Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Allantoic acid (M2MDB000299)

Record Information
Version2.0
Creation Date2012-05-31 13:47:43 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01209
Identification
Name:Allantoic acid
DescriptionAllantoic acid is the END product of Allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation (Purine metabolism). It is a crystalline acid obtained by hydrolysis of allantoin. (Wikipedia)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Allantoate
  • Allantoic acid
  • Diureidoacetate
  • Diureidoacetic acid
Chemical Formula:C4H8N4O4
Weight:Average: 176.1307
Monoisotopic: 176.054554764
InChI Key:NUCLJNSWZCHRKL-UHFFFAOYSA-N
InChI:InChI=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)
CAS number:99-16-1
IUPAC Name:2,2-bis(carbamoylamino)acetic acid
Traditional IUPAC Name:allantoic acid
SMILES:NC(=O)NC(NC(N)=O)C(O)=O
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
State:Solid
Charge:-1
Melting point:180-181 °C
Experimental Properties:
PropertyValueSource
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
Reactions:
Allantoin + Water > Allantoic acid + Hydrogen ion
Allantoic acid + 2 Hydrogen ion + 2 Water > Carbon dioxide +2 Ammonium + (S)-Ureidoglycolic acid
Allantoic acid + Water <> Ureidoglycine + Ammonia + Carbon dioxide
(S)(+)-Allantoin + Water <> Allantoic acid
Hydrogen ion + Allantoic acid + Water > <i>S</i>-ureidoglycine + Ammonia + Carbon dioxide
<i>S</i>-allantoin + Water > Hydrogen ion + Allantoic acid
(S)(+)-Allantoin + Water > Allantoic acid
Allantoic acid + Water + 2 Hydrogen ion > Carbon dioxide + Ammonium + S-ureidoglycine
SMPDB Pathways:
allantoin degradation (anaerobic)PW002050 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolate and glyoxylate degradationPW000827 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • allantoin degradation to ureidoglycolate II (ammonia producing) PWY-5698
Concentrations
Not 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)splash10-0002-1900000000-21581f2d921374c16317View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uej-0911000000-7b31dde6fb9c6e9ac110View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7a-0900000000-d8f1371697a09dc2d063View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-7557e41727738c553aefView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9800000000-0da9967a35111f5e77c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9320000000-3e52483917d7449c6f21View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9500000000-311fe8e2669139e60084View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03k9-9000000000-eb594a4f54a39f5aaad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-24cb204bd4d824cf2b53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-003r-0900000000-91ad7fef4b504549f849View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-6f90d802bf75ec4bc187View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00dr-9000000000-3900e78a2acf61f39effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00dl-9000000000-e98594c1e1b2aa50540aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-003r-0900000000-91ad7fef4b504549f849View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-1f86fa2bb6e6a3e1988eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-6f90d802bf75ec4bc187View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dr-9000000000-3900e78a2acf61f39effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-9000000000-e98594c1e1b2aa50540aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-c2a7cae004d98357168aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-9000000000-31fc32546236ce67c00cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-27a2a739677caaa22b0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9400000000-120384794acaedafde99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-bf94440d44163d36a2e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004r-9500000000-f32dafebab7d351734b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-1900000000-e1f2f46a56a37aa06912View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-9600000000-ee4b95c0d08c896e3843View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9300000000-1beb69c57c7dfcea4351View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-682ec8d4340d0075c369View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-9400000000-6faaacd64e9faecfb1bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ac2cde105e2954f49b46View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vigetti D, Pollegioni L, Monetti C, Prati M, Bernardini G, Gornati R: Property comparison of recombinant amphibian and mammalian allantoicases. FEBS Lett. 2002 Feb 13;512(1-3):323-8. Pubmed: 11852104
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Hermanowicz, Witold. Allantoic acid. Formation of allantoic acid from allantoin. Roczniki Chemii (1948), 22 159-80.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID30837
HMDB IDHMDB01209
Pubchem Compound ID203
Kegg IDC00499
ChemSpider ID198
Wikipedia IDAllantoic_acid
BioCyc IDALLANTOATE
EcoCyc IDALLANTOATE
Ligand Expo1AL

Enzymes

Protein Details
1. Allantoate amidohydrolase
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Involved in the anaerobic utilization of allantoin. Converts allantoate to (S)-ureidoglycolate and ammonia
Gene Name:
allC
Uniprot ID:
P77425
Molecular weight:
45694
Protein Details
2. Allantoinase
General function:
Involved in allantoinase activity
Specific function:
Catalyzes the conversion of allantoin (5- ureidohydantoin) to allantoic acid by hydrolytic cleavage of the five-member hydantoin ring
Gene Name:
allB
Uniprot ID:
P77671
Molecular weight:
49601
Reactions
(S)-allantoin + H(2)O = allantoate.