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Record Information
Version1.0
Creation Date2016-07-13 19:43:38 UTC
Update Date2016-09-23 18:44:48 UTC
LmdbLMDB00158
Secondary Accession NumbersNone
Metabolite Identification
Common NameAllantoin
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 animals, 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.
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
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
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
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
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 ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available