CHEBI:79373 - ibho#20

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ibho#20
ChEBI ID CHEBI:79373
Definition An ω-hydroxy fatty acid ascaroside that is bhos#20 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C27H39NO8
Net Charge 0
Average Mass 505.60050
Monoisotopic Mass 505.26757
InChI InChI=1S/C27H39NO8/c1-18-24(36-26(33)21-17-28-22-13-9-8-12-20(21)22)16-23(30)27(35-18)34-14-10-6-4-2-3-5-7-11-19(29)15-25(31)32/h8-9,12-13,17-19,23-24,27-30H,2-7,10-11,14-16H2,1H3,(H,31,32)/t18-,19+,23+,24+,27+/m0/s1
InChIKey PQBBEOSMILPNLI-NKVODUSASA-N
SMILES C[C@@H]1O[C@@H](OCCCCCCCCC[C@@H](O)CC(O)=O)[C@H](O)C[C@H]1OC(=O)c1c[nH]c2ccccc12
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via hydroxy fatty acid ascaroside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ibho#20 (CHEBI:79373) has functional parent (3R)-3,12-dihydroxylauric acid (CHEBI:79278)
ibho#20 (CHEBI:79373) has functional parent bhos#20 (CHEBI:79260)
ibho#20 (CHEBI:79373) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#20 (CHEBI:79373) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
ibho#20 (CHEBI:79373) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#20 (CHEBI:79373) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#20 (CHEBI:79373) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydodecanoic acid
Synonyms Sources
(3R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxylauric acid ChEBI
3R-hydroxy-12-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acid SMID
3R-hydroxy-12-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acid ChEBI
Manual Xref Database
ibho%2320%0D SMID
View more database links
Registry Numbers Types Sources
1355683-43-0 CAS Registry Number SMID
22233517 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014