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CHEBI:79239 - bhas#38

ChEBI IDCHEBI:79239
ChEBI Namebhas#38
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#38 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
FormulaC27H52O7
Net Charge0
Average Mass488.706
Monoisotopic Mass488.37130
SMILESC[C@H](CCCCCCCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C27H52O7/c1-21(33-27-25(30)20-24(29)22(2)34-27)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-23(28)19-26(31)32/h21-25,27-30H,3-20H2,1-2H3,(H,31,32)/t21-,22+,23-,24-,25-,27-/m1/s1
InChIKeyLONSJLDZLUHCRR-LJNMJUOLSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22235948) A major ascaroside in dhs-28(hj8) and daf-22(ok693) mutant worms, also detected in 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#38 (CHEBI:79239) has functional parent (3R,20R)-3,20-dihydroxyhenicosanoic acid (CHEBI:79253)
bhas#38 (CHEBI:79239) has functional parent ascr#38 (CHEBI:78976)
bhas#38 (CHEBI:79239) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#38 (CHEBI:79239) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#38 (CHEBI:79239) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#38 (CHEBI:79239) is a monocarboxylic acid (CHEBI:25384)
bhas#38 (CHEBI:79239) is conjugate acid of bhas#38(1-) (CHEBI:139765)
Incoming Relation(s)
bhas#38(1-) (CHEBI:139765) is conjugate base of bhas#38 (CHEBI:79239)
IUPAC Name 
(3R,20R)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyhenicosanoic acid
Synonyms  Source
(3R,20R)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyheneicosanoic acidChEBI
3R-hydroxy-20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-henicosanoic acidSMID
3R-hydroxy-20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heneicosanoic acidChEBI
Manual XrefsDatabases
bhas%2338%0DSMID
Registry NumbersSources
Reaxys:22233521Reaxys
CAS:1355682-70-0SMID
Citations