EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:79360 - ibha#30

ChEBI IDCHEBI:79360
ChEBI Nameibha#30
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is bhas#30 in which the hydroxy group at position 4 of the ascarylopyranose moiety has been has been converted to the corresponding 1H-indole-3-carboxylate ester. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC32H49NO8
Net Charge0
Average Mass575.743
Monoisotopic Mass575.34582
SMILESC[C@H](CCCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C32H49NO8/c1-22(15-11-9-7-5-3-4-6-8-10-12-16-24(34)19-30(36)37)39-32-28(35)20-29(23(2)40-32)41-31(38)26-21-33-27-18-14-13-17-25(26)27/h13-14,17-18,21-24,28-29,32-35H,3-12,15-16,19-20H2,1-2H3,(H,36,37)/t22-,23+,24-,28-,29-,32-/m1/s1
InChIKeyRHGNPNMYKQDMAV-VHJGPELESA-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)
ibha#30 (CHEBI:79360) has functional parent (3R,16R)-3,16-dihydroxymargaric acid (CHEBI:79249)
ibha#30 (CHEBI:79360) has functional parent bhas#30 (CHEBI:79235)
ibha#30 (CHEBI:79360) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#30 (CHEBI:79360) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#30 (CHEBI:79360) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#30 (CHEBI:79360) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#30 (CHEBI:79360) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,16R)-16-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyheptadecanoic acid
Synonyms  Source
3R-hydroxy-16R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptadecanoic acidSMID
3R-hydroxy-16R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-margaric acidChEBI
(3R,16R)-16-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxymargaric acidChEBI
Manual XrefsDatabases
ibha%2330SMID
Registry NumbersSources
Reaxys:22233535Reaxys
CAS:1355683-37-2SMID
Citations