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

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

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ChEBI ID	CHEBI:17663
ChEBI Name	(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid
Stars
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.
Secondary ChEBI IDs	CHEBI:318, CHEBI:18659
Last Modified	8 March 2018
Downloads	Molfile

Formula	C8H14O5
Net Charge	0
Average Mass	190.195
Monoisotopic Mass	190.08412
SMILES	C[C@H](CC(=O)O)OC(=O)C[C@@H](C)O
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

Species of Metabolite	Component	Source	Comments
Annulohypoxylon truncatum (ncbitaxon:327061)	-	PubMed (14695807)
Linyphia triangularis (ncbitaxon:94031)	-	PubMed (17810206)
Micromonospora sp. RV43 (ncbitaxon:1661387)	-	PubMed (28355070)

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.

ChEBI Ontology

Outgoing Relation(s)
	(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 Relation(s)
Incoming Relation(s)	(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 Xrefs	Databases
C04546	KEGG COMPOUND

Registry Numbers	Sources
Reaxys:6387163	Reaxys

Citations