General Information of MET (ID: META00128)
Name Ureidopropionic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3-(carbamoylamino)Propanoate; 3-(carbamoylamino)Propanoic acid; 3-Ureidopropanoate; 3-Ureidopropanoic acid; 3-Ureidopropionate; 3-Ureidopropionic acid; 3-[(Aminocarbonyl)amino]propanoate; 3-[(Aminocarbonyl)amino]propanoic acid; 3-ureido-Propionate; Carbamoyl-b-ala-OH; Carbamoyl-beta-ala-OH', N-(Aminocarbonyl)-'b-alanine, 'N-Carbamyl-b-alanine; Ion(-1) OF N-carbamoyl-beta-alanine; N-(AMINOCARBONYL)-BETA-alanine; N-Carbamoyl-beta-alanine; N-Carbamyl-beta-alanine; Ureidopropanoate; Ureidopropanoic acid; Ureidopropionate; b-Ureidopropionate; b-Ureidopropionic acid; beta-Ureidopropionic acid
Source Endogenous;Escherichia Coli Metabolite;Food;Microbial
Structure Type   Ureas  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Organic carbonic acids and derivatives
Ureas
PubChem CID
111
HMDB ID
HMDB0000026
Formula
C4H8N2O3
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
C02642
ChEBI ID
18261
FooDB ID
FDB030466
ChemSpider ID
109
Physicochemical Properties Molecular Weight 132.12 Topological Polar Surface Area 92.4
XlogP -1.5 Complexity 123
Heavy Atom Count 9 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
Ureidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-beta-alanine, belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Ureidopropionic acid is an intermediate in the metabolism of uracil. More specifically, it is a breakdown product of dihydrouracil and is produced by the enzyme dihydropyrimidase. It is further decomposed into beta-alanine via the enzyme beta-ureidopropionase. Ureidopropionic acid is essentially a urea derivative of beta-alanine. High levels of ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency. Enzyme deficiencies in pyrimidine metabolism are associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil. Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheat, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods.
Regulatory Network
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 [1]
                      Introduced Variation Knockout of Gcgr
                      Induced Change Ureidopropionic acid concentration: increase (FC = 1.7)
                      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 ureidopropionic acid levels compared with control group.
References
1 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.

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