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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB120499 |
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Identification |
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| Name: |
O-ureidohomoserine |
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| Description: | O-Ureidohomoserine is involved in the canavanine biosynthesis pathway. It can be generated from the enzymatic reduction of canavaninosuccinate or enzymatic oxidation of L-canaline. The canavanine biosynthesis pathway is analogous to the animal Krebs-Henseleit ornithine-urea cycle. 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 canaline-dependent ornithine carbamyltransferase has been purified subsequently. The synthesis of ureidohomoserine is probably the rate-limiting step. 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. The ornithineurea cycle amino acids effectively counteracted both the additive and synergistic growth-inhibiting properties of the canaline-urea cycle compounds.(PMID: 16659513 ). |
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Structure |
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| Synonyms: | - alpha-amino-gamma-Ureidooxybutyric acid
- O-((Aminocarbonyl)amino)-L-homoserine
- O-ureido-L-Homoserine
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Chemical Formula: |
C5H11N3O4 |
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| Average Molecular Weight: |
177.16 |
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| Monoisotopic Molecular
Weight: |
178.08278 |
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| InChI Key: |
SFYVZOSIAIZWQU-UHFFFAOYSA-N |
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| InChI: | 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) |
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| CAS
number: |
51767-67-0 |
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| IUPAC Name: | 2-amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoic acid |
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Traditional IUPAC Name: |
2-amino-4-[(C-hydroxycarbonimidoylamino)oxy]butanoic acid |
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| SMILES: | C(CC(C(=O)[O-])[N+])ONC(N)=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities 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). |
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Kingdom |
Chemical entities |
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| Super Class | Organic compounds |
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Class |
Organic acids and derivatives |
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| Sub Class | Carboxylic acids and derivatives |
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Direct Parent |
Alpha amino acids |
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| Alternative Parents |
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| 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
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| Molecular Framework |
Aliphatic acyclic compounds |
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| External Descriptors |
Not Available |
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Physical Properties |
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| State: |
Solid |
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| Charge: | 0 |
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Melting point: |
Not Available |
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| Experimental Properties: |
| Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Not Available |
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| Reactions: | |
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Pathways: |
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Spectra |
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| Spectra: |
Not Available |
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References |
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| References: |
- Rosenthal GA, Gulati DK, Sabharwal PS: Additive and Synergistic Growth-inhibiting Properties of the Canaline-Urea Cycle Amino Acids. Plant Physiol. 1976 Apr;57(4):493-6. [16659513 ]
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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