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CHEBI:79231 - bhas#22

ChEBI IDCHEBI:79231
ChEBI Namebhas#22
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#22 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
FormulaC19H36O7
Net Charge0
Average Mass376.490
Monoisotopic Mass376.24610
SMILESC[C@H](CCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C19H36O7/c1-13(25-19-17(22)12-16(21)14(2)26-19)9-7-5-3-4-6-8-10-15(20)11-18(23)24/h13-17,19-22H,3-12H2,1-2H3,(H,23,24)/t13-,14+,15-,16-,17-,19-/m1/s1
InChIKeyARJGFPSUJRWUSF-CQQDWVGSSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and maoc-1(hj13) and acox-1(ok2257) mutant worms. It is a major ascaroside in dhs-28(hj8) 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#22 (CHEBI:79231) has functional parent (3R,12R)-3,12-dihydroxytridecanoic acid (CHEBI:79244)
bhas#22 (CHEBI:79231) has functional parent ascr#22 (CHEBI:78960)
bhas#22 (CHEBI:79231) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#22 (CHEBI:79231) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#22 (CHEBI:79231) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#22 (CHEBI:79231) is a monocarboxylic acid (CHEBI:25384)
bhas#22 (CHEBI:79231) is conjugate acid of bhas#22(1-) (CHEBI:139741)
Incoming Relation(s)
ibha#22 (CHEBI:79356) has functional parent bhas#22 (CHEBI:79231)
bhas#22(1-) (CHEBI:139741) is conjugate base of bhas#22 (CHEBI:79231)
IUPAC Name 
(3R,12R)-12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxytridecanoic acid
Synonym  Source
3R-hydroxy-12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acidSMID
Manual XrefsDatabases
bhas%2322%0DSMID
Registry NumbersSources
Reaxys:22233432Reaxys
CAS:1355681-17-2SMID
Citations