CHEBI:78830 - ascr#7

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ChEBI Name ascr#7
ChEBI ID CHEBI:78830
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,6R)-6-hydroxyhept-2-enoic acid with ascarylopyranose (the α anomer). A metabolite of the nematode Caenorhabditis elegans, it is weakly dauer inducing and a weak male-attractant.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C13H22O6
Net Charge 0
Average Mass 274.31020
Monoisotopic Mass 274.14164
InChI InChI=1S/C13H22O6/c1-8(5-3-4-6-12(16)17)18-13-11(15)7-10(14)9(2)19-13/h4,6,8-11,13-15H,3,5,7H2,1-2H3,(H,16,17)/b6-4+/t8-,9+,10-,11-,13-/m1/s1
InChIKey GGHOMCWJOMBZEK-LHYQPRBASA-N
SMILES C[C@H](CC\C=C\C(O)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) 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.
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.
(via hydroxy fatty acid ascaroside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ascr#7 (CHEBI:78830) has functional parent (2E,6R)-6-hydroxyhept-2-enoic acid (CHEBI:78831)
ascr#7 (CHEBI:78830) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#7 (CHEBI:78830) has role pheromone (CHEBI:26013)
ascr#7 (CHEBI:78830) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#7 (CHEBI:78830) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#7 (CHEBI:78830) is conjugate acid of ascr#7(1-) (CHEBI:139710)
Incoming ascr#8 (CHEBI:78834) has functional parent ascr#7 (CHEBI:78830)
icas#7 (CHEBI:79023) has functional parent ascr#7 (CHEBI:78830)
ascr#7(1-) (CHEBI:139710) is conjugate base of ascr#7 (CHEBI:78830)
IUPAC Name
(2E,6R)-6-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hept-2-enoic acid
Synonym Source
6R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptenoic acid SMID
Manual Xref Database
ascr%237%0D SMID
View more database links
Registry Numbers Types Sources
1139837-37-8 CAS Registry Number SMID
22233384 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19346493 PubMed citation Europe PMC
19665885 PubMed citation Europe PMC
20135027 PubMed citation Europe PMC
20151418 PubMed citation Europe PMC
20422068 PubMed citation Europe PMC
21423575 PubMed citation Europe PMC
22239548 PubMed citation Europe PMC
22253572 PubMed citation Europe PMC
22503501 PubMed citation Europe PMC
22665789 PubMed citation Europe PMC
22701701 PubMed citation Europe PMC
Last Modified
25 July 2014