validoxylamine A (CHEBI:131941)

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ChEBI Name	validoxylamine A

ChEBI ID	CHEBI:131941

Definition	An amino cyclitol that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C14H25NO8

Net Charge

Average Mass

335.351

Monoisotopic Mass

335.15802

InChI

InChI=1S/C14H25NO8/c16-3-5-1-7(11(20)13(22)9(5)18)15-8-2-6(4-17)10(19)14(23)12(8)21/h1,6-23H,2-4H2/t6-,7+,8+,9-,10-,11+,12+,13+,14+/m1/s1

InChIKey

YCJYNBLLJHFIIW-MBABXGOBSA-N

SMILES

C1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)N[C@@H]2[C@@H]([C@H]([C@@H](C(=C2)CO)O)O)O

Metabolite of Species	Details
Streptomyces hygroscopicus subsp. limoneus (NCBI:txid264445)	See: PubMed
Apis cerana (NCBI:txid7461)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. antibiotic insecticide animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of alpha,alpha-trehalase (EC 2.4.1.28).

Application(s):	antibiotic insecticide

ChEBI Ontology
Outgoing	validoxylamine A (CHEBI:131941) has functional parent validamine (CHEBI:30449) validoxylamine A (CHEBI:131941) has role animal metabolite (CHEBI:75767) validoxylamine A (CHEBI:131941) has role antibiotic insecticide (CHEBI:39208) validoxylamine A (CHEBI:131941) has role bacterial metabolite (CHEBI:76969) validoxylamine A (CHEBI:131941) has role EC 3.2.1.28 (α,α-trehalase) inhibitor (CHEBI:83762) validoxylamine A (CHEBI:131941) is a amino cyclitol (CHEBI:61689) validoxylamine A (CHEBI:131941) is a secondary amino compound (CHEBI:50995) validoxylamine A (CHEBI:131941) is conjugate base of validoxylamine A(1+) (CHEBI:111505)

Incoming	validoxylamine A(1+) (CHEBI:111505) is conjugate acid of validoxylamine A (CHEBI:131941)

IUPAC Name

(1S,2S,3R,6S)-4-(hydroxymethyl)-6-{[(1S,2S,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]amino}cyclohex-4-ene-1,2,3-triol

Synonym	Source
(+)-validoxylamine A	ChEBI

Last Modified

03 July 2018

General Comment
2016-05-17	See also: doi:10.1016/j.catcom.2005.10.004