CHEBI:16467 - L-arginine

ChEBI IDCHEBI:16467
ChEBI NameL-arginine
Stars
ASCII NameL-arginine
DefinitionAn L-α-amino acid that is the L-isomer of arginine.
Secondary ChEBI IDsCHEBI:6185, CHEBI:13077, CHEBI:21235, CHEBI:42927
Last Modified29 September 2025
DownloadsMolfile
FormulaC6H14N4O2
Net Charge0
Average Mass174.204
Monoisotopic Mass174.11168
SMILESN=C(N)NCCC[C@H](N)C(=O)O
InChIInChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
InChIKeyODKSFYDXXFIFQN-BYPYZUCNSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562)
- PubMed (4877125)
- PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
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).
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 Roles:
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
fundamental metabolite  Any metabolite produced by all living cells.
Applications:
biomarker  A substance used as an indicator of a biological state.
nutraceutical  A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
ChEBI Ontology
Outgoing Relation(s)
L-arginine (CHEBI:16467) has role Escherichia coli metabolite (CHEBI:76971)
L-arginine (CHEBI:16467) has role biomarker (CHEBI:59163)
L-arginine (CHEBI:16467) has role micronutrient (CHEBI:27027)
L-arginine (CHEBI:16467) has role mouse metabolite (CHEBI:75771)
L-arginine (CHEBI:16467) has role nutraceutical (CHEBI:50733)
L-arginine (CHEBI:16467) is a L-α-amino acid (CHEBI:15705)
L-arginine (CHEBI:16467) is a arginine (CHEBI:29016)
L-arginine (CHEBI:16467) is a glutamine family amino acid (CHEBI:24318)
L-arginine (CHEBI:16467) is a proteinogenic amino acid (CHEBI:83813)
L-arginine (CHEBI:16467) is conjugate acid of L-argininate (CHEBI:32681)
L-arginine (CHEBI:16467) is conjugate base of L-argininium(1+) (CHEBI:32682)
L-arginine (CHEBI:16467) is enantiomer of D-arginine (CHEBI:15816)
Incoming Relation(s)
N-acyl-L-arginine (CHEBI:21645) has functional parent L-arginine (CHEBI:16467)
L-arginine derivative (CHEBI:83965) has functional parent L-arginine (CHEBI:16467)
L-arginyl-L-amino acid (CHEBI:134262) has functional parent L-arginine (CHEBI:16467)
5-methyl-L-arginine (CHEBI:20604) has functional parent L-arginine (CHEBI:16467)
Ala-Arg (CHEBI:137238) has functional parent L-arginine (CHEBI:16467)
Ala-Met-Ser-Arg (CHEBI:73376) has functional parent L-arginine (CHEBI:16467)
Arg-Asn-Gln-Arg (CHEBI:73397) has functional parent L-arginine (CHEBI:16467)
Arg-Asn-Gly-Ser (CHEBI:73399) has functional parent L-arginine (CHEBI:16467)
Arg-Asp-Asp (CHEBI:156342) has functional parent L-arginine (CHEBI:16467)
Arg-Asp-Gln-Ser (CHEBI:137242) has functional parent L-arginine (CHEBI:16467)
Arg-Gly (CHEBI:157792) has functional parent L-arginine (CHEBI:16467)
Arg-Lys-Cys-Gly (CHEBI:73401) has functional parent L-arginine (CHEBI:16467)
Arg-Phe-Phe-Cys (CHEBI:73402) has functional parent L-arginine (CHEBI:16467)
Arg-Pro (CHEBI:141419) has functional parent L-arginine (CHEBI:16467)
Arg-Thr-Cys-Cys (CHEBI:73404) has functional parent L-arginine (CHEBI:16467)
