EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:17249 - D-nopaline

ChEBI IDCHEBI:17249
ChEBI NameD-nopaline
Stars
ASCII NameD-nopaline
DefinitionAn amino acid opine resulting from the formal reductive condensation of the amino group of L-arginine with the keto group of 2-oxopentanedioic acid.
Secondary ChEBI IDsCHEBI:4216, CHEBI:7365, CHEBI:7620, CHEBI:12630, CHEBI:21809
Last Modified16 May 2024
DownloadsMolfile
FormulaC11H20N4O6
Net Charge0
Average Mass304.303
Monoisotopic Mass304.13828
SMILESN=C(N)NCCC[C@H](N[C@H](CCC(=O)O)C(=O)O)C(=O)O
InChIInChI=1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m0/s1
InChIKeyLMKYZBGVKHTLTN-NKWVEPMBSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
D-nopaline (CHEBI:17249) is a D-glutamic acid derivative (CHEBI:83983)
D-nopaline (CHEBI:17249) is a L-arginine derivative (CHEBI:83965)
D-nopaline (CHEBI:17249) is a amino acid opine (CHEBI:83229)
D-nopaline (CHEBI:17249) is a guanidines (CHEBI:24436)
D-nopaline (CHEBI:17249) is a secondary amino compound (CHEBI:50995)
D-nopaline (CHEBI:17249) is a tricarboxylic acid (CHEBI:27093)
D-nopaline (CHEBI:17249) is conjugate acid of D-nopalinate(1−) (CHEBI:58074)
Incoming Relation(s)
D-nopalinate(1−) (CHEBI:58074) is conjugate base of D-nopaline (CHEBI:17249)
IUPAC Names 
N-[(1S)-4-carbamimidamido-1-carboxybutyl]-D-glutamic acid
(2R)-2-{[(1S)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid
Synonyms  Source
D-NopalineKEGG COMPOUND
N-[4-[(Aminoiminomethyl)amino]-1-carboxybutyl]-D-glutamic acid(ECL)KEGG COMPOUND
N2-(D-1,3-Dicarboxypropyl)-L-arginineKEGG COMPOUND
NopalineKEGG COMPOUND
N2-(D-1,3-dicarboxypropyl)-L-arginineIUBMB
(S)-N-(4-((Aminoiminomethyl)amino)-1-carboxybutyl)-D-glutamic acidChemIDplus
Manual XrefsDatabases
C01682KEGG COMPOUND
C00001548KNApSAcK
Registry NumbersSources
CAS:22350-70-5KEGG COMPOUND
CAS:22350-70-5ChemIDplus