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CHEBI:79235 - bhas#30

ChEBI IDCHEBI:79235
ChEBI Namebhas#30
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#30 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
FormulaC23H44O7
Net Charge0
Average Mass432.598
Monoisotopic Mass432.30870
SMILESC[C@H](CCCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C23H44O7/c1-17(29-23-21(26)16-20(25)18(2)30-23)13-11-9-7-5-3-4-6-8-10-12-14-19(24)15-22(27)28/h17-21,23-26H,3-16H2,1-2H3,(H,27,28)/t17-,18+,19-,20-,21-,23-/m1/s1
InChIKeyMUVQYJIVDRBMJO-XBTHPWMNSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms. It is a major ascaroside in dhs-28(hj8) and maoc-1(hj13) mutant worms and has been detected in daf-22(ok693) 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#30 (CHEBI:79235) has functional parent (3R,16R)-3,16-dihydroxymargaric acid (CHEBI:79249)
bhas#30 (CHEBI:79235) has functional parent ascr#30 (CHEBI:78968)
bhas#30 (CHEBI:79235) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#30 (CHEBI:79235) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#30 (CHEBI:79235) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#30 (CHEBI:79235) is a monocarboxylic acid (CHEBI:25384)
bhas#30 (CHEBI:79235) is conjugate acid of bhas#30(1-) (CHEBI:139753)
Incoming Relation(s)
ibha#30 (CHEBI:79360) has functional parent bhas#30 (CHEBI:79235)
bhas#30(1-) (CHEBI:139753) is conjugate base of bhas#30 (CHEBI:79235)
IUPAC Name 
(3R,16R)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyheptadecanoic acid
Synonym  Source
3R-hydroxy-16R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptadecanoic acidSMID
Manual XrefsDatabases
bhas%2330%0DSMID
Registry NumbersSources
Reaxys:22233484Reaxys
CAS:1355682-63-1SMID
Citations