Arg-Thr-Thr-Asp (CHEBI:138503) has functional parent L-arginine (CHEBI:16467)
Arg-Trp-Pro (CHEBI:156080) has functional parent L-arginine (CHEBI:16467)
Arg-Trp-Ser-Tyr (CHEBI:73405) has functional parent L-arginine (CHEBI:16467)
Asn-Arg (CHEBI:145751) has functional parent L-arginine (CHEBI:16467)
Asp-Arg (CHEBI:73445) has functional parent L-arginine (CHEBI:16467)
Asp-Gln-Arg (CHEBI:73447) has functional parent L-arginine (CHEBI:16467)
Cys-Arg (CHEBI:157802) has functional parent L-arginine (CHEBI:16467)
Glu-Arg (CHEBI:157844) has functional parent L-arginine (CHEBI:16467)
Glu-Arg-Gly (CHEBI:162704) has functional parent L-arginine (CHEBI:16467)
Glu-Arg-Gly-Met (CHEBI:191942) has functional parent L-arginine (CHEBI:16467)
Glu-Arg-Gly-Met-Thr (CHEBI:191943) has functional parent L-arginine (CHEBI:16467)
Glu-Asp-Arg (CHEBI:156374) has functional parent L-arginine (CHEBI:16467)
Glu-Glu-Arg (CHEBI:144557) has functional parent L-arginine (CHEBI:16467)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has functional parent L-arginine (CHEBI:16467)
Glu-Trp-Asp-Arg (CHEBI:138509) has functional parent L-arginine (CHEBI:16467)
Gly-Arg-Pro (CHEBI:144473) has functional parent L-arginine (CHEBI:16467)
Leu-Arg (CHEBI:73528) has functional parent L-arginine (CHEBI:16467)
MI-1148 (CHEBI:167663) has functional parent L-arginine (CHEBI:16467)
Phe-Arg (CHEBI:73632) has functional parent L-arginine (CHEBI:16467)
Phe-Arg-Thr (CHEBI:144556) has functional parent L-arginine (CHEBI:16467)
poly(glycyl-L-arginine) (CHEBI:142891) has functional parent L-arginine (CHEBI:16467)
Pro-Arg (CHEBI:73645) has functional parent L-arginine (CHEBI:16467)
Pro-Arg-Pro (CHEBI:144903) has functional parent L-arginine (CHEBI:16467)
Val-Arg (CHEBI:73711) has functional parent L-arginine (CHEBI:16467)
L-arginine-d7 (CHEBI:192075) is a L-arginine (CHEBI:16467)
L-argininium(1+) (CHEBI:32682) is conjugate acid of L-arginine (CHEBI:16467)
L-argininate (CHEBI:32681) is conjugate base of L-arginine (CHEBI:16467)
D-arginine (CHEBI:15816) is enantiomer of L-arginine (CHEBI:16467)
N2-L-arginino group (CHEBI:32685) is substituent group from L-arginine (CHEBI:16467)
Nω-L-arginino group (CHEBI:32686) is substituent group from L-arginine (CHEBI:16467)
L-arginine residue (CHEBI:29952) is substituent group from L-arginine (CHEBI:16467)
L-arginyl group (CHEBI:32684) is substituent group from L-arginine (CHEBI:16467)
IUPAC Name 
L-arginine
INN  Source
arginineKEGG DRUG
Synonyms  Source
L-ArginineKEGG COMPOUND
(S)-2-Amino-5-guanidinovaleric acidKEGG COMPOUND
(2S)-2-amino-5-guanidinopentanoic acidJCBN
(S)-2-amino-5-guanidinopentanoic acidChEBI
L-ArgininChEBI
L-(+)-arginineNIST Chemistry WebBook
Manual XrefsDatabases
C00062KEGG COMPOUND
GNDPDBeChem
L-arginineWikipedia
ARGPDBeChem
D02982KEGG DRUG
DB00125DrugBank
HMDB0000517HMDB
ARGMetaCyc
C00001340KNApSAcK
YMDB00592YMDB
ECMDB00517ECMDB
1549DrugCentral
Registry NumbersSources
Gmelin:83283Gmelin
Reaxys:1725413Reaxys
CAS:74-79-3KEGG COMPOUND
CAS:74-79-3ChemIDplus
CAS:74-79-3NIST Chemistry WebBook
Citations