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Allantoic acid Sale

(Synonyms: 尿囊酸) 目录号 : GC60574

Allantoicacid是尿酸的降解产物,与嘌呤代谢有关。

Allantoic acid Chemical Structure

Cas No.:99-16-1

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产品描述

Allantoic acid is a degradative product of uric acid and associated with purine metabolism[1][2][3].

[1]. Taherkhani A, et, al. Metabolomic Analysis of Membranous Glomerulonephritis: Identification of a Diagnostic Panel and Pathogenic Pathways. Arch Med Res. 2019 May; 50(4):159-169. [2]. Okumura I, et, al. Stereospecificity of conversion of uric acid into allantoic acid by enzymes of Canadida utilis. J Biochem. 1976 May;79(5):1013-9. [3]. Cai HL, et, al. Therapeutic efficacy of atypical antipsychotic drugs by targeting multiple stress-related metabolic pathways. Transl Psychiatry. 2017 May 16; 7(5):e1130.

Chemical Properties

Cas No. 99-16-1 SDF
别名 尿囊酸
Canonical SMILES NC(NC(C(O)=O)NC(N)=O)=O
分子式 C4H8N4O4 分子量 176.13
溶解度 DMSO: 22.73 mg/mL (129.05 mM) 储存条件 Store at -20°C
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1 mM 5.6776 mL 28.3881 mL 56.7762 mL
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10 mM 0.5678 mL 2.8388 mL 5.6776 mL
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Research Update

Allantoic acid Synthesis in Soybean Root Nodule Cytosol via Xanthine Dehydrogenase

Plant Physiol 1980 Jun;65(6):1203-6.PMID:16661360DOI:10.1104/pp.65.6.1203.

Allantoin and Allantoic acid are the major forms of nitrogen transported from soybean nodules to other parts of the plant. Neither the pathway or the site of ureide synthesis has been demonstrated in root nodules.Bacteroid and cytosol (plant portion) fractions were prepared and the purity of each fraction was determined with marker enzymes. A pathway for ureide synthesis by the cytosol fraction of soybean nodules was established by measuring Allantoic acid or NADH production. Enzymes were found in the cytosol fraction which would synthesize Allantoic acid from the product of de novo purine synthesis, inosine-5'-monophosphate. Allantoic acid production by the nodule cytosol fraction with inosine-5'-monophosphate, inosine, xanthosine-5'-monophosphate, xanthosine, hypoxanthine, or xanthine as substrates was NAD(+)-dependent and blocked by allopurinol. Both bacteroid and cytosol fractions were capable of Allantoic acid production with uric acid or allantoin as substrates. Allantoic acid synthesis from these two substrates was neither dependent on NAD(+) nor inhibited by allopurinol.These data suggest that the xanthine-oxidizing enzyme in the nodule is an NAD(+)-dependent xanthine dehydrogenase (EC 1.2.1.37) which is present only in the cytosol fraction. The NADH production by this enzyme plays a critical and energy-conserving role in the ureide synthetic pathway. Cytosol xanthine dehydrogenase activity was sufficient for the metabolism of fixed N since calculations showed similar rates of N(2) fixation and xanthine oxidation.

Stereospecificity of conversion of uric acid into Allantoic acid by enzymes of Canadida utilis

J Biochem 1976 May;79(5):1013-9.PMID:986391DOI:10.1093/oxfordjournals.jbchem.a131141.

1. Allantoinase [EC 3.5.2.5] was isolated from cells of Candida utilis and unpurified by chromatography on columns of DEAE-cellulose and Sephadex G-200 after treatment with urea to remove urate oxidase [EC 1.7.3.3.]. 2. The purified allantoinase catalyzed the hydrolysis of allantoin into Allantoic acid. However, only half of the allantoin produced from uric acid by urate oxidase was converted. The rest of the allantoin was unchanged, and showed a negative optical rotation. 3. On the other hand, the combined action of crude urate oxidase and allantoinase resulted in nearly complete conversion of uric acid into Allantoic acid. Furthermore, the unpurified allantoinase preparation hydrolyzed racemic allantoin to Allantoic acid completely. 4. These results indicate that the urate oxidase produces racemic allantoin from uric acid and that the allantoinase attacks only allantoin of positive optical rotation. The results also suggest that allantoin racemase is present in the yeast cells.

