Marvin  01141314402D          

 14 15  0  0  0  0            999 V2000
   10.1180    0.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8293    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8293    1.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1180    1.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4068    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022    1.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6126    1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6200    0.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3051    0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3698   -0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5646   -0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3143   -1.5321    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  3  4  2  0  0  0  0
  7 10  1  0  0  0  0
  5  6  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  6  4  1  0  0  0  0
 12 13  1  0  0  0  0
  5  1  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <ID>
CHEBI:65801

> <NAME>
5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7a-dihydro- 2H-cyclopenta[b]pyran-6-one

> <DEFINITION>
An organic heterobicyclic compound that is 7,7a-dihydrocyclopenta[b]pyran-6(2H)-one substituted by a hydroxy group at position 5 and a prop-2-en-1-ylidene group at position 7 (the Z isomer). Isolated from the sponge Ulosa and ascidian Diplosoma virens, it exhibits antimicrobial activity and toxicity against HCT116 cells (human colorectal cancer cells) by triggering apoptotic cell death.

> <STAR>
3

> <SYNONYM>
Diplosoma ylidene 2

> <IUPAC_NAME>
(7Z)-5-hydroxy-7-(prop-2-en-1-ylidene)-7,7a-dihydrocyclopenta[b]pyran-6(2H)-one

> <FORMULA>
C11H10O3

> <MASS>
190.19530

> <MONOISOTOPIC_MASS>
190.06299

> <CHARGE>
0

> <SMILES>
OC1=C2C=CCOC2\C(=C\C=C)C1=O

> <INCHI>
InChI=1S/C11H10O3/c1-2-4-7-9(12)10(13)8-5-3-6-14-11(7)8/h2-5,11,13H,1,6H2/b7-4+

> <INCHIKEY>
CCVQPAZRNPBPPA-QPJJXVBHSA-N

> <REAXYS_REGISTRY_NUMBER>
15800347

> <PUBMED_CITATION>
18463568

$$$$