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CHEBI:79373 - ibho#20

ChEBI IDCHEBI:79373
ChEBI Nameibho#20
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#20 in which the hydroxy group at position 4 of the ascarylopyranose moiety has been has been converted to the corresponding 1H-indole-3-carboxylate ester. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H39NO8
Net Charge0
Average Mass505.608
Monoisotopic Mass505.26757
SMILESC[C@@H]1O[C@@H](OCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C27H39NO8/c1-18-24(36-26(33)21-17-28-22-13-9-8-12-20(21)22)16-23(30)27(35-18)34-14-10-6-4-2-3-5-7-11-19(29)15-25(31)32/h8-9,12-13,17-19,23-24,27-30H,2-7,10-11,14-16H2,1H3,(H,31,32)/t18-,19+,23+,24+,27+/m0/s1
InChIKeyPQBBEOSMILPNLI-NKVODUSASA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) 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)
ibho#20 (CHEBI:79373) has functional parent (3R)-3,12-dihydroxylauric acid (CHEBI:79278)
ibho#20 (CHEBI:79373) has functional parent bhos#20 (CHEBI:79260)
ibho#20 (CHEBI:79373) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#20 (CHEBI:79373) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#20 (CHEBI:79373) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#20 (CHEBI:79373) is a monocarboxylic acid (CHEBI:25384)
ibho#20 (CHEBI:79373) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydodecanoic acid
Synonyms  Source
(3R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxylauric acidChEBI
3R-hydroxy-12-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
3R-hydroxy-12-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acidChEBI
Manual XrefsDatabases
ibho%2320%0DSMID
Registry NumbersSources
Reaxys:22233517Reaxys
CAS:1355683-43-0SMID
Citations