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CHEBI:78834 - ascr#8

ChEBI IDCHEBI:78834
ChEBI Nameascr#8
Stars
DefinitionA carboxamide resulting from the formal condensation of the carboxy group of ascr#7 with the amino group of 4-aminobenzoic acid. A metabolite of the nematode Caenorhabditis elegans, it is dauer inducing and strongly male attracting.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H27NO7
Net Charge0
Average Mass393.436
Monoisotopic Mass393.17875
SMILESC[C@H](CC/C=C/C(=O)Nc1ccc(C(=O)O)cc1)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C20H27NO7/c1-12(27-20-17(23)11-16(22)13(2)28-20)5-3-4-6-18(24)21-15-9-7-14(8-10-15)19(25)26/h4,6-10,12-13,16-17,20,22-23H,3,5,11H2,1-2H3,(H,21,24)(H,25,26)/b6-4+/t12-,13+,16-,17-,20-/m1/s1
InChIKeyWMKIQPAVTRWYKZ-XPUFHXNMSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (19346493)
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.
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
ascr#8 (CHEBI:78834) has functional parent 4-aminobenzoic acid (CHEBI:30753)
ascr#8 (CHEBI:78834) has functional parent ascr#7 (CHEBI:78830)
ascr#8 (CHEBI:78834) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#8 (CHEBI:78834) has role pheromone (CHEBI:26013)
ascr#8 (CHEBI:78834) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#8 (CHEBI:78834) is a carboxamide (CHEBI:37622)
ascr#8 (CHEBI:78834) is a monocarboxylic acid (CHEBI:25384)
ascr#8 (CHEBI:78834) is conjugate acid of ascr#8(1-) (CHEBI:139713)
Incoming Relation(s)
ascr#8(1-) (CHEBI:139713) is conjugate base of ascr#8 (CHEBI:78834)
IUPAC Name 
4-({(2E,6R)-6-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hept-2-enoyl}amino)benzoic acid
Synonym  Source
N-(6'R-[3''R,5''R-dihydroxy-6''S-methyl-(2H)-tetrahydropyran-2'-yloxy]-2'E-heptenoyl)-4-aminobenzoic acidSMID
Manual XrefsDatabases
ascr%238%0DSMID
Registry NumbersSources
Reaxys:22233428Reaxys
CAS:1172120-40-9SMID
Citations