Marvin  11201208522D          

 23 25  0  0  0  0            999 V2000
   -3.4139    1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4151    0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867    1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7021    2.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784   -0.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786    0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1288    2.0526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311    0.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -1.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204   -0.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423    0.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    1.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    2.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2556    2.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    1.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5065    2.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  1 12  1  0  0  0  0
  6  1  1  0  0  0  0
  2 13  1  0  0  0  0
  7  8  1  0  0  0  0
  9 14  2  0  0  0  0
  1  2  2  0  0  0  0
 10 15  2  0  0  0  0
  3  4  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4  5  1  0  0  0  0
 17 18  1  0  0  0  0
  2  3  1  0  0  0  0
 18 19  2  0  0  0  0
  8  9  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
 10 11  1  0  0  0  0
 18 22  1  0  0  0  0
 11  7  2  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <ID>
CHEBI:65473

> <NAME>
BE-23372M

> <DEFINITION>
A butenolide that is furan-2(3H)-one substituted by a 3,4-dihydroxybenzylidene group at position 3 and a 3,4-dihydroxyphenyl group at position 5 (the 3E stereoisomer). It is isolated from the fermentation broth of the fungal strain Rhizoctonia solani F23372 and has been found to possess significant tyrosine kinase inhibitory potential. It also inhibits the growth of A431 human epidermoid carcinoma and MKN-7 human stomach cancer cell lines.

> <STAR>
3

> <IUPAC_NAME>
(3E)-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)furan-2(3H)-one

> <FORMULA>
C17H12O6

> <MASS>
312.27360

> <MONOISOTOPIC_MASS>
312.06339

> <CHARGE>
0

> <SMILES>
Oc1ccc(cc1O)\C=C1/C=C(OC1=O)c1ccc(O)c(O)c1

> <INCHI>
InChI=1S/C17H12O6/c18-12-3-1-9(6-14(12)20)5-11-8-16(23-17(11)22)10-2-4-13(19)15(21)7-10/h1-8,18-21H/b11-5+

> <INCHIKEY>
TZBZGNPXKXHFKI-VZUCSPMQSA-N

> <CAS_REGISTRY_NUMBER>
145588-13-2

> <REAXYS_REGISTRY_NUMBER>
6849861

> <CHEMIDPLUS>
145588-13-2

> <PUBMED_CITATION>
8175480; 8175481

$$$$