Details of Metabolite

General Information of MET (ID: META00029)
Name Citrulline
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-5-(carbamoylamino)pentanoate; (2S)-2-Amino-5-(carbamoylamino)pentanoic acid; (S)-2-Amino-5-(aminocarbonyl)aminopentanoate; (S)-2-Amino-5-(aminocarbonyl)aminopentanoic acid; (S)-2-Amino-5-ureidopentanoate; (S)-2-Amino-5-ureidopentanoic acid; 2-Amino-5-uredovalerate; 2-Amino-5-uredovaleric acid; 2-Amino-5-ureidovalerate; 2-Amino-5-ureidovaleric acid; Amino-ureidovalerate; Amino-ureidovaleric acid; CIR; Cit; Cytrulline; D-Ureidonorvaline; DL-Citrulline; Gammaureidonorvaline; H-Cit-OH; L(+)-2-Amino-5-ureidovalerate; L(+)-2-Amino-5-ureidovaleric acid; L(+)-Citrulline; L-2-Amino-5-ureido-valerate; L-2-Amino-5-ureido-valeric acid; L-2-Amino-5-ureidovaleric acid; L-Citrulline; L-Cytrulline; L-N5-Carbamoyl-ornithine; N()-Carbamylornithine; N(5)-(Aminocarbonyl)-DL-ornithine; N(5)-(Aminocarbonyl)-L-ornithine; N(delta)-Carbamylornithine; N-Carbamylornithine; N5-(Aminocarbonyl)-L-ornithine; N5-(Aminocarbonyl)-ornithine; N5-(Aminocarbonyl)ornithine; N5-Carbamoyl-L-ornithine; N5-Carbamoylornithine; N5-Carbamylornithine; ND-Carbamylornithine; Ndelta-carbamy-ornithine; Ndelta-carbamylornithine; Ngamma-carbamylornithine; Sitrulline; Ureidonorvaline; Ureidovalerate; Ureidovaleric acid; a-Amino-D-ureidovalerate; a-Amino-D-ureidovaleric acid; a-Amino-delta-ureidovalerate; a-Amino-delta-ureidovaleric acid; alpha-Amino-delta-ureidovaleric acid; alpha-Amino-gamma-ureidovalerate; alpha-Amino-gamma-ureidovaleric acid; delta-Ureidonorvaline
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug;Toxins/Pollutant;Cosmetic;Microbial
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
9750
HMDB ID
HMDB0000904
Formula
C6H13N3O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00327
DrugBank ID
DB00155
ChEBI ID
16349
FooDB ID
FDB011841
ChemSpider ID
9367
METLIN ID
16
Physicochemical Properties Molecular Weight 175.19 Topological Polar Surface Area 118
XlogP -4.3 Complexity 171
Heavy Atom Count 12 Rotatable Bond Count 5
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Function
Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS). In this reaction, arginine is first oxidized into N(omega)-hydroxyarginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide (EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Immunoglobulin (IMG)
            Cardiac myosin (MYBPC3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change MYBPC3 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the decrease of MYBPC3 protein expression compared with control group.
      Macroglobulin (MGL)
            Complement C3 (CO3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change C3 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the decrease of C3 protein expression compared with control group.
      Oxidoreductases (EC 1)
            Ferritin (FTH1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change FTH1 protein expression levels: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the decrease of FTH1 protein expression compared with control group.
      Transferases (EC 2)
            Coenzyme Q protein 8A (COQ8A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change COQ8A protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the increase of COQ8A protein expression compared with control group.
      Tropomyosin (Tmyo)
            Tropomyosin alpha-1 chain (TPM1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change TPM1 protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the increase of TPM1 protein expression compared with control group.
            Tropomyosin alpha-3 chain (TPM3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Citrulline addition (1336 hours)
                      Induced Change TPM3 protein expression levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that citrulline addition causes the increase of TPM3 protein expression compared with control group.
Full List of Protein(s) Regulating This Metabolite
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Gcgr
                      Induced Change Citrulline concentration: increase (FC = 3.3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 2 diabetes mellitus [ICD-11: 5A11]
                      Details It is reported that knockout of GCGR leads to the increase of citrulline levels compared with control group.
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change Citrulline concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of citrulline levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Citrulline concentration: decrease (FC = 0.34 / 0.51)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of citrulline levels compared with control group.
      Lyases (EC 4)
            Cystathionine gamma-lyase (CTH) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Knockout of Cth
                      Induced Change Citrulline concentration: increase (FC = 2.74)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Organic acid disorderss [ICD-11: 5C50]
                      Details It is reported that knockout of Cth leads to the increase of citrulline levels compared with control group.
            Fumarate hydratase (FH) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [6]
                      Introduced Variation Knockout of Fh
                      Induced Change Citrulline concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status hydronephrosis [ICD-11: GB56]
                      Details It is reported that knockout of FLNB leads to the increase of citrulline levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [7]
                      Introduced Variation Knockout of TP53
                      Induced Change Citrulline concentration: decrease (Log2 FC=0.78)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of citrulline levels compared with control group.
References
1 Citrulline Supplementation Induces Changes in Body Composition and Limits Age-Related Metabolic Changes in Healthy Male Rats. J Nutr. 2015 Jul;145(7):1429-37.
2 Polyomic profiling reveals significant hepatic metabolic alterations in glucagon-receptor (GCGR) knockout mice: implications on anti-glucagon therapies for diabetes. BMC Genomics. 2011 Jun 1;12:281.
3 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
4 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
5 Hydrogen Sulfide Is a Regulator of Hemoglobin Oxygen-Carrying Capacity via Controlling 2,3-BPG Production in Erythrocytes. Oxid Med Cell Longev. 2021 Feb 13;2021:8877691.
6 A role for cytosolic fumarate hydratase in urea cycle metabolism and renal neoplasia. Cell Rep. 2013 May 30;3(5):1440-8.
7 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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