| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Histidinol dehydrogenase (G. candidum); urocanase (competitive inhibitor). Imidazole-5-propionic acid is a potent inhibitor of G. candidum histidinol dehydrogenase (IC50 as low as 3.17 uM). Also competitive inhibitor of urocanase, which converts urocanate to imidazolone propionate in histidine metabolism.
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|---|---|
| ln Vitro |
Potent inhibitor of G. candidum histidinol dehydrogenase (IC50 as low as 3.17 uM). Urinary metabolite of L-histidine, involved in histidine catabolism via oxidation or transamination. Used in research of intestinal diseases and cardiovascular diseases, though specific mechanisms require elucidation.
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| ln Vivo |
Endogenous metabolite of histidine, present in urine, serves as biomarker of histidine metabolism. Involved in histidine degradation pathway via urocanate intermediate; competitive inhibitor of urocanase. Altered levels may be associated with intestinal diseases (e.g., IBD) and cardiovascular diseases where histidine metabolism is dysregulated.
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| Enzyme Assay |
(1) Histidinol dehydrogenase inhibition: incubate purified G. candidum histidinol dehydrogenase (0.1-1 ug) with L-histidinol (0.5-2 mM), NAD+ (1-2 mM) in 100 mM Tris-HCl pH9.0, and imidazole-5-propionic acid (0.1-100 uM). (2) Monitor NAD+ reduction to NADH at 340 nm over 5-30 min. (3) Calculate IC50. (4) Urocanase inhibition: incubate urocanase (0.1-1 ug) with urocanate (0.1-1 mM) in 50 mM Tris-HCl pH8.0 at 37degC, add compound (0.1-1000 uM), measure conversion to imidazolone propionate by UV at 275 nm.
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| Cell Assay |
(1) Seed intestinal epithelial cells (Caco-2, HT-29) or cardiomyocytes (5×10⁵/well). (2) Treat with imidazole-5-propionic acid (0.1-1000 uM) for 6-24 h. (3) For histidine metabolism: add 14C-L-histidine (1 uCi/mL) with/without compound (10-500 uM), incubate 4-8 h, separate histidine metabolites by HPLC, quantify radiolabeled imidazole-5-propionic acid. (4) For inflammation: pre-treat with compound (10-200 uM) 1-2 h, then stimulate with TNF-alpha/IL-1beta, measure cytokines by ELISA. (5) Cell viability: treat 0.1-10 mM for 48 h, MTT; non-toxic up to 2 mM.
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| Animal Protocol |
(1) For PK: use male C57BL/6 mice (20-25 g) or SD rats (200-250 g). (2) Administer imidazole-5-propionic acid by oral gavage (10-100 mg/kg) or IV (2-20 mg/kg) in sterile saline/PBS pH7.0-7.4. (3) Collect blood at 0,0.5,1,2,4,8,12,24 h, plasma deproteinized with 3 vol ice-cold acetonitrile containing IS. (4) Analyze by LC-MS/MS (ESI+, MRM 141→95). (5) Collect 24-h urine in metabolic cages. (6) For disease models: use DSS-induced colitis (2-3% DSS in water for 7 days) or high-fat diet-induced CVD, administer compound (10-50 mg/kg PO daily) for 2-4 weeks, assess disease severity (colon length, histology, cytokines; blood pressure, lipid profile, cardiac function).
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| ADME/Pharmacokinetics |
Soluble in water (≥10 mg/mL), methanol, DMSO (≥30 mg/mL). For cell culture, prepare 10-100 mM stock in water or DMSO, filter sterilize. For in vivo, dissolve in sterile saline or PBS at 5-20 mg/mL. Storage: powder at -20degC for 3 years; solution at -20degC for 6 months, -80degC for 1 year. Stable at neutral pH.
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| Toxicity/Toxicokinetics |
In vitro: CCK-8 on HEK293 cells with imidazole-5-propionic acid 0.1-10 mM, 48 h, IC50 >5 mM. In vivo: acute oral LD50 in mice >1000 mg/kg; IV LD50 >200 mg/kg. High doses (>200 mg/kg IV) cause mild sedation and respiratory depression. No significant hepatotoxicity, nephrotoxicity, or carcinogenicity reported. For research use only.
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| References | |
| Additional Infomation |
Dihydrouric acid is a monocarboxylic acid, a derivative of propionic acid, in which a hydrogen atom at the 3-position is replaced by an imidazole-4-yl group. It belongs to the imidazole class of compounds and is also a monocarboxylic acid. Functionally, it is related to propionic acid. It is the conjugate acid of dihydrouric acid.
It has been reported that 3-(1H-imidazole-4-yl)propionic acid has been found in Coprinopsis atramentaria, and relevant data are available for reference. Imidazole-5-propionic acid is an endogenous urinary metabolite of L-histidine, formed via the histidine catabolic pathway. Potent inhibitor of histidinol dehydrogenase (IC50 3.17 uM) in fungi and competitive inhibitor of urocanase. Studied in intestinal diseases (inflammatory bowel disease) and cardiovascular diseases where histidine metabolism is altered. Potential biomarker or therapeutic target. Not FDA-approved; strictly for research use. |
| Molecular Formula |
C6H8N2O2
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|---|---|
| Molecular Weight |
140.14
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| Exact Mass |
140.059
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| CAS # |
1074-59-5
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| PubChem CID |
70630
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.335g/cm3
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| Boiling Point |
427.4ºC at 760 mmHg
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| Melting Point |
206 - 208 °C
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| Flash Point |
212.3ºC
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| Vapour Pressure |
4.57E-08mmHg at 25°C
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| Index of Refraction |
1.571
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| LogP |
0.426
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
10
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| Complexity |
127
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(NC=N1)CCC(=O)O
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| InChi Key |
ZCKYOWGFRHAZIQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
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| Chemical Name |
3-(1H-imidazol-5-yl)propanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O :~100 mg/mL (~713.57 mM)
DMSO :< 1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.1357 mL | 35.6786 mL | 71.3572 mL | |
| 5 mM | 1.4271 mL | 7.1357 mL | 14.2714 mL | |
| 10 mM | 0.7136 mL | 3.5679 mL | 7.1357 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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