CHEBI:17663 - (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid

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ChEBI Name (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid
ChEBI ID CHEBI:17663
ChEBI ASCII Name (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid
Definition A carboxylic ester arising from the formal condensation of the alcoholic hydroxy group of one molecule of (3R)-3-hydroxybutanoic acid with the the carboxylic acid group of another. It is a sex pheromone in the European spider Linyphia triangularis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:318, CHEBI:18659
Supplier Information
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Formula C8H14O5
Net Charge 0
Average Mass 190.194
Monoisotopic Mass 190.08412
InChI InChI=1S/C8H14O5/c1-5(9)3-8(12)13-6(2)4-7(10)11/h5-6,9H,3-4H2,1-2H3,(H,10,11)/t5-,6-/m1/s1
InChIKey RILHUWWTCSDPAN-PHDIDXHHSA-N
SMILES O[C@@H](CC(O[C@@H](CC(O)=O)C)=O)C
Metabolite of Species Details
Micromonospora sp. RV43 (NCBI:txid1661387) See: PubMed
Annulohypoxylon truncatum (NCBI:txid327061) See: PubMed
Linyphia triangularis (NCBI:txid94031) 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): pheromone
A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) has functional parent butyric acid (CHEBI:30772)
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) has role fungal metabolite (CHEBI:76946)
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) has role pheromone (CHEBI:26013)
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) is a (3R)-3-hydroxybutanoic acid oligomer (CHEBI:140392)
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) is a carboxylic ester (CHEBI:33308)
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663) is conjugate acid of (R)-3-[(R)-3-hydroxybutanoyloxy]butanoate (CHEBI:10979)
Incoming (R)-3-[(R)-3-hydroxybutanoyloxy]butanoate (CHEBI:10979) is conjugate base of (R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid (CHEBI:17663)
IUPAC Name
(3R)-3-{[(3R)-3-hydroxybutanoyl]oxy}butanoic acid
Manual Xref Database
C04546 KEGG COMPOUND
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Registry Numbers Types Sources
6387163 Beilstein Registry Number Beilstein
6387163 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17810206 PubMed citation Europe PMC
Last Modified
08 March 2018