Chemical Formula: C6H13N3O3

Chemical Formula C6H13N3O3

Found 27 metabolite its formula value is C6H13N3O3

Citrulline

(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acid

C6H13N3O3 (175.0956868)


Citrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine which is catalyzed by the enzyme ornithine carbamoyltransferase. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39). [Spectral] L-Citrulline (exact mass = 175.09569) and L-Glutamate (exact mass = 147.05316) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Occurs in the juice of watermelon (Citrullus vulgaris) IPB_RECORD: 257; CONFIDENCE confident structure KEIO_ID C013 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

   

Argininic acid

(2S)-5-carbamimidamido-2-hydroxypentanoic acid

C6H13N3O3 (175.0956868)


Tissue accumulation of argininic acid (AA) occurs in hyperargininemia. Hyperargininemia, an inborn error of the urea cycle, is caused by a severe deficiency of liver arginase, resulting in elevated tissue levels of arginine (Arg) and other guanidino compounds (GC). Affected patients present a neurological syndrome consisting of a variable degree of mental retardation, epilepsy and progressive spasticity whose pathophysiology is far from understood. Guanidino compounds accumulate in other pathological conditions such as uremia and epilepsy and some evidence supports the hypothesis that these compounds contribute to the neurological dysfunction characteristic of these diseases. The increase of these compounds occurs by blockage of the arginase reaction, activating secondary biochemical pathways. Thus, Arg is converted to α-keto-δ-guanidinovaleric acid by transamination, and this compound forms AA by hydrogenation. (PMID 12615083). AA has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Tissue accumulation of argininic acid (AA) occurs in hyperargininemia. Hyperargininemia, an inborn error of the urea cycle, is caused by a severe deficiency of liver arginase, resulting in elevated tissue levels of arginine (Arg) and other guanidino compounds (GC). Affected patients present a neurological syndrome consisting of a variable degree of mental retardation, epilepsy and progressive spasticity whose pathophysiology is far from understood. Guanidino compounds accumulate in other pathological conditions such as uremia and epilepsy and some evidence supports the hypothesis that these compounds contribute to the neurological dysfunction characteristic of these diseases. The increase of these compounds occurs by blockage of the arginase reaction, activating secondary biochemical pathways. Thus, Arg is converted to α-keto-δ-guanidinovaleric acid by transamination, and this compound forms AA by hydrogenation. (PMID 12615083) [HMDB]

   

D-Citrulline

2-amino-5-[(C-hydroxycarbonimidoyl)amino]pentanoic acid

C6H13N3O3 (175.0956868)


Citrullin, also known as cit or 2-amino-5-uredovaleric acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Citrullin is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Citrullin can be found in a number of food items such as cow milk, sesame, orange bell pepper, and pepper (c. frutescens), which makes citrullin a potential biomarker for the consumption of these food products. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite.

   

Carbamoyl (2R)-2,5-diaminopentanoate

[(2,5-Diaminopentanoyl)oxy]methanimidate

C6H13N3O3 (175.0956868)


   

Citrulline

L(+)-Citrulline

C6H13N3O3 (175.0956868)


COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

   
   

Citrulline

L(+)-Citrulline

C6H13N3O3 (175.0956868)


The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050 CONFIDENCE standard compound; ML_ID 29 L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

   

L-Citrulline

L(+)-Citrulline

C6H13N3O3 (175.0956868)


The L-enantiomer of citrulline. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

   

Citrulline; LC-tDDA; CE10

Citrulline; LC-tDDA; CE10

C6H13N3O3 (175.0956868)


   

Citrulline; LC-tDDA; CE20

Citrulline; LC-tDDA; CE20

C6H13N3O3 (175.0956868)


   

Citrulline; LC-tDDA; CE30

Citrulline; LC-tDDA; CE30

C6H13N3O3 (175.0956868)


   

Citrulline; LC-tDDA; CE40

Citrulline; LC-tDDA; CE40

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE0; CorrDec

Citrulline; AIF; CE0; CorrDec

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE10; CorrDec

Citrulline; AIF; CE10; CorrDec

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE30; CorrDec

Citrulline; AIF; CE30; CorrDec

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE0; MS2Dec

Citrulline; AIF; CE0; MS2Dec

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE10; MS2Dec

Citrulline; AIF; CE10; MS2Dec

C6H13N3O3 (175.0956868)


   

Citrulline; AIF; CE30; MS2Dec

Citrulline; AIF; CE30; MS2Dec

C6H13N3O3 (175.0956868)


   
   
   
   

O-(L-Norvalyl-5)-isourea

O-(L-Norvalyl-5)-isourea

C6H13N3O3 (175.0956868)


   

alpha-Amino-gamma-ureidovaleric acid

alpha-Amino-gamma-ureidovaleric acid

C6H13N3O3 (175.0956868)


   
   

L-citrulline zwitterion

L-citrulline zwitterion

C6H13N3O3 (175.0956868)


Zwitterionic form of L-citrulline having an anionic carboxy group and a protonated amino group; major species at pH 7.3.

   
   

DL-Citrulline

DL-Citrulline

C6H13N3O3 (175.0956868)


2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite.