EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:79264 - bhos#28

ChEBI IDCHEBI:79264
ChEBI Namebhos#28
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is (3R)-3,16-dihydroxyhexadecanoic acid (oscr#28) in which the hydroxy group at position 16 has been converted to the corresponding ascaroside. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 September 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H42O7
Net Charge0
Average Mass418.571
Monoisotopic Mass418.29305
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C22H42O7/c1-17-19(24)16-20(25)22(29-17)28-14-12-10-8-6-4-2-3-5-7-9-11-13-18(23)15-21(26)27/h17-20,22-25H,2-16H2,1H3,(H,26,27)/t17-,18+,19+,20+,22+/m0/s1
InChIKeySNINRZCQHRQHTE-SXEONFLVSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8), daf-22(ok693), 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)
bhos#28 (CHEBI:79264) has functional parent (3R)-3,16-dihydroxyhexadecanoic acid (CHEBI:79287)
bhos#28 (CHEBI:79264) has functional parent oscr#28 (CHEBI:79150)
bhos#28 (CHEBI:79264) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhos#28 (CHEBI:79264) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhos#28 (CHEBI:79264) is a monocarboxylic acid (CHEBI:25384)
bhos#28 (CHEBI:79264) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
bhos#28 (CHEBI:79264) is conjugate acid of bhos#28(1-) (CHEBI:139805)
Incoming Relation(s)
bhos#28(1-) (CHEBI:139805) is conjugate base of bhos#28 (CHEBI:79264)
IUPAC Name 
(3R)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyhexadecanoic acid
Synonyms  Source
(3R)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxypalmitic acidChEBI
3R-hydroxy-16-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-palmitic acidChEBI
3R-hydroxy-16-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acidSMID
Manual XrefsDatabases
bhos%2328%0DSMID
Registry NumbersSources
Reaxys:22233474Reaxys
CAS:1355682-81-3SMID
Citations