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CHEBI:79230 - bhas#20

ChEBI IDCHEBI:79230
ChEBI Namebhas#20
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#20 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.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H34O7
Net Charge0
Average Mass362.463
Monoisotopic Mass362.23045
SMILESC[C@H](CCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C18H34O7/c1-12(24-18-16(21)11-15(20)13(2)25-18)8-6-4-3-5-7-9-14(19)10-17(22)23/h12-16,18-21H,3-11H2,1-2H3,(H,22,23)/t12-,13+,14-,15-,16-,18-/m1/s1
InChIKeyLOQQYUUEPVHUQQ-RDEONCLASA-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)
bhas#20 (CHEBI:79230) has functional parent (3R,11R)-3,11-dihydroxylauric acid (CHEBI:79243)
bhas#20 (CHEBI:79230) has functional parent ascr#20 (CHEBI:78958)
bhas#20 (CHEBI:79230) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#20 (CHEBI:79230) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#20 (CHEBI:79230) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#20 (CHEBI:79230) is a monocarboxylic acid (CHEBI:25384)
bhas#20 (CHEBI:79230) is conjugate acid of bhas#20(1-) (CHEBI:139738)
Incoming Relation(s)
ibha#20 (CHEBI:79355) has functional parent bhas#20 (CHEBI:79230)
bhas#20(1-) (CHEBI:139738) is conjugate base of bhas#20 (CHEBI:79230)
IUPAC Name 
(3R,11R)-11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxydodecanoic acid
Synonym  Source
3R-hydroxy-11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
Manual XrefsDatabases
bhas%2320%0DSMID
Registry NumbersSources
Reaxys:22233424Reaxys
CAS:1355682-54-0SMID
Citations