| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-05-31 14:23:09 -0600 |
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| Update Date | 2015-06-03 17:19:08 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | (S)(+)-Allantoin |
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| Description | Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a diureide of glyoxylic acid. (Wikipedia) In E. coli K-12, the enzyme allantoinase (EC 3.5.2.5) catalyzes the conversion of (S)(+)-Allantoin to Allantoate (KEGG). |
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| Structure | |
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| Synonyms: | - (+/-)-allantoin
- (2,5-dioxo-4-imidazolidinyl)-Urea
- (2,5-Dioxo-4-imidazolidinyl)urea
- (S)-allantoin
- 1-(2,5-Dioxoimidazolidin-4-yl)urea
- 2,5-Dioxo-4-imidazolidinyl-urea
- 4-Ureido-2,5-Imidazolidinedione
- 5-Ureido-2,4-imidazolidindion
- 5-Ureido-Hydantoin
- 5-Ureidohydantoin
- 5-Ureidohydrantoin
- Alantan
- Allantoin
- Allantoin (8CI)
- Allantoin (jan/usp)
- Allantoin [usan:ban]
- Allantol
- Alloxantin
- Avc/dienestrolcream
- Cordianine
- Cutemol emollient
- DL-allantoin
- Fancol toin
- Glyoxyldiureid
- Glyoxyldiureide
- Glyoxylic diureide
- Glyoxylic(acid) diureide
- Hemocane
- N-(2,5-Dioxo-4-imidazolidinyl)urea
- N-(2,5-Dioxoimidazolidin-4-yl)urea
- N-[2,5-Dioxoimidazolidin-4-yl]urea
- Paxyl
- Prestwick_11
- Psoralon
- Sebical
- Septalan
- Uniderm a
- Urea, (2,5-dioxo-4-imidazolidinyl)- (9CI)
- Ureidohydantoin
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| Chemical Formula: | C4H6N4O3 |
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| Weight: | Average: 158.1154
Monoisotopic: 158.043990078 |
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| InChI Key: | POJWUDADGALRAB-SFOWXEAESA-N |
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| InChI: | InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1 |
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| CAS number: | 97-59-6 |
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| IUPAC Name: | N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid |
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| Traditional IUPAC Name: | N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid |
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| SMILES: | [H][C@]1(NC(O)=N)N=C(O)N=C1O |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as allantoins. These are heterocyclic compounds containing an imiazolidine ring substituted by a ketone group at positions 2 and 5, and an urea at position 4. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Azolidines |
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| Sub Class | Imidazolidines |
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| Direct Parent | Allantoins |
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| Alternative Parents | |
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| Substituents | - Allantoin
- Alpha-amino acid or derivatives
- 5-monosubstituted hydantoin
- N-acyl urea
- Ureide
- Dicarboximide
- Carbonic acid derivative
- Urea
- Carboxylic acid derivative
- Azacycle
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State: | Solid |
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| Charge: | -1 |
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| Melting point: | 239 °C |
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| Experimental Properties: | | Property | Value | Source |
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| Water Solubility: | 5.26 mg/mL [YALKOWSKY,SH & HE,Y (2003)] | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Cytoplasm |
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| Reactions: | |
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| SMPDB Pathways: | Not Available |
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| KEGG Pathways: | |
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| EcoCyc Pathways: | Not Available |
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| Concentrations |
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| Not Available |
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| Spectra |
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| Spectra: | |
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| References |
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| References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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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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