Allantoin (CHEM003892)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-09-11 05:23:11 UTC
Update Date2026-03-31 17:33:06 UTC
Accession NumberCHEM003892
Identification
Common NameAllantoin
ClassSmall Molecule
DescriptionAllantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard Allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as shampoos, lipsticks, various cosmetic lotions and creams and other cosmetic and pharmaceutical products.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Animal Toxin
  • Cosmetic Toxin
  • Food Toxin
  • Household Toxin
  • Mammal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass158.115 g/mol
Monoisotopic Mass158.044 g/mol
CAS Registry Number97-59-6
IUPAC Name(2,5-dioxoimidazolidin-4-yl)urea
Traditional Nameallantoin
SMILESNC(=O)NC1NC(=O)NC1=O
InChI IdentifierInChI=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
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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point239 °C
Boiling PointNot Available
Solubility5.26 mg/mL
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uds-0911000000-d6d990e16a15b9f27262Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0920000000-abb5512bfc08cbdd004fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f79-0900000000-bf39d4fc494ccd722796Spectrum
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kr-4911230000-f2112ac79e45fb821ab6Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f8i-3933100000-45367e01790bfc8afd6eSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfr-4951100000-88808e71aea4d5ad7885Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-5f4cd23ea44234e5a455Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uds-0911000000-d6d990e16a15b9f27262Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-bf39d4fc494ccd722796Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-4911230000-f2112ac79e45fb821ab6Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f8i-3933100000-45367e01790bfc8afd6eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfr-4951100000-88808e71aea4d5ad7885Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9700000000-45ea72c639ca30cd7783Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02t9-8900000000-bb0a5fee22239a104e6fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dj-9000000000-09992debd5f3d399b902Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01oy-9000000000-8fe7df22b2abb81b934aSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9100000000-08b1881abaf98821d201Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0006-9100000000-297710f62f9699946151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-5ad052308edfab7b8c5fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000462
FooDB IDFDB001613
Phenol Explorer IDNot Available
KNApSAcK IDC00007468
BiGG IDNot Available
BioCyc IDALLANTOIN
METLIN ID89
PDB IDNot Available
Wikipedia LinkAllantoin
Chemspider ID199
ChEBI ID15676
PubChem Compound ID204
Kegg Compound IDC01551
YMDB IDYMDB00213
ECMDB IDECMDB00462
References
Synthesis ReferenceDu, Niansheng; Yang, Jianhua; Rena, Kasimu. Method for isolation of allantoin from Cistanche deserticola. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 5pp.
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11157020
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14619112
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190852
4. Du, Niansheng; Yang, Jianhua; Rena, Kasimu. Method for isolation of allantoin from Cistanche deserticola. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 5pp.
5. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.
6. Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0.
7. Du, Niansheng; Yang, Jianhua; Rena, Kasimu. Method for isolation of allantoin from Cistanche deserticola. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 5pp.
8. 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.
9. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. Goelzer A, Bekkal Brikci F, Martin-Verstraete I, Noirot P, Bessieres P, Aymerich S, Fromion V: Reconstruction and analysis of the genetic and metabolic regulatory networks of the central metabolism of Bacillus subtilis. BMC Syst Biol. 2008 Feb 26;2:20. doi: 10.1186/1752-0509-2-20.
18. Navone L, Casati P, Licona-Cassani C, Marcellin E, Nielsen LK, Rodriguez E, Gramajo H: Allantoin catabolism influences the production of antibiotics in Streptomyces coelicolor. Appl Microbiol Biotechnol. 2014 Jan;98(1):351-60. doi: 10.1007/s00253-013-5372-1. Epub 2013 Nov 29.
19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.