General Information of MET (ID: META01398)
Name N-Caffeoyl putrescine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-Ureidobutanedioate; 2-Ureidobutanedioic acid; Carbamoylaspartic acid; Carbamylaspartic acid; L-N-Carbamoylaspartic acid; N-Carbamoylaspartate; N-Carbamoylaspartic acid; NCD; Carbamyl-DL-aspartate; Ureidosuccinic acid, (D)-isomer; Ureidosuccinic acid, maganeese (+2), (1:1) salt; Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer; N-Carbamoyl-D-aspartic acid; Ureidosuccinic acid, (L)-isomer; Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer
Source Aliphatic acyclic compounds
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
93072
HMDB ID
HMDB0000828
Formula
C5H8N2O5
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
C00438
DrugBank ID
DB04252
ChEBI ID
15859
FooDB ID
FDB031033
ChemSpider ID
84022
METLIN ID
5791
Physicochemical Properties Molecular Weight 176.13 Topological Polar Surface Area 130
XlogP -1.9 Complexity 214
Heavy Atom Count 12 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Function
Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ureidosuccinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ureidosuccinic acid exists in all living species, ranging from bacteria to humans. ureidosuccinic acid can be biosynthesized from carbamoyl phosphate and L-aspartic acid through the action of the enzyme cad protein. In humans, ureidosuccinic acid is involved in the metabolic disorder called the canavan disease pathway. Outside of the human body, Ureidosuccinic acid has been detected, but not quantified in, several different foods, such as pigeon pea, bog bilberries, yardlong beans, carobs, and lemon balms. This could make ureidosuccinic acid a potential biomarker for the consumption of these foods. The L-enantiomer N-carbamoylaspartic acid.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) 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 Overexpression of AN2
                      Induced Change N-Caffeoyl putrescine concentration: decrease (FC = 11.85)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of N-caffeoyl putrescine levels compared with control group.
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) 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 NAT1
                      Induced Change N-Caffeoyl putrescine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the decrease of N-caffeoyl putrescine levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.
2 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

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