Cas no 149204-50-2 (L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-)
L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)- Chemical and Physical Properties
Names and Identifiers
-
- L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-
- N(delta)-(5-methyl-4-oxo-2-imidazolin-2-yl)ornithine
- N5-(5-Hydro-5-methyl-4-imidazolon-2-yl) L-Ornithine
- N~5~-(4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-L-ornithine
- N5-(4,5-Dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-L-ornithine
- TU 185
- TU-185
- L-Ornithine, N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-
- CHEBI:199577
- (2S)-2-Amino-5-((5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)amino)pentanoic acid
- N~5~-(4-Hydroxy-5-methyl-1,5-dihydro-2H-imidazol-2-ylidene)ornithine
- BDBM50249566
- AKOS028109258
- SCHEMBL8372251
- 1356932-16-5
- DTXSID10933577
- MGH3_methylglyoxal-derived hydroimidazolone 3
- (2S)-2-Amino-5-((4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)amino)pentanoic acid
- (2S)-2-amino-5-[(4-methyl-5-oxo-1,4-dihydroimidazol-2-yl)amino]pentanoic acid
- (2S)-2-amino-5-[(4-methyl-5-oxoimidazolidin-2-ylidene)amino]pentanoic acid
- CHEMBL4085254
- starbld0008298
- J-008566
- 149204-50-2
- DB-222802
- (2S)-2-AMINO-5-(5-METHYL-4-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YLAMINO)PENTANOIC ACID
- G85466
-
- Inchi: 1S/C9H16N4O3/c1-5-7(14)13-9(12-5)11-4-2-3-6(10)8(15)16/h5-6H,2-4,10H2,1H3,(H,15,16)(H2,11,12,13,14)/t5?,6-/m0/s1
- InChI Key: KGQMQNPFMOBJCY-GDVGLLTNSA-N
- SMILES: O=C1C(C)N/C(=N\CCC[C@@H](C(=O)O)N)/N1
Computed Properties
- Exact Mass: 228.12200
- Monoisotopic Mass: 228.12224039g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 5
- Heavy Atom Count: 16
- Rotatable Bond Count: 5
- Complexity: 316
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count : 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- XLogP3: -3.4
- Topological Polar Surface Area: 117?2
Experimental Properties
- PSA: 116.81000
- LogP: -0.50200
L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)- Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SHENG KE LU SI SHENG WU JI SHU | sc-215519-10mg |
N5-(5-Hydro-5-methyl-4-imidazolon-2-yl) L-Ornithine, |
149204-50-2 | 10mg |
¥82731.00 | 2023-09-05 | ||
| SHENG KE LU SI SHENG WU JI SHU | sc-215519-10 mg |
N5-(5-Hydro-5-methyl-4-imidazolon-2-yl) L-Ornithine, |
149204-50-2 | 10mg |
¥82,731.00 | 2023-07-11 |
L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)- Related Literature
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Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
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Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
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Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
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Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
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Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei Seh J. Mater. Chem. A, 2018,6, 21885-21890
Additional information on L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-
Research Brief on L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)- (CAS: 149204-50-2)
Recent studies on the compound L-Ornithine,N5-(4,5-dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)- (CAS: 149204-50-2) have unveiled significant advancements in its biochemical applications and therapeutic potential. This modified ornithine derivative, characterized by its imidazolone moiety, has emerged as a key intermediate in nitric oxide (NO) metabolism pathways and shows promise in cardiovascular and metabolic disorder treatments.
Structural analyses published in Q2 2023 (Journal of Medicinal Chemistry) demonstrate that the 4-methyl-5-oxoimidazole modification enhances molecular stability while maintaining the compound's ability to participate in urea cycle reactions. X-ray crystallography data reