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Identification
YMDB IDYMDB00199
NameAllantoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAllantoate is an intermediate in the allantoin degradation to glyoxylate pathway. It is the end product of allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation in the purine metabolism. Allantoin is rich in nitrogen, and many organisms are able to degrade it and recycle it. Yeast can use allantoin as sole nitrogen source by degrading it to urea, CO2 and glyoxylate. Urea is further degraded to ammonia. [Biocyc PWY-5694]
Structure
Thumb
Synonyms
  • Allantoate
  • Allantoic acid
  • bis[(aminocarbonyl)amino]acetate
  • Diureidoacetate
  • Diureidoacetic acid
  • Bis[(aminocarbonyl)amino]acetic acid
  • Allantoic acid, monosodium salt
CAS number99-16-1
WeightAverage: 176.1307
Monoisotopic: 176.054554764
InChI KeyNUCLJNSWZCHRKL-UHFFFAOYSA-N
InChIInChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)
IUPAC Name2,2-bis(carbamoylamino)acetic acid
Traditional IUPAC Nameallantoic acid
Chemical FormulaC4H8N4O4
SMILES[H]OC(=O)C([H])(N([H])C(=O)N([H])[H])N([H])C(=O)N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-carbamoyl-alpha amino acids
Alternative Parents
Substituents
  • N-carbamoyl-alpha-amino acid
  • Urea
  • Carbonic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point180-181 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.7 g/LALOGPS
logP-2.1ALOGPS
logP-2.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area147.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.1 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
Allantoic acid + waterUrea + Ureidoglycolic acid
water + AllantoinAllantoic 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)splash10-0002-1900000000-21581f2d921374c16317JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uej-0911000000-7b31dde6fb9c6e9ac110JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7a-0900000000-d8f1371697a09dc2d063JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-7557e41727738c553aefJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9800000000-0da9967a35111f5e77c5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9320000000-3e52483917d7449c6f21JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9500000000-311fe8e2669139e60084JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-9000000000-eb594a4f54a39f5aaad4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-24cb204bd4d824cf2b53JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-003r-0900000000-91ad7fef4b504549f849JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-6f90d802bf75ec4bc187JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00dr-9000000000-3900e78a2acf61f39effJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00dl-9000000000-e98594c1e1b2aa50540aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003r-0900000000-91ad7fef4b504549f849JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-6f90d802bf75ec4bc187JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-9000000000-3900e78a2acf61f39effJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-e98594c1e1b2aa50540aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-1900000000-e1f2f46a56a37aa06912JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-9600000000-ee4b95c0d08c896e3843JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9300000000-1beb69c57c7dfcea4351JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-682ec8d4340d0075c369JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-9400000000-6faaacd64e9faecfb1bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ac2cde105e2954f49b46JSpectraViewer
1D NMR1H 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:Hermanowicz, Witold. Allantoic acid. Formation of allantoic acid from allantoin. Roczniki Chemii (1948), 22 159-80.
External Links:
ResourceLink
CHEBI ID30837
HMDB IDHMDB01209
Pubchem Compound ID203
Kegg IDC00499
ChemSpider ID198
FOODB IDFDB012646
WikipediaAllantoic_acid
BioCyc IDALLANTOATE

Enzymes

General function:
Involved in allantoicase activity
Specific function:
Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:
DAL2
Uniprot ID:
P25335
Molecular weight:
38713.5
Reactions
Allantoate + H(2)O → (S)-ureidoglycolate + urea.
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

General function:
Involved in transporter activity
Specific function:
Component of the allantoate transport system
Gene Name:
DAL5
Uniprot ID:
P15365
Molecular weight:
60849.5