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CHEBI:78745 - icas#20

ChEBI IDCHEBI:78745
ChEBI Nameicas#20
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (11R)-11-hydroxylauric acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC27H39NO7
Net Charge0
Average Mass489.609
Monoisotopic Mass489.27265
SMILESC[C@H](CCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C27H39NO7/c1-18(12-8-6-4-3-5-7-9-15-25(30)31)33-27-23(29)16-24(19(2)34-27)35-26(32)21-17-28-22-14-11-10-13-20(21)22/h10-11,13-14,17-19,23-24,27-29H,3-9,12,15-16H2,1-2H3,(H,30,31)/t18-,19+,23-,24-,27-/m1/s1
InChIKeyAFPJDDPSVYDRDB-DRONAGRDSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs28(hj8), acox-1(ok2257), and maoc-1(hj13) mutant worms.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
icas#20 (CHEBI:78745) has functional parent (11R)-11-hydroxylauric acid (CHEBI:78978)
icas#20 (CHEBI:78745) has functional parent ascr#20 (CHEBI:78958)
icas#20 (CHEBI:78745) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#20 (CHEBI:78745) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#20 (CHEBI:78745) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#20 (CHEBI:78745) is a monocarboxylic acid (CHEBI:25384)
Incoming Relation(s)
ibha#20 (CHEBI:79355) has functional parent icas#20 (CHEBI:78745)
IUPAC Name 
(11R)-11-[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyloxy]dodecanoic acid
Synonyms  Source
(11R)-11-({(2R,3R,5R,6S)-3-hydroxy-5-[(1H-indol-3-ylcarbonyl)oxy]-6-methyltetrahydro-2H-pyran-2-yl}oxy)dodecanoic acidIUPAC
11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
(11R)-11-[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyloxy]lauric acidChEBI
Manual XrefsDatabases
icas%2320%0DSMID
Registry NumbersSources
Reaxys:22233501Reaxys
CAS:1355683-09-8SMID
Citations