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Record Information
Version2.0
Creation Date2014-09-11 05:23:11 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4936
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.
Compound Type
  • Amide
  • Amine
  • Animal Toxin
  • Cosmetic Toxin
  • Food Toxin
  • Household Toxin
  • Mammal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(S)-allantoin
2,5-Dioxo-4-imidazolidinyl-urea
4-Ureido-2,5-Imidazolidinedione
5-Ureido-Hydantoin
5-Ureidohydantoin
5-Ureidohydrantoin
Alantan
Allantol
Alloxantin
AVC/Dienestrolcream
Cordianine
D00121
Fancol TOIN
Glyoxyldiureid
Glyoxyldiureide
Glyoxylic diureide
N-(2,5-Dioxo-4-imidazolidinyl)urea
Psoralon
Sebical
Septalan
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
SMILESOC(=N)NC1N=C(O)N=C1O
InChI IdentifierInChI=1/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
InChI KeyInChIKey=POJWUDADGALRAB-UHFFFAOYNA-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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.73 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.4ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.02 m3·mol-1ChemAxon
Polarizability12.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0uds-0911000000-d6d990e16a15b9f27262View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0920000000-abb5512bfc08cbdd004fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0f79-0900000000-bf39d4fc494ccd722796View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kr-4911230000-f2112ac79e45fb821ab6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f8i-3933100000-45367e01790bfc8afd6eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfr-4951100000-88808e71aea4d5ad7885View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0296-9700000000-45ea72c639ca30cd7783View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9100000000-5f4cd23ea44234e5a455View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9100000000-c9c0d8a7f1e5f105a9c3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0uds-0911000000-d6d990e16a15b9f27262View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f79-0900000000-bf39d4fc494ccd722796View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00kr-4911230000-f2112ac79e45fb821ab6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0f8i-3933100000-45367e01790bfc8afd6eView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0zfr-4951100000-88808e71aea4d5ad7885View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02t9-8900000000-bb0a5fee22239a104e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dj-9000000000-09992debd5f3d399b902View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01oy-9000000000-8fe7df22b2abb81b934aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9100000000-08b1881abaf98821d201View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0006-9100000000-297710f62f9699946151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-5ad052308edfab7b8c5fView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00462
PubChem Compound ID204
ChEMBL IDNot Available
ChemSpider ID199
KEGG IDC01551
UniProt IDNot Available
OMIM ID
ChEBI ID15676
BioCyc IDR--ALLANTOIN
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkAllantoin
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. Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [11805243 ]
  2. 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. [12829005 ]
  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. [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. [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. [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. [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. [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. [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. [3663100 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.92 uMATG_PXR_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.22 uMATG_PPARa_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]