Record Information
Version2.0
Creation Date2012-05-31 14:23:09 -0600
Update Date2015-06-03 17:19:08 -0600
Secondary Accession Numbers
  • ECMDB20018
Identification
Name:(S)(+)-Allantoin
DescriptionAllantoin 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).
Structure
Thumb
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
Chemical Formula:C4H6N4O3
Weight:Average: 158.1154
Monoisotopic: 158.043990078
InChI Key:POJWUDADGALRAB-SFOWXEAESA-N
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
CAS number:97-59-6
IUPAC Name:N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid
Traditional IUPAC Name:N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid
SMILES:[H][C@]1(NC(O)=N)N=C(O)N=C1O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentAllantoins
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:239 °C
Experimental Properties:
PropertyValueSource
Water Solubility:5.26 mg/mL [YALKOWSKY,SH & HE,Y (2003)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP-1.5ALOGPS
logP-1.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)5.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area121.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44 m³·mol⁻¹ChemAxon
Polarizability13.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1900000000-7bd13f672c17d120b1c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-6900000000-86d834317b3cea626f53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-e616e553f12597e80e35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-a0c5667d9df61e3f5114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9300000000-41072b8960aef6569b10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a84520a275e715df81edView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15678
HMDB IDNot Available
Pubchem Compound ID204
Kegg IDC02350
ChemSpider ID388780
Wikipedia IDNot Available
BioCyc IDALLANTOIN
EcoCyc IDALLANTOIN
Ligand Expo3AL

Enzymes

General function:
Involved in allantoinase activity
Specific function:
Catalyzes the conversion of allantoin (5- ureidohydantoin) to allantoic acid by hydrolytic cleavage of the five-member hydantoin ring
Gene Name:
allB
Uniprot ID:
P77671
Molecular weight:
49601
Reactions
(S)-allantoin + H(2)O = allantoate.