Marvin  11161209052D          

 20 21  0  0  0  0            999 V2000
   15.2503   -5.8278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6577   -6.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0889   -7.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6482   -7.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2240   -7.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8000   -7.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2357   -6.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6580   -5.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9517   -6.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9377   -7.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2308   -8.3852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2508   -9.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9717   -9.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6786   -9.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6605   -8.3458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9178   -7.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1653   -5.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5427   -9.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3984   -8.3846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4862   -8.3431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
 15  5  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5  6  2  0  0  0  0
  3 16  2  0  0  0  0
  6  7  1  0  0  0  0
  1 17  1  1  0  0  0
  7  8  1  0  0  0  0
 12 18  1  6  0  0  0
  8  9  1  0  0  0  0
 11 19  1  1  0  0  0
  9  1  1  0  0  0  0
 15 20  1  6  0  0  0
M  END
> <ID>
CHEBI:65452

> <NAME>
aspergillide C

> <DEFINITION>
A macrolide that is 4,15-dioxabicyclo[9.3.1]pentadeca-9,12-dien-3-one substituted by a hydroxy group at position 14 and a methyl group at position 5 (the 1S,5S,9E,11R,14S stereoisomer). It is isolated from the marine-derived fungus Aspergillus ostianus and exhibits cytotoxic activity against mouse lymphocytic leukemia cells (L1210).

> <STAR>
3

> <SYNONYM>
(+)-asperigillide C

> <IUPAC_NAME>
(1S,5S,9E,11S,14S)-14-hydroxy-5-methyl-4,15-dioxabicyclo[9.3.1]pentadeca-9,12-dien-3-one

> <FORMULA>
C14H20O4

> <MASS>
252.30620

> <MONOISOTOPIC_MASS>
252.13616

> <CHARGE>
0

> <SMILES>
[H][C@@]12CC(=O)O[C@@H](C)CCC\C=C\[C@]([H])(O1)C=C[C@@H]2O

> <INCHI>
InChI=1S/C14H20O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6-8,10-13,15H,2-3,5,9H2,1H3/b6-4+/t10-,11-,12-,13-/m0/s1

> <INCHIKEY>
LXBFWPWKVZPNRA-NPZYAQMBSA-N

> <REAXYS_REGISTRY_NUMBER>
15805982

> <PUBMED_CITATION>
18078344; 19128025; 19661704; 19817392; 21629897

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