CHEBI:15805 - D-octopine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name D-octopine
ChEBI ID CHEBI:15805
ChEBI ASCII Name D-octopine
Definition The (1R)-1-carboxyethyl derivative of L-arginine. It is a metabolite released by plant tumours.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7366, CHEBI:12631, CHEBI:21810
Supplier Information ChemicalBook:CB9226645, eMolecules:478552, ZINC000001532525
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Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2−) and both the amino and guanidino groups are protonated, resulting in a cation. Only the l-arginine (symbol Arg or R) enantiomer is found naturally. Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the precursor for the biosynthesis of nitric oxide. Like all amino acids, it is a white, water-soluble solid. The one-letter symbol R was assigned to arginine for its phonetic similarity.
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Formula C9H18N4O4
Net Charge 0
Average Mass 246.26360
Monoisotopic Mass 246.13281
InChI InChI=1S/C9H18N4O4/c1-5(7(14)15)13-6(8(16)17)3-2-4-12-9(10)11/h5-6,13H,2-4H2,1H3,(H,14,15)(H,16,17)(H4,10,11,12)/t5-,6+/m1/s1
InChIKey IMXSCCDUAFEIOE-RITPCOANSA-N
SMILES C[C@@H](N[C@@H](CCCNC(N)=N)C(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via opine )
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ChEBI Ontology
Outgoing D-octopine (CHEBI:15805) has role animal metabolite (CHEBI:75767)
D-octopine (CHEBI:15805) has role xenobiotic metabolite (CHEBI:76206)
D-octopine (CHEBI:15805) is a D-arginine derivative (CHEBI:83966)
D-octopine (CHEBI:15805) is a amino acid opine (CHEBI:83229)
D-octopine (CHEBI:15805) is a amino dicarboxylic acid (CHEBI:36164)
D-octopine (CHEBI:15805) is a guanidines (CHEBI:24436)
D-octopine (CHEBI:15805) is a secondary amino compound (CHEBI:50995)
D-octopine (CHEBI:15805) is conjugate acid of D-octopine(1−) (CHEBI:67037)
D-octopine (CHEBI:15805) is tautomer of D-octopine dizwitterion (CHEBI:57520)
Incoming D-octopine(1−) (CHEBI:67037) is conjugate base of D-octopine (CHEBI:15805)
D-octopine dizwitterion (CHEBI:57520) is tautomer of D-octopine (CHEBI:15805)
IUPAC Name
N2-[(1R)-1-carboxyethyl]-L-arginine
Synonyms Sources
Arginine, N2-(1-carboxyethyl)-, L- KEGG COMPOUND
D-(+)-Octopine KEGG COMPOUND
D-Octopine KEGG COMPOUND
D-octopine IUBMB
L-Arginine, N2-(1-carboxyethyl)-, (R)- KEGG COMPOUND
L-Arginine, N2-[(1R)-1-carboxyethyl]- KEGG COMPOUND
N2-(1-Carboxyethyl)-L-arginine KEGG COMPOUND
N2-(D-1-Carboxyethyl)-L-arginine KEGG COMPOUND
N2-(D-1-Carboxyethyl)-L-arginine KEGG COMPOUND
N2-(D-1-carboxyethyl)-L-arginine IUBMB
Octopine KEGG COMPOUND
Manual Xrefs Databases
C00001549 KNApSAcK
C04137 KEGG COMPOUND
CPD-309 MetaCyc
Octopine Wikipedia
View more database links
Registry Numbers Types Sources
1729145 Reaxys Registry Number Reaxys
34522-32-2 CAS Registry Number KEGG COMPOUND
34522-32-2 CAS Registry Number ChemIDplus
Citations Types Sources
16662161 PubMed citation Europe PMC
22496288 PubMed citation Europe PMC
8188582 PubMed citation Europe PMC
Last Modified
02 December 2014