Mrv0541 06301416012D          

 28 30  0  0  0  0            999 V2000
   13.7102   -3.8397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7102   -4.6617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9982   -3.4286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9982   -5.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2863   -3.8397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2863   -4.6617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5743   -3.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5719   -5.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4246   -5.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4246   -3.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1354   -2.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4234   -2.6113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7114   -2.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7076   -1.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4208   -0.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4171   -0.1436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1346   -1.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8341   -4.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0953   -5.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8411   -3.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997   -5.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3226   -4.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1678   -6.0705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7493   -5.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0669   -3.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2378   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9203   -5.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6645   -4.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  5  7  1  6  0  0  0
  6  8  1  1  0  0  0
  2  9  1  6  0  0  0
  1 10  1  1  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 19  2  0  0  0  0
 22 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 22  1  0  0  0  0
 24 22  2  0  0  0  0
 26 25  2  0  0  0  0
 27 24  1  0  0  0  0
 28 26  1  0  0  0  0
 28 27  2  0  0  0  0
M  END
> <ID>
CHEBI:79028

> <NAME>
icas#9

> <DEFINITION>
A 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (4R)-4-hydroxypentanoic acid. It is a metabolite of the nematode Caenorhabditis elegans.

> <STAR>
3

> <SYNONYM>
IC-asc-C5; (4R)-4-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy}valeric acid

> <IUPAC_NAME>
(4R)-4-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy}pentanoic acid

> <FORMULA>
C20H25NO7

> <MASS>
391.41500

> <MONOISOTOPIC_MASS>
391.16310

> <CHARGE>
0

> <SMILES>
C[C@H](CCC(O)=O)O[C@@H]1O[C@@H](C)[C@@H](C[C@H]1O)OC(=O)c1c[nH]c2ccccc12

> <INCHI>
InChI=1S/C20H25NO7/c1-11(7-8-18(23)24)26-20-16(22)9-17(12(2)27-20)28-19(25)14-10-21-15-6-4-3-5-13(14)15/h3-6,10-12,16-17,20-22H,7-9H2,1-2H3,(H,23,24)/t11-,12+,16-,17-,20-/m1/s1

> <INCHIKEY>
GIZBXORWWXIWKX-VEZRURDRSA-N

> <CAS_REGISTRY_NUMBER>
1173933-40-8

> <REAXYS_REGISTRY_NUMBER>
19683527

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMFA13040128

> <SMID_ACCESSION>
icas%239%0D

> <PUBMED_CITATION>
19545143; 19665885; 21849976; 22239548; 22253572; 22503501; 22662967; 22665789; 22701701; 23213209; 23689506; 29863473

$$$$