Ketcher 05221514522D 1   1.00000     0.00000     0

 16 16  0     0  0            999 V2000
   -2.3111    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3111    2.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    0.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772   -0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431   -0.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9092   -0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3111   -0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3111   -1.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772   -2.4222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451   -0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1530   -0.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -1.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -2.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451    0.5778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0     0  0
  1  3  1  0     0  0
  3  4  2  0     0  0
  4  5  1  0     0  0
  5  6  1  0     0  0
  4  7  1  0     0  0
  7  8  1  0     0  0
  8  9  1  0     0  0
  7 10  2  0     0  0
 10 11  1  0     0  0
 11 12  1  0     0  0
 12 13  1  0     0  0
 11 14  2  0     0  0
 14 15  1  0     0  0
 10 16  1  0     0  0
 16  1  1  0     0  0
M  END
> <ID>
CHEBI:68766

> <NAME>
chaetoglocin A

> <DEFINITION>
A member of the class of 2-pyranones that is 2H-pyran-2-one substituted by a (2E)-1-hydroxybut-2-en-2-yl group at position 6, a hydroxymethyl group at position 5 and a methoxy group at position 4. It has been isolated from the solid-fermentation culture of Chaetomium globosum and has been shown to exhibit antibacterial activity.

> <STAR>
3

> <IUPAC_NAME>
6-[(2E)-1-hydroxybut-2-en-2-yl]-5-(hydroxymethyl)-4-methoxy-2H-pyran-2-one

> <FORMULA>
C11H14O5

> <MASS>
226.22590

> <MONOISOTOPIC_MASS>
226.08412

> <CHARGE>
0

> <SMILES>
COc1cc(=O)oc(\C(CO)=C\C)c1CO

> <INCHI>
InChI=1S/C11H14O5/c1-3-7(5-12)11-8(6-13)9(15-2)4-10(14)16-11/h3-4,12-13H,5-6H2,1-2H3/b7-3+

> <INCHIKEY>
DGBMMVBFYMZWHX-XVNBXDOJSA-N

> <REAXYS_REGISTRY_NUMBER>
22515443

> <PUBMED_CITATION>
20814854

$$$$