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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-09-11 01:14:48 UTC
NP-MRD IDNP0000012
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllantoin
DescriptionAllantoin, also known as glyoxyldiureide or 5-ureidohydantoin, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen. Allantoin is an extremely weak basic (essentially neutral) compound (based on its pKa). Allantoin exists in all living species, ranging from bacteria to humans. Outside of the human body, Allantoin is found, on average, in the highest concentration within milk (cow) and borages. Allantoin has also been detected, but not quantified in, several different foods, such as sour cherries, italian sweet red peppers, longans, sweet bay, and lambsquarters. This could make allantoin a potential biomarker for the consumption of these foods. Allantoin is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(2,5-Dioxo-4-imidazolidinyl)ureaChEBI
2,5-Dioxo-4-imidazolidinyl-ureaChEBI
4-Ureido-2,5-imidazolidinedioneChEBI
5-Ureido-2,4-imidazolidindioneChEBI
5-UreidohydantoinChEBI
GlyoxyldiureideChEBI
N-(2,5-Dioxo-4-imidazolidinyl)ureaChEBI
(S)-AllantoinHMDB
5-Ureido-hydantoinHMDB
5-UreidohydrantoinHMDB
AlantanHMDB
AllantolHMDB
AlloxantinHMDB
AVC/DienestrolcreamHMDB
CordianineHMDB
D00121HMDB
Fancol toinHMDB
GlyoxyldiureidHMDB
Glyoxylic diureideHMDB
PsoralonHMDB
SebicalHMDB
SeptalanHMDB
Sween brand OF allantoinHMDB
Herpecin-LHMDB
HerpecinLHMDB
Reed and carnrick brand OF allantoinHMDB
Woun'dresHMDB
Allantoin sween brandHMDB
Campbell brand OF allantoinHMDB
Allantoin campbell brandHMDB
Herpecin LHMDB
Chemical FormulaC4H6N4O3
Average Molecular Weight158.1154
Monoisotopic Molecular Weight158.043990078
IUPAC Name(2,5-dioxoimidazolidin-4-yl)urea
Traditional Nameallantoin
CAS Registry Number97-59-6
SMILES
NC(=O)NC1NC(=O)NC1=O
InChI Identifier
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)
InChI KeyPOJWUDADGALRAB-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR13C NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesEubacteria; Plantae
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Imidazole
  • Isourea
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point239 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.26 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.73 g/LALOGPS
logP-2ALOGPS
logP-2.4ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.02 m³·mol⁻¹ChemAxon
Polarizability12.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0000462
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001613
KNApSAcK IDC00007468
Chemspider ID199
KEGG Compound IDC01551
BioCyc IDALLANTOIN
BiGG IDNot Available
Wikipedia LinkAllantoin
METLIN ID89
PubChem Compound204
PDB IDNot Available
ChEBI ID15676
References
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [PubMed:11805243 ]
  3. Lagendijk J, Ubbink JB, Vermaak WJ: The determination of allantoin, a possible indicator of oxidant status, in human plasma. J Chromatogr Sci. 1995 Apr;33(4):186-93. [PubMed:7738135 ]
  4. Goldman SC, Holcenberg JS, Finklestein JZ, Hutchinson R, Kreissman S, Johnson FL, Tou C, Harvey E, Morris E, Cairo MS: A randomized comparison between rasburicase and allopurinol in children with lymphoma or leukemia at high risk for tumor lysis. Blood. 2001 May 15;97(10):2998-3003. [PubMed:11342423 ]
  5. Kand'ar R, Zakova P, Muzakova V: Monitoring of antioxidant properties of uric acid in humans for a consideration measuring of levels of allantoin in plasma by liquid chromatography. Clin Chim Acta. 2006 Mar;365(1-2):249-56. Epub 2005 Sep 27. [PubMed:16194528 ]
  6. Pavitt DV, de Fonseka S, Al-Khalaf N, Cam JM, Reaveley DA: Assay of serum allantoin in humans by gas chromatography-mass spectrometry. Clin Chim Acta. 2002 Apr;318(1-2):63-70. [PubMed:11880113 ]
  7. Alfazema LN, Howells S, Perrett D: Determination of allantoin in biofluids using micellar electrokinetic capillary chromatography. J Chromatogr A. 1998 Aug 21;817(1-2):345-52. [PubMed:9764504 ]
  8. Becker BF, Kastenbauer S, Kodel U, Kiesl D, Pfister HW: Urate oxidation in CSF and blood of patients with inflammatory disorders of the nervous system. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1201-4. [PubMed:15571231 ]
  9. Grootveld M, Halliwell B: Measurement of allantoin and uric acid in human body fluids. A potential index of free-radical reactions in vivo? Biochem J. 1987 May 1;243(3):803-8. [PubMed:3663100 ]