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allantoic acid

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CAS Number: 99-16-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:202-735-4
FDA UNII: 02WGT7SHWJ
Nikkaji Web:J11.619J
MDL:MFCD00007949
XlogP3-AA:-2.60 (est)
Molecular Weight:176.13256000
Formula:C4 H8 N4 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
allantoic acid free acid
Odor: characteristic
Use: An metabolic intermediate in nucleic acid metabolism.
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for allantoic acid usage levels up to:
 not for fragrance use.
 
Recommendation for allantoic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):99-16-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :203
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,2-bis(carbamoylamino)acetic acid
Chemidplus:0000099161
 
References:
 2,2-bis(carbamoylamino)acetic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):203
Pubchem (cas):99-16-1
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C00499
HMDB (The Human Metabolome Database):HMDB01209
FooDB:FDB012646
YMDB (Yeast Metabolome Database):YMDB00199
Export Tariff Code:2924.10.1050
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean black bean fruit
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 bean field bean fruit
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 coffee bean
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 coffee leaf
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 hazelnut leaf
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 lupine white lupine sprout
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 soybean leaf
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 tea plant
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Synonyms:
 acetic acid, bis((aminocarbonyl)amino)-
bis((aminocarbonyl)amino)acetic acid
2,2-bis(carbamoylamino)acetic acid
 diureidoacetic acid
 

Articles:

