Record Information
Version1.0
Creation date2010-04-08 22:05:02 UTC
Update date2015-10-09 22:27:50 UTC
Primary IDFDB001613
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAllantoin
DescriptionAllantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Named after the allantois, an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and higher apes, it is a product of oxidation of uric acid by purine catabolism. After birth, it is the predominant means by which nitrogenous waste is excreted in the urine of these animals. In humans and higher apes, the metabolic pathway for conversion of uric acid to allantoin is not present, so the former is excreted. Recombinant rasburicase is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ammonia) before excretion. Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.; Its chemical formula is 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. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. Allantoin is a botanical extract of the comfrey plant and is used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulate growth of healthy tissue. This extract 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.
CAS Number97-59-6
Structure
Thumb
Synonyms
SynonymSource
(+/-)-allantoinbiospider
(2,5-Dioxo-4-imidazolidinyl)ureabiospider
1-(2,5-dioxoimidazolidin-4-yl)ureabiospider
2,5-Dioxo-4-imidazolidinyl-ureabiospider
2,5-Imidazolidinedione, 4-ureido-biospider
4-ureido-2,5-Imidazolidinedionebiospider
5-Ureido-2,4-imidazolidindionbiospider
5-ureido-Hydantoinbiospider
5-Ureidohydantoinbiospider
5-Ureidohydrantoinbiospider
Alantanbiospider
Allantoin (8CI)biospider
Allantoin (jan/usp)biospider
Allantoin [usan:ban]biospider
Allantoin campbell brandbiospider
Allantoin sween brandbiospider
Allantolbiospider
Alloxantinbiospider
Campbell brand of allantoinbiospider
Cordianinebiospider
Cutemol emollientbiospider
DL-allantoinbiospider
Fancol toinbiospider
Glyoxyldiureidbiospider
Glyoxyldiureidebiospider
Glyoxylic diureidebiospider
Glyoxylic(acid) diureidebiospider
Hemocanebiospider
Herpecin lbiospider
Herpecin-lbiospider
Herpecinlbiospider
Hydantoin, 5-ureido-biospider
N-(2,5-Dioxo-4-imidazolidinyl)ureabiospider
N-(2,5-dioxoimidazolidin-4-yl)ureabiospider
N-[2,5-dioxoimidazolidin-4-yl]ureabiospider
Paxylbiospider
Psoralonbiospider
Reed & carnrick brand of allantoinbiospider
Sebicalbiospider
Septalanbiospider
Skin strategies for men-soothing moisturizerbiospider
Sween brand of allantoinbiospider
Uniderm abiospider
Urea, (2, 5-dioxo-4-imidazolidinyl)-biospider
Urea, (2,5-dioxo-4-imidazolidinyl)-biospider
Urea, (2,5-dioxo-4-imidazolidinyl)- (9CI)biospider
Urea, N-(2,5-dioxo-4-imidazolidinyl)-biospider
Ureidohydantoinbiospider
Woun'dresbiospider
Predicted Properties
PropertyValueSource
Water Solubility4.73 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.02 m³·mol⁻¹ChemAxon
Polarizability12.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6N4O3
IUPAC name(2,5-dioxoimidazolidin-4-yl)urea
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 KeyInChIKey=POJWUDADGALRAB-UHFFFAOYSA-N
Isomeric SMILESNC(=O)NC1NC(=O)NC1=O
Average Molecular Weight158
Monoisotopic Molecular Weight158
Classification
DescriptionThis compound belongs to the class of organic compounds known as imidazoles. These 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point239 oC
Boiling PointNot Available
Experimental Water Solubility5.26 mg/mLYALKOWSKY,SH & HE,Y (2003)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uds-0911000000-d6d990e16a15b9f27262View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0920000000-abb5512bfc08cbdd004fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-5f4cd23ea44234e5a455View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uds-0911000000-d6d990e16a15b9f27262View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-bf39d4fc494ccd722796View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-4911230000-f2112ac79e45fb821ab6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f8i-3933100000-45367e01790bfc8afd6eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfr-4951100000-88808e71aea4d5ad7885View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9700000000-45ea72c639ca30cd7783View 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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01551
Pubchem Compound ID204
Pubchem Substance IDNot Available
ChEBI ID15676
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00462
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDALLANTOIN
BIGG IDNot Available
KNApSAcK IDC00007468
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAllantoin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti dandruffDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti pepticDUKE
anti psoriac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti radicularDUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
keratolyticDUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
suppurativeDUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.