chrysopine (CHEBI:83079)

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ChEBI Name	chrysopine

ChEBI ID	CHEBI:83079

Definition	A spiroketal and δ-lactone resulting from the formal condensation of the carboxy group of L-glutamine with the anomeric hydroxy group of D-fructose and substitution of the 1-hydroxy group of the fructose by the α-amino group of the glutamine. It is found in crown gall tumours induced in chrysanthemums by Agrobacterium tumefaciens.

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

Supplier Information

Download	Molfile XML SDF

Formula

C11H18N2O7

Net Charge

Average Mass

290.26980

Monoisotopic Mass

290.11140

InChI

InChI=1S/C11H18N2O7/c12-7(15)2-1-5-10(18)20-11(4-13-5)9(17)8(16)6(14)3-19-11/h5-6,8-9,13-14,16-17H,1-4H2,(H2,12,15)/t5-,6+,8+,9-,11?/m0/s1

InChIKey

KPXUNMNRHZUNAN-NNBAOJFJSA-N

SMILES

NC(=O)CC[C@@H]1NCC2(OC[C@@H](O)[C@@H](O)[C@@H]2O)OC1=O

Metabolite of Species	Details
Chrysanthemum (NCBI:txid13422)	Found in root (BTO:0001188). Found in crown gall tumours induced by the soil bacterium Agrobacterium tumefaciens See: DOI

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):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. (via opine )

ChEBI Ontology
Outgoing	chrysopine (CHEBI:83079) has functional parent D-fructopyranose (CHEBI:37714) chrysopine (CHEBI:83079) has functional parent L-glutamine (CHEBI:18050) chrysopine (CHEBI:83079) has role plant metabolite (CHEBI:76924) chrysopine (CHEBI:83079) is a δ-lactone (CHEBI:18946) chrysopine (CHEBI:83079) is a amino acid opine (CHEBI:83229) chrysopine (CHEBI:83079) is a carboxamide (CHEBI:37622) chrysopine (CHEBI:83079) is a secondary amino compound (CHEBI:50995) chrysopine (CHEBI:83079) is a spiroketal (CHEBI:72600) chrysopine (CHEBI:83079) is a triol (CHEBI:27136)

Incoming	α-chrysopine (CHEBI:83080) is a chrysopine (CHEBI:83079) β-chrysopine (CHEBI:83081) is a chrysopine (CHEBI:83079)

IUPAC Name

3-[(3S,9R,10R,11S)-9,10,11-trihydroxy-2-oxo-1,7-dioxa-4-azaspiro[5.5]undec-3-yl]propanamide

Registry Number	Type	Source
7384218	Reaxys Registry Number	Reaxys

Last Modified

03 October 2014