| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-05-11 18:54:32 UTC |
|---|
| Updated at | 2022-05-11 18:54:33 UTC |
|---|
| NP-MRD ID | NP0092006 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | O-Ureidohomoserine |
|---|
| Description | O-Ureidohomoserine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). The canavanine biosynthesis pathway is analogous to the animal Krebs-Henseleit ornithine-urea cycle. O-Ureidohomoserine is a very strong basic compound (based on its pKa). O-Ureidohomoserine is involved in the canavanine biosynthesis pathway. Outside of the human body, O-Ureidohomoserine has been detected, but not quantified in, several different foods, such as wax gourds, pine nuts, grapefruits, leeks, and quinoa. This could make O-ureidohomoserine a potential biomarker for the consumption of these foods. The canaline-dependent ornithine carbamyltransferase has been purified subsequently. It can be generated from the enzymatic reduction of canavaninosuccinate or enzymatic oxidation of L-canaline. Feeding experiments demonstrated the existence of enzyme activities of canaline-dependent ornithine carbamyltransferase, ureidohomoserine-dependent argininosuccinate synthetase, and canavaninosuccinate-dependent argininosuccinate lyase in Canavalia lineate. The synthesis of ureidohomoserine is probably the rate-limiting step. The ornithineurea cycle amino acids effectively counteracted both the additive and synergistic growth-inhibiting properties of the canaline-urea cycle compounds. Ureidohomoserine interacted with canaline or canavanine to affect synergistically L. Minor growth by enhancing individual canavanine or canaline toxicity and increasing the additive growth reduction caused by canavanine plus canaline. |
|---|
| Structure | InChI=1S/C5H11N3O4/c6-3(4(9)10)1-2-12-8-5(7)11/h3H,1-2,6H2,(H,9,10)(H3,7,8,11) |
|---|
| Synonyms | | Value | Source |
|---|
| alpha-Amino-gamma-ureidooxybutyric acid | HMDB | | O-((Aminocarbonyl)amino)-L-homoserine | HMDB | | O-Ureido-L-homoserine | HMDB | | 2-Amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoate | Generator | | O-Ureidohomoserine | MeSH |
|
|---|
| Chemical Formula | C5H11N3O4 |
|---|
| Average Mass | 177.1585 Da |
|---|
| Monoisotopic Mass | 177.07496 Da |
|---|
| IUPAC Name | 2-amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoic acid |
|---|
| Traditional Name | 2-amino-4-[(C-hydroxycarbonimidoylamino)oxy]butanoic acid |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | NC(CCONC(O)=N)C(O)=O |
|---|
| InChI Identifier | InChI=1S/C5H11N3O4/c6-3(4(9)10)1-2-12-8-5(7)11/h3H,1-2,6H2,(H,9,10)(H3,7,8,11) |
|---|
| InChI Key | SFYVZOSIAIZWQU-UHFFFAOYSA-N |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | Alpha amino acids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Alpha-amino acid
- Fatty acid
- Carbonic acid derivative
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Hydrocarbon derivative
- Organic oxide
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|