Marvin  10121215242D          

 25 28  0  0  0  0            999 V2000
   -2.1059   -8.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1059   -6.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -7.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -7.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5322   -6.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -7.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476   -7.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333   -8.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3906   -7.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3922   -7.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781   -8.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -7.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6789   -6.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333   -7.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -6.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -5.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310   -5.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832   -5.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -5.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645   -8.3823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074   -5.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046   -9.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7570   -8.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -7.1412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0315   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0  0  0  0
 12 14  1  0  0  0  0
 13  9  1  0  0  0  0
 13 14  2  0  0  0  0
  1 10  1  0  0  0  0
  5  6  2  0  0  0  0
  9  2  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8  3  1  0  0  0  0
  5 19  1  0  0  0  0
  4  2  1  0  0  0  0
  7 20  1  0  0  0  0
  3  4  2  0  0  0  0
  2 21  2  0  0  0  0
  9 10  2  0  0  0  0
  1 22  2  0  0  0  0
  3  1  1  0  0  0  0
 12 23  1  0  0  0  0
 10 11  1  0  0  0  0
 15 24  2  0  0  0  0
  4  5  1  0  0  0  0
 17 25  1  0  0  0  0
M  END
> <ID>
CHEBI:66254

> <NAME>
topopyrone C

> <DEFINITION>
A naphthochromene that is 4H-naphtho[2,3-h]chromene-4,7,12-trione substituted by hydroxy groups at positions 5, 9 and 11 and a methyl group at position 2. It is isolated from fungal strains Phoma and Penicillium and acts as an inhibitor of the enzyme topoisomerase I.

> <STAR>
3

> <IUPAC_NAME>
5,9,11-trihydroxy-2-methyl-4H-naphtho[2,3-h]chromene-4,7,12-trione

> <FORMULA>
C18H10O7

> <MASS>
338.26780

> <MONOISOTOPIC_MASS>
338.04265

> <CHARGE>
0

> <SMILES>
Cc1cc(=O)c2c(O)cc3C(=O)c4cc(O)cc(O)c4C(=O)c3c2o1

> <INCHI>
InChI=1S/C18H10O7/c1-6-2-10(20)15-12(22)5-9-14(18(15)25-6)17(24)13-8(16(9)23)3-7(19)4-11(13)21/h2-5,19,21-22H,1H3

> <INCHIKEY>
AWDAPFGGFWZKGB-UHFFFAOYSA-N

> <REAXYS_REGISTRY_NUMBER>
8728026

> <PUBMED_CITATION>
11099218; 11099219; 18248813

$$$$