Marvin  09131208522D          

 26 29  0  0  0  0            999 V2000
    8.6931   -1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6931    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9779   -0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9804    0.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2668    0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5499    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5514   -0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2657   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4084    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4068   -0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1209   -1.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8373   -0.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1201    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8322    0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5402    0.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5422    1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8300    1.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1158    1.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2684    1.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8345   -1.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916    1.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6943   -1.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5560   -1.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2575    0.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8305    2.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8323    0.6156    0.0000 Cl  0  0  0  0  0  0  0  0  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
 11 12  2  0  0  0  0
  6 26  1  0  0  0  0
M  END
> <ID>
CHEBI:66252

> <NAME>
topopyrone A

> <DEFINITION>
A naphthochromene that is 4H-naphtho[2,3-h]chromene-4,7,12-trione substituted by a chloro group at position 10, hydroxy groups at positions 5, 9 and 11 and a methyl group at position 2. It is isolated from a fungal strain Phoma sp.BAUA2861 and acts as an inhibitor of the enzyme topoisomerase I.

> <STAR>
3

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

> <FORMULA>
C18H9ClO7

> <MASS>
372.71300

> <MONOISOTOPIC_MASS>
372.00368

> <CHARGE>
0

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

> <INCHI>
InChI=1S/C18H9ClO7/c1-5-2-8(20)13-9(21)3-7-12(18(13)26-5)16(24)11-6(15(7)23)4-10(22)14(19)17(11)25/h2-4,21-22,25H,1H3

> <INCHIKEY>
KUCMIJRMIDNZCP-UHFFFAOYSA-N

> <REAXYS_REGISTRY_NUMBER>
8730620

> <PUBMED_CITATION>
11099218; 11099219; 19097800; 22462811

$$$$