PubMed:Therapeutic efficacy of atypical antipsychotic drugs by targeting multiple stress-related metabolic pathways.
PubMed:Increasing Nitrogen Fixation and Seed Development in Soybean Requires Complex Adjustments of Nodule Nitrogen Metabolism and Partitioning Processes.
PubMed:Allantoin accumulation mediated by allantoinase downregulation and transport by Ureide Permease 5 confers salt stress tolerance to Arabidopsis plants.
PubMed:Early signaling, synthesis, transport and metabolism of ureides.
PubMed:Chronical sleep interruption-induced cognitive decline assessed by a metabolomics method.
PubMed:AllR Controls the Expression of Streptomyces coelicolor Allantoin Pathway Genes.
PubMed:Short-term effect of caffeine on purine, pyrimidine and pyridine metabolism in rice (Oryza sativa) seedlings.
PubMed:Structural insights into the substrate specificity of (s)-ureidoglycolate amidohydrolase and its comparison with allantoate amidohydrolase.
PubMed:Transporters involved in source to sink partitioning of amino acids and ureides: opportunities for crop improvement.
PubMed:Molecular and functional characterization of allantoate amidohydrolase from Phaseolus vulgaris.
PubMed:Gene context analysis reveals functional divergence between hypothetically equivalent enzymes of the purine-ureide pathway.
PubMed:Biochemical and mutational studies of allantoinase from Bacillus licheniformis CECT 20T.
PubMed:The ureide-degrading reactions of purine ring catabolism employ three amidohydrolases and one aminohydrolase in Arabidopsis, soybean, and rice.
PubMed:Metabolic fate of 14C-labelled nicotinamide and adenine in germinating propagules of the mangrove Bruguiera gymnorrhiza.
PubMed:Soybean ureide transporters play a critical role in nodule development, function and nitrogen export.
PubMed:Polar compounds isolated from the leaves of Albertisia delagoensis (Menispermaceae).
PubMed:Transcriptional regulation of the gene cluster encoding allantoinase and guanine deaminase in Klebsiella pneumoniae.
PubMed:Development of microsphere-based multiplex branched DNA assay for detection and differentiation of avian influenza virus strains.
PubMed:A metabolomics approach using juvenile cystic mice to identify urinary biomarkers and altered pathways in polycystic kidney disease.
PubMed:Ureide metabolism during seedling development in French bean (Phaseolus vulgaris).
PubMed:Purine utilization by Klebsiella oxytoca M5al: genes for ring-oxidizing and -opening enzymes.
PubMed:A critical role for ureides in dark and senescence-induced purine remobilization is unmasked in the Atxdh1 Arabidopsis mutant.
PubMed:Tissue abundance and characterization of two purified proteins with allantoinase activity from French bean (Phaseolus vulgaris).
PubMed:Discovery of an alternate metabolic pathway for urea synthesis in adult Aedes aegypti mosquitoes.
PubMed:Biochemical characterisation of an allantoate-degrading enzyme from French bean (Phaseolus vulgaris): the requirement of phenylhydrazine.
PubMed:Uric acid recycling in the shield bug, Parastrachia japonensis (Hemiptera: Parastrachiidae), during diapause.
PubMed:Allantoin has a limited role as nitrogen source in cultured coffee cells.
PubMed:Nickel deficiency disrupts metabolism of ureides, amino acids, and organic acids of young pecan foliage.
PubMed:Control of hyperuricemia in subjects with refractory gout, and induction of antibody against poly(ethylene glycol) (PEG), in a phase I trial of subcutaneous PEGylated urate oxidase.
PubMed:Update on ureide degradation in legumes.
PubMed:Inhibition of N2 fixation in soybean is associated with elevated ureides and amino acids.
PubMed:Biosynthesis, accumulation and degradation of theobromine in developing Theobroma cacao fruits.
PubMed:Soybean cultivars 'Williams 82' and 'Maple Arrow' produce both urea and ammonia during ureide degradation.
PubMed:Ureide biosynthesis in legume nodules.
PubMed:Catabolism of caffeine in plants and microorganisms.
PubMed:Insect allantoinase: cDNA cloning, purification, and characterization of the native protein from the cat flea, Ctenocephalides felis.
PubMed:PvUPS1, an allantoin transporter in nodulated roots of French bean.
PubMed:Purine degradation in the edible mushroom Agaricus bisporus.
PubMed:Metal ion dependence of recombinant Escherichia coli allantoinase.
PubMed:Roles of PucR, GlnR, and TnrA in regulating expression of the Bacillus subtilis ure P3 promoter.
PubMed:[Studies on chemical constituents of seeds of Desmos chinensis Lour].
PubMed:Allantoin as a free-radical scavenger.
PubMed:Property comparison of recombinant amphibian and mammalian allantoicases.
PubMed:The purine degradation pathway: possible role in paralytic shellfish toxin metabolism in the cyanobacterium Planktothrix sp. FP1.
PubMed:Functional analysis of 14 genes that constitute the purine catabolic pathway in Bacillus subtilis and evidence for a novel regulon controlled by the PucR transcription activator.
PubMed:Leaf ureide degradation and N(2) fixation tolerance to water deficit in soybean.
PubMed:Bacillus subtilis guanine deaminase is encoded by the yknA gene and is induced during growth with purines as the nitrogen source.
PubMed:Functional expression and characterization of the two cyclic amidohydrolase enzymes, allantoinase and a novel phenylhydantoinase, from Escherichia coli.
PubMed:Ureide degradation pathways in intact soybean leaves.
PubMed:Biosynthesis and catabolism of caffeine in low-caffeine-containing species of Coffea.
PubMed:Xanthine degradation and related enzyme activities in leaves and fruits of two coffea species differing in caffeine catabolism.
PubMed:Assays for allantoinase.
PubMed:Allantoin and allantoic acid titre in the faeces and tissues of the developing larva of the moth, Orthaga exvinacea Hampson.
PubMed:Theophylline metabolism in higher plants.
PubMed:Urease Is Not Essential for Ureide Degradation in Soybean.
PubMed:Biotoxic effects of copper on ureide metabolism of pigeon pea.
PubMed:Immunoaffinity purification and comparison of allantoinases from soybean root nodules and cotyledons.
PubMed:The level of enzymes involved in the allantoin metabolism of Bacillus fastidiosus grown under different conditions.
