You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Allantoin (YMDB00213)

Identification
YMDB IDYMDB00213
NameAllantoin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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. Allantoin is an extremely weak basic (essentially neutral) compound (based on its pKa). Allantoin exists in all living species, ranging from bacteria to humans. Allantoin is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-allantoin
  • 2,5-Dioxo-4-imidazolidinyl-urea
  • 4-ureido-2,5-Imidazolidinedione
  • 5-ureido-Hydantoin
  • 5-Ureidohydantoin
  • 5-Ureidohydrantoin
  • Alantan
  • Allantoin
  • Allantol
  • Alloxantin
  • Cordianine
  • Glyoxyldiureid
  • Glyoxyldiureide
  • Glyoxylic diureide
  • N-(2,5-Dioxo-4-imidazolidinyl)urea
  • Psoralon
  • Sebical
  • Septalan
  • (2,5-Dioxo-4-imidazolidinyl)urea
  • 5-Ureido-2,4-imidazolidindione
  • AVC/Dienestrolcream
  • D00121
  • Fancol toin
  • Sween brand OF allantoin
  • Herpecin-L
  • HerpecinL
  • Reed and carnrick brand OF allantoin
  • Woun'dres
  • Allantoin sween brand
  • Campbell brand OF allantoin
  • Allantoin campbell brand
  • Herpecin L
CAS number97-59-6
WeightAverage: 158.1154
Monoisotopic: 158.043990078
InChI KeyPOJWUDADGALRAB-UHFFFAOYSA-N
InChIInChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
IUPAC Name(2,5-dioxoimidazolidin-4-yl)urea
Traditional IUPAC Nameallantoin
Chemical FormulaC4H6N4O3
SMILES[H]N([H])C(=O)N([H])C1([H])N([H])C(=O)N([H])C1=O
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
Charge0
Melting point239 °C
Experimental Properties
PropertyValueReference
Water Solubility5.26 mg/mL [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogPNot AvailablePhysProp
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
water + Allantoin ↔ Allantoic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
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-d6d990e16a15b9f27262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0920000000-abb5512bfc08cbdd004fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f79-0900000000-bf39d4fc494ccd722796JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kr-4911230000-f2112ac79e45fb821ab6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f8i-3933100000-45367e01790bfc8afd6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfr-4951100000-88808e71aea4d5ad7885JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-5f4cd23ea44234e5a455JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c9c0d8a7f1e5f105a9c3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uds-0911000000-d6d990e16a15b9f27262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-bf39d4fc494ccd722796JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kr-4911230000-f2112ac79e45fb821ab6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f8i-3933100000-45367e01790bfc8afd6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfr-4951100000-88808e71aea4d5ad7885JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9700000000-45ea72c639ca30cd7783JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02t9-8900000000-bb0a5fee22239a104e6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dj-9000000000-09992debd5f3d399b902JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01oy-9000000000-8fe7df22b2abb81b934aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9100000000-08b1881abaf98821d201JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0006-9100000000-297710f62f9699946151JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0900000000-4e30eec1c2a8c4cb7fa8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5900000000-0e0e6cbea70e14292a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9000000000-d53fc563af9567f05b8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4c973a5209a8104a49e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-9600000000-775f532f9c5d9acd1ee6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-9400000000-a4e69e926b530e953cc3JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-5ad052308edfab7b8c5fJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Lawther, R. P., Riemer, E., Chojnacki, B., Cooper, T. G. (1974). "Clustering of the genes for allantoin degradation in Saccharomyces cerevisiae." J Bacteriol 119:461-468.4604238
Synthesis Reference:Du, Niansheng; Yang, Jianhua; Rena, Kasimu. Method for isolation of allantoin from Cistanche deserticola. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 5pp.
External Links:
ResourceLink
CHEBI ID15676
HMDB IDHMDB00462
Pubchem Compound ID204
Kegg IDC01551
ChemSpider ID199
FOODB IDFDB001613
WikipediaAllantoin
BioCyc IDR--ALLANTOIN

Enzymes

Protein Details
1. Allantoinase
General function:
Involved in allantoinase activity
Specific function:
Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:
DAL1
Uniprot ID:
P32375
Molecular weight:
50125.89844
Reactions
(S)-allantoin + H(2)O → allantoate.

Transporters

Protein Details
1. Allantoin permease
General function:
Involved in nucleobase transmembrane transporter activity
Specific function:
Transport of allantoin
Gene Name:
DAL4
Uniprot ID:
Q04895
Molecular weight:
71755.5