Marvin  12181216512D          

 28 32  0  0  0  0            999 V2000
    9.4753  -21.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1666  -21.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1637  -20.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4735  -19.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7855  -21.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7822  -20.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0273  -20.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5637  -20.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0326  -21.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8759  -19.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5954  -20.3579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5580  -21.1850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3305  -21.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8487  -20.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3959  -20.1436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8664  -21.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8586  -22.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1387  -22.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5648  -23.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5694  -22.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5872  -19.5273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5501  -22.0094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6885  -19.3673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8408  -24.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1296  -23.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5122  -24.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8440  -25.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674  -24.9266    0.0000 O   0  0  0  0  0  0  0  0  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 11  1  0  0  0  0
  3  4  2  0  0  0  0
 12 16  1  0  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
  7  8  1  0  0  0  0
 17 18  2  0  0  0  0
 18 25  1  0  0  0  0
  8  9  1  0  0  0  0
 24 19  1  0  0  0  0
  9  5  1  0  0  0  0
 19 20  2  0  0  0  0
 20 17  1  0  0  0  0
  4  6  1  0  0  0  0
 11 21  1  6  0  0  0
  3 10  1  0  0  0  0
 12 22  1  1  0  0  0
  5  6  2  0  0  0  0
 15 23  1  1  0  0  0
 24 25  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1  2  2  0  0  0  0
  5  1  1  0  0  0  0
  2  3  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 24  1  0  0  0  0
M  END
> <ID>
CHEBI:65684

> <NAME>
(-)-cubebin

> <DEFINITION>
A lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities.

> <STAR>
3

> <SYNONYM>
beta-cubebin; 9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignan; 3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol; (8R,8'R,9S)-cubebin

> <IUPAC_NAME>
(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol

> <FORMULA>
C20H20O6

> <MASS>
356.36920

> <MONOISOTOPIC_MASS>
356.12599

> <CHARGE>
0

> <SMILES>
[H][C@@]1(CO[C@H](O)[C@]1([H])Cc1ccc2OCOc2c1)Cc1ccc2OCOc2c1

> <INCHI>
InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1

> <INCHIKEY>
DIYWRNLYKJKHAM-MDOVXXIYSA-N

> <CAS_REGISTRY_NUMBER>
18423-69-3

> <REAXYS_REGISTRY_NUMBER>
6489121

> <CHEMIDPLUS>
18423-69-3

> <KEGG_COMPOUND_ACCESSION>
C10549

> <KNAPSACK_ACCESSION>
C00002591

> <PUBMED_CITATION>
15467205; 17053932; 17236178; 21385598; 21941916

$$$$