Allantoin and Allantoic acid titre in the faeces and tissues of the developing larva of the moth, Orthaga exvinacea Hampson

Insect Biochem Mol Biol 1998 Dec;28(12):979-86.PMID:9887513DOI:10.1016/s0965-1748(98)00086-1.

Allantoin and Allantoic acid are investigated in the faeces and tissues of the developing sixth instar larva of the moth, Orthaga exvinacea. The nitrogen excreted as allantoin and Allantoic acid is compared with nitrogen excreted as uric acid and ammonia. The larva excretes 2.35-5.14 mumol/g allantoin and 0.74-1.34 mumol/g Allantoic acid which account for 0.83 to 2.39% and 0.23 to 0.53%, respectively, of the excreted total nitrogen. Allantoin and Allantoic acid are found to be minor nitrogenous end-products of the larva. Allantoin and Allantoic acid are also present in the haemolymph and fat body of the larva in varying concentrations. The level of allantoin in the haemolymph shows a negative correlation with the allantoin concentration of faeces and fat body. The allantoin is found to be stored in the fat body at a low level. The results of the present study also indicate the coexistence of uric acid storage and uricolysis.

Allantoin and Allantoic acid in the Nitrogen Economy of the Cowpea (Vigna unguiculata [L.] Walp.)

Plant Physiol 1978 Oct;62(4):495-8.PMID:16660546DOI:10.1104/pp.62.4.495.

The ureides, allantoin and Allantoic acid, represented major fractions of the soluble nitrogen pool of nodulated plants of cowpea (Vigna unguiculata [L.] Walp. cv. Caloona) throughout vegetative and reproductive growth. Stem and petioles were the principal sites of ureide accumulation, especially in early fruiting.Labeling studies using (14)CO(2) and (15)N(2) and incubation periods of 25 to 245 minutes indicated that synthesis of allantoin and Allantoic acid in root nodules involved currently delivered photosynthate and recently fixed N, and that the ureides were exported from nodule to shoot via the xylem. From 60 to 80% of xylem-borne N consisted of ureides; the remainder was glutamine, asparagine, and amino acids. Allantoin predominated in the soluble N fraction of nodules and fruits, allantoin and Allantoic acid were present in approximately equal proportions in xylem exudate, stems, and petioles.Extracts of the plant tissue fraction of nitrogen-fixing cowpea nodules contained glutamate synthase (EC 2.6.1.53) and glutamine synthetase (EC 6.3.1.2), but little activity of glutamate dehydrogenase (EC 1.4.1.3). High levels of uricase (EC 1.7.3.3) and allantoinase (EC 3.5.2.5) were also detected. Allantoinase but little uricase was found in extracts of leaflets, pods, and seeds.Balance sheets were constructed for production, storage, and utilization of ureide N during growth. Virtually all (average 92%) of the ureides exported from roots was metabolized on entering the shoot, the compounds being presumably used as N sources for protein synthesis.

Allantoin and Allantoic acid in Tissues and Stem Exudate from Field-grown Soybean Plants

Plant Physiol 1979 Mar;63(3):478-80.PMID:16660751DOI:10.1104/pp.63.3.478.

Samples of stem exudate and plant tissue collected from field-grown soybean (Glycine max [L.] Merr.) plants were analyzed for allantoin and Allantoic acid. Nitrogen in nitrate plus amino acids exceeded ureide N concentration in stem exudate prior to flowering. During all of reproductive development (from about 40 days after planting until maturity), ureide N concentration was two to six times greater than amino acid plus nitrate N concentration. Allantoin and Allantoic acid, not asparagine, are the principal forms of nitrogen transported from nodulated roots to shoots of the soybean plant. During pod and seed development ureide N comprised as high as 2.3, 37.7, and 15.8% of total N in leaf blades, stems + petioles, and fruits, respectively. The concentration of ureide in stems and fruits declined to nearly zero at maturity.Maximum ureide concentration of exudate collected from soybean nodules was 5.3 milligrams N per milliliter (94 micromoles allantoin per milliliter). This result supports evidence published by others that the site of allantoin synthesis is the nodule.