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CHEBI:79229 - bhas#18

ChEBI IDCHEBI:79229
ChEBI Namebhas#18
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#18 in which the pro-R hydrogen that is β to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans as well as the sour paste nematode, Panagrellus redivivus.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H32O7
Net Charge0
Average Mass348.436
Monoisotopic Mass348.21480
SMILESC[C@H](CCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C17H32O7/c1-11(23-17-15(20)10-14(19)12(2)24-17)7-5-3-4-6-8-13(18)9-16(21)22/h11-15,17-20H,3-10H2,1-2H3,(H,21,22)/t11-,12+,13-,14-,15-,17-/m1/s1
InChIKeyNJSZAOQCCDFSCR-DZGCXMPZSA-N
Species of MetaboliteComponentSourceComments
Panagrellus redivivus (ncbitaxon:6233) - PubMed (23213209) Produced by male.
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and dhs-28(hj8), maoc-1(hj13), and acox-1(ok2257) 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)
bhas#18 (CHEBI:79229) has functional parent (3R,10R)-3,10-dihydroxyundecanoic acid (CHEBI:79242)
bhas#18 (CHEBI:79229) has functional parent ascr#18 (CHEBI:78955)
bhas#18 (CHEBI:79229) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#18 (CHEBI:79229) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#18 (CHEBI:79229) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#18 (CHEBI:79229) is a monocarboxylic acid (CHEBI:25384)
bhas#18 (CHEBI:79229) is conjugate acid of bhas#18(1-) (CHEBI:139733)
Incoming Relation(s)
ibha#18 (CHEBI:79354) has functional parent bhas#18 (CHEBI:79229)
bhas#18(1-) (CHEBI:139733) is conjugate base of bhas#18 (CHEBI:79229)
IUPAC Name 
(3R,10R)-10-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyundecanoic acid
Synonym  Source
3R-hydroxy-10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
Manual XrefsDatabases
bhas%2318%0DSMID
Registry NumbersSources
Reaxys:22233412Reaxys
CAS:1355682-52-8SMID
Citations