PubMed:Proposed physiologic functions of boron in plants pertinent to animal and human metabolism.
PubMed:Amphibian allantoinase. Molecular cloning, tissue distribution, and functional expression.
PubMed:Purification of allantoinase from soybean seeds and production and characterization of anti-allantoinase antibodies.
PubMed:[Stability of allantoin and identification of its degradation compounds].
PubMed:N-carbamoyl-D-amino acid amidohydrolase from Comamonas sp. E222c purification and characterization.
PubMed:Catabolism of adenine nucleotides in suspension-cultured plant cells.
PubMed:Distribution and metabolism of xylem-borne ureido and amino compounds in developing soybean shoots.
PubMed:Effect of oxygen pressure on synthesis and export of nitrogenous solutes by nodules of cowpea.
PubMed:Ureide assay for measuring nitrogen fixation by nodulated soybean calibrated by N methods.
PubMed:A high-performance liquid chromatography method for separation of purine bases, nucleosides and ureides: application to studies on purine catabolism in higher plants.
PubMed:Appearance of purine-catabolizing enzymes in fix and fix root nodules on soybean and effect of oxygen on the expression of the enzymes in callus tissue.
PubMed:Transcriptional regulation of the DAL5 gene in Saccharomyces cerevisiae.
PubMed:Ureidosuccinate is transported by the allantoate transport system in Saccharomyces cerevisiae.
PubMed:Regulation of allantoate transport in wild-type and mutant strains of Saccharomyces cerevisiae.
PubMed:Two indirect methods for detecting ureide synthesis by nodulated legumes.
PubMed:Structure and possible ureide degrading function of the ubiquitous urease of soybean.
PubMed:The all2 gene is required for the induction of the purine deamination pathway in Schizosaccharomyces pombe.
PubMed:Purification and properties of inosine monophosphate oxidoreductase from nitrogen-fixing nodules of cowpea (Vigna unguiculata L. Walp).
PubMed:Nitrogen nutrition and the development of biochemical functions associated with nitrogen fixation and ammonia assimilation of nodules on cowpea seedlings.
PubMed:Purine synthesis and catabolism in soybean seedlings : the biogenesis of ureides.
PubMed:Concentrations of sucrose and nitrogenous compounds in the apoplast of developing soybean seed coats and embryos.
PubMed:5-Phosphoribosylpyrophosphate amidotransferase from soybean root nodules: kinetic and regulatory properties.
PubMed:Genetic studies of purine breakdown in the fission yeast Schizosaccharomyces pombe.
PubMed:Role of amides, amino acids, and ureides in the nutrition of developing soybean seeds.
PubMed:Allantoin degradation by Saccharomyces cerevisiae--a model system for gene regulation and metabolic integration.
PubMed:Autoanalytical procedure for the determination of allantoin and allantoic Acid in soybean tissue.
PubMed:Cellular and subcellular organization of pathways of ammonia assimilation and ureide synthesis in nodules of cowpea (Vigna unguiculata L. Walp.).
PubMed:Mössbauer and EPR study of the binuclear iron centre in purple acid phosphatase.
PubMed:Enzymes of ureide synthesis in pea and soybean.
PubMed:Isolation and characterization of mutants that produce the allantoin-degrading enzymes constitutively in Saccharomyces cerevisiae.
PubMed:Metabolism and translocation of allantoin in ureide-producing grain legumes.
PubMed:N abundance of nodules as an indicator of N metabolism in n(2)-fixing plants.
PubMed:Enzymes of amide and ureide biogenesis in developing soybean nodules.
PubMed:Ion balance, uptake, and transport processes in n(2)-fixing and nitrate- and urea-dependent soybean plants.
PubMed:Enzymes of Purine Biosynthesis and Catabolism in Glycine max: I. COMPARISON OF ACTIVITIES WITH N(2) FIXATION AND COMPOSITION OF XYLEM EXUDATE DURING NODULE DEVELOPMENT.
PubMed:Localization of enzymes of ureide biosynthesis in peroxisomes and microsomes of nodules.
PubMed:Uninfected cells of soybean root nodules: ultrastructure suggests key role in ureide production.
PubMed:The Assimilation of Ureides in Shoot Tissues of Soybeans : 1. CHANGES IN ALLANTOINASE ACTIVITY AND UREIDE CONTENTS OF LEAVES AND FRUITS.
PubMed:Biosynthesis of Ureides from Purines in a Cell-free System from Nodule Extracts of Cowpea [Vigna unguiculata (L) Walp.].
PubMed:Allantoic Acid Synthesis in Soybean Root Nodule Cytosol via Xanthine Dehydrogenase.
PubMed:Fibrin membrane endowed with biological function. V. Multienzyme complex of uricase, catalase, allantoinase and allantoicase.
PubMed:Transport of nitrogen in the xylem of soybean plants.
PubMed:Allantoin and Allantoic Acid in Tissues and Stem Exudate from Field-grown Soybean Plants.
PubMed:Allantoin and Allantoic Acid in the Nitrogen Economy of the Cowpea (Vigna unguiculata [L.] Walp.).
PubMed:Effects of Allopurinol [4-Hydroxypyrazolo(3,4-d)Pyrimidine] on the Metabolism of Allantoin in Soybean Plants.
PubMed:The metabolism of caffeine by a Pseudomonas putida strain.
PubMed:[Microbial breakdown of caffeine (author's transl)].
PubMed:Stereospecificity of conversion of uric acid into allantoic acid by enzymes of Canadida utilis.
PubMed:Genetic and metabolic control of the purine catabolic enzymes of Neurospora crasse.
PubMed:Metabolism of xanthine and hypoxanthine in the tea plant (Thea sinensis L.).
PubMed:Clustering of the genes for allantoin degradation in Saccharomyces cerevisiae.
PubMed:The effect of thiourea on ureide metabolism in Neurospora crassa.
PubMed:The molecular and crystal structure of the potassium salt of allantoic acid.
PubMed:[Variations of the pH of the allantoic fluid inoculated with influenzal virus; culture of the virus in allantoic fluid slightly acid].
PubMed:[Not Available].
 
Notes:
Isol. from coffee beans and leaves -- formerly called allantoic acid and amniotic acid.; Allantoic acid is the END product of Allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation (Purine metabolism). Although it is commonly accepted that allantoicase is lost in mammals, it has been identified in mice and humans. (PMID 11852104); A crystalline, transparent, colorless substance found in the allantoic liquid of the fetal calf
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