0.974  -0.682  1.00  0.00           H  
HETATM   39  H12 UNL     1       6.129   4.017   0.515  1.00  0.00           H  
HETATM   40  H13 UNL     1       6.720   2.987  -0.889  1.00  0.00           H  
HETATM   41  H14 UNL     1       0.668  -0.088  -1.794  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.263  -1.612  -1.493  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.252   0.626   0.339  1.00  0.00           H  
HETATM   44  H17 UNL     1      -8.355   0.921  -2.309  1.00  0.00           H  
HETATM   45  H18 UNL     1      -6.935   2.043  -2.656  1.00  0.00           H  
CONECT    1    2    2    6   28
CONECT    2    3   29
CONECT    3    4    4   27
CONECT    4    5   25
CONECT    5    6    6   30
CONECT    6    7
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

HMDB0034119
     RDKit          3D
Sesamolin
 45 50  0  0  0  0  0  0  0  0999 V2000
   -3.8033    0.4210    0.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440    1.0386    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8858    0.8784   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4439    0.0909   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2088   -0.5208   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3308   -0.3762   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -1.0155   -0.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -0.9610    0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -2.2588    1.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -2.3608    1.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964   -1.1759    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352   -1.5766    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577   -0.6490    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525   -1.0482    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5239   -0.2172    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138    1.0478    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218    1.4525    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497    0.6142   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.7691   -0.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    3.0415   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4707    2.0528    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620   -1.6214   -1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5648   -0.9800   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.4655    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4538    0.0723   -2.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2894    1.1782   -2.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1500    1.3591   -0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636    0.5748    1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3304    1.6457    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8681   -1.1425   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -0.3353    1.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8615   -3.2749    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -2.3826    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327   -0.5602    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5530   -2.5973    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -2.0504    1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3864   -0.5351    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106    0.9735   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287    4.0175    0.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7195    2.9870   -0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -0.0876   -1.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628   -1.6122   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.6256    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3551    0.9206   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9353    2.0435   -2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  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
  4 25  1  0
 25 26  1  0
 26 27  1  0
  6  1  1  0
 24  8  1  0
 27  3  1  0
 24 11  1  0
 18 13  1  0
 21 16  1  0
  1 28  1  0
  2 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 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  0
 26 44  1  0
 26 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Sesamolin	HMDB
Sesamolinol	HMDB

Chemical Formula

C₂₀H₁₈O₇

Average Molecular Weight

370.3527

Monoisotopic Molecular Weight

370.10525293

IUPAC Name

5-[4-(2H-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

Traditional Name

sesamolin

CAS Registry Number

526-07-8

SMILES

C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2

InChI Identifier

InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2

InChI Key

ZZMNWJVJUKMZJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Furofuran
Benzenoid
Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a lignan (CPD-8928 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034119)
Cytoplasm (HMDB: HMDB0034119)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034119)

Source

Exogenous

Food

Food (HMDB: HMDB0034119)

Herb and spice

Oilseed crop

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

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034119)

Not Available

Nutrient (HMDB: HMDB0034119)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.87 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	0.1 g/L	ALOGPS
logP	2.21	ALOGPS
logP	2.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	64.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.55 m³·mol⁻¹	ChemAxon
Polarizability	37.59 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
DarkChem	[M+H]+	184.621	31661259
DarkChem	[M-H]-	182.437	31661259
DeepCCS	[M+H]+	184.801	30932474
DeepCCS	[M-H]-	182.443	30932474
DeepCCS	[M-2H]-	216.833	30932474
DeepCCS	[M+Na]+	192.718	30932474
AllCCS	[M+H]+	187.1	32859911
AllCCS	[M+H-H2O]+	184.1	32859911
AllCCS	[M+NH4]+	189.8	32859911
AllCCS	[M+Na]+	190.6	32859911
AllCCS	[M-H]-	188.4	32859911
AllCCS	[M+Na-2H]-	187.7	32859911
AllCCS	[M+HCOO]-	187.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sesamolin	C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2	4228.2	Standard polar	33892256
Sesamolin	C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2	2843.5	Standard non polar	33892256
Sesamolin	C1OC2=C(O1)C=C(OC1OCC3C1COC3C1=CC3=C(OCO3)C=C1)C=C2	3177.1	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 - Sesamolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001a-2974000000-494fbc8fa2c180d2c6d8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sesamolin 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 - Sesamolin 10V, Positive-QTOF	splash10-00di-0219000000-5bd354cb876a5331196f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 20V, Positive-QTOF	splash10-008i-0597000000-5c7055b77affdc03747c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 40V, Positive-QTOF	splash10-000i-4920000000-e58ab0551a97d606a367	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 10V, Negative-QTOF	splash10-014i-0109000000-b9dd7b299397f3008c18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 20V, Negative-QTOF	splash10-0uy0-0249000000-b49ecb6e4a1b61549563	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 40V, Negative-QTOF	splash10-000j-2913000000-d9d9f42c1e33627d5184	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 10V, Negative-QTOF	splash10-014i-0009000000-582215453a9c988ec472	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 20V, Negative-QTOF	splash10-014r-0009000000-a214962399146e7b8a26	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 40V, Negative-QTOF	splash10-000i-0914000000-f13b1739843ebd3c145a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 10V, Positive-QTOF	splash10-00di-0109000000-531daf8442d0878cf060	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 20V, Positive-QTOF	splash10-00di-0239000000-545ab40c325794cc74b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sesamolin 40V, Positive-QTOF	splash10-0fe3-0589000000-4864364b33a1ad959eae	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

Not Available

FooDB ID

FDB012387

KNApSAcK ID

C00000639

Chemspider ID

509377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sesamolin

METLIN ID

Not Available

PubChem Compound

585998

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840661

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 Sesamolin (HMDB0034119)

MOL for HMDB0034119 (Sesamolin)

3D MOL for HMDB0034119 (Sesamolin)

3D SDF for HMDB0034119 (Sesamolin)

3D-SDF for HMDB0034119 (Sesamolin)

PDB for HMDB0034119 (Sesamolin)

3D PDB for HMDB0034119 (Sesamolin)

SMILES for HMDB0034119 (Sesamolin)

INCHI for HMDB0034119 (Sesamolin)

Structure for HMDB0034119 (Sesamolin)

3D Structure for HMDB0034119 (Sesamolin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra