| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 01:47:07 UTC |
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| Update date | 2019-11-26 03:21:29 UTC |
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| Primary ID | FDB028907 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB 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) [HMDB]. O-Ureidohomoserine is found in many foods, some of which are other bread, pineappple sage, common persimmon, and greenthread tea. |
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| CAS Number | 51767-67-0 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C5H11N3O4 |
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| IUPAC name | 2-amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoic acid |
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| 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) |
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| InChI Key | SFYVZOSIAIZWQU-UHFFFAOYSA-N |
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| Isomeric SMILES | NC(CCONC(O)=N)C(O)=O |
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| Average Molecular Weight | 177.1585 |
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| Monoisotopic Molecular Weight | 177.074955855 |
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| Classification |
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| 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). |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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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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| Ontology |
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| Disposition | Route of exposure: Source: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | O-Ureidohomoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9200000000-09018d8ebfc327cf6e32 | Spectrum | | Predicted GC-MS | O-Ureidohomoserine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9361000000-031b96a404c08397958f | Spectrum | | Predicted GC-MS | O-Ureidohomoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0m1i-2900000000-caf76614b9c4ed591726 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9600000000-f9253e2fdf27205b30cf | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-3de115bbc46c6215bcfd | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0059-2900000000-66b67d20b11e1030a2b2 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9300000000-41b0080d162a10f33641 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-7ceaac484332cd2488e1 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-054o-9100000000-a91ad1e4a8cccb430487 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052f-9200000000-2abda3789392ed608dfe | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-16d7c771f9c36fd94729 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-02di-1900000000-7a6d25877ba4e3db2ab9 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9300000000-e468a2309943903fa596 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-cf7b4dbdb040a515988c | 2021-09-24 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 19993690 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 21126175 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB12271 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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