CHEBI:16467 - L-arginine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name L-arginine
ChEBI ID CHEBI:16467
ChEBI ASCII Name L-arginine
Definition An L-α-amino acid that is the L-isomer of arginine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6185, CHEBI:13077, CHEBI:42927, CHEBI:21235
Supplier Information No supplier information found for this compound.
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Trimethylamine N-oxide (TMAO) is an organic compound with the formula (CH3)3NO. It is in the class of amine oxides. Although the anhydrous compound is known, trimethylamine N-oxide is usually encountered as the dihydrate. Both the anhydrous and hydrated materials are white, water-soluble solids. TMAO is found in the tissues of marine crustaceans and marine fish, where it prevents water pressure from distorting proteins and thus killing the animal. The concentration of TMAO increases with the depth at which the animal lives; TMAO is found in high concentrations in the deepest-living described fish species, Pseudoliparis swirei, which was found in the Mariana Trench, at a recorded depth of 8,076 m (26,496 ft). In animals, TMAO is a product of the oxidation of trimethylamine, a common metabolite of trimethyl quaternary ammonium compounds, like choline, trimethylglycine, and L-carnitine. High TMAO concentrations are associated with an increased risk of all-cause mortality and cardiovascular disease.
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Formula C6H14N4O2
Net Charge 0
Average Mass 174.20100
Monoisotopic Mass 174.11168
InChI InChI=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
InChIKey ODKSFYDXXFIFQN-BYPYZUCNSA-N
SMILES N[C@@H](CCCNC(N)=N)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) 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 )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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).
fundamental metabolite
Any metabolite produced by all living cells.
(via arginine )
Application(s): 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.
biomarker
A substance used as an indicator of a biological state.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 5-methyl-L-arginine (CHEBI:20604) has functional parent L-arginine (CHEBI:16467)
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)
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)
Nω-L-arginino group (CHEBI:32686) is substituent group from L-arginine (CHEBI:16467)
N2-L-arginino group (CHEBI:32685) 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
arginine KEGG DRUG
Synonyms Sources
(2S)-2-amino-5-(carbamimidamido)pentanoic acid IUPAC
(2S)-2-amino-5-guanidinopentanoic acid JCBN
(S)-2-amino-5-guanidinopentanoic acid ChEBI
(S)-2-Amino-5-guanidinovaleric acid KEGG COMPOUND
Arg DrugBank
L-(+)-arginine NIST Chemistry WebBook
L-Arg DrugBank
L-Arginin ChEBI
L-Arginine KEGG COMPOUND
R MetaCyc
Manual Xrefs Databases
1549 DrugCentral
ARG MetaCyc
ARG PDBeChem
C00001340 KNApSAcK
C00062 KEGG COMPOUND
D02982 KEGG DRUG
DB00125 DrugBank
ECMDB00517 ECMDB
GND PDBeChem
HMDB0000517 HMDB
L-arginine Wikipedia
YMDB00592 YMDB
View more database links
Registry Numbers Types Sources
1725413 Reaxys Registry Number Reaxys
74-79-3 CAS Registry Number KEGG COMPOUND
74-79-3 CAS Registry Number NIST Chemistry WebBook
74-79-3 CAS Registry Number ChemIDplus
83283 Gmelin Registry Number Gmelin
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Last Modified
24 December 2024