Marvin  11151216242D          

 20 21  0  0  0  0            999 V2000
    0.0901    2.8793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5024    2.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0712    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5120    0.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0641    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    2.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981    2.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7777    0.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.3217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0906   -0.5010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8116   -0.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186   -0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5006    0.3610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7577    1.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    3.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6175   -0.9288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7618    0.3222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3262    0.3638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  1  0  0  0
  9  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
 15  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  6  0  0  0
 12 13  1  0  0  0  0
 12 18  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 20  1  6  0  0  0
M  END
> <ID>
CHEBI:65450

> <NAME>
aspergillide A

> <DEFINITION>
A macrolide that is 4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one substituted by a hydroxy group at position 14 and a methyl group at position 5 (the 1R,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

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

> <FORMULA>
C14H22O4

> <MASS>
254.32210

> <MONOISOTOPIC_MASS>
254.15181

> <CHARGE>
0

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]([H])(CC(=O)O[C@@H](C)CCC\C=C\1)O2

> <INCHI>
InChI=1S/C14H22O4/c1-10-5-3-2-4-6-11-7-8-12(15)13(18-11)9-14(16)17-10/h4,6,10-13,15H,2-3,5,7-9H2,1H3/b6-4+/t10-,11-,12-,13+/m0/s1

> <INCHIKEY>
FDJDTDDUDZAAFP-GDHSIMSHSA-N

> <REAXYS_REGISTRY_NUMBER>
19982176

> <PUBMED_CITATION>
18078344; 20141226; 21064045; 21207589; 21370350

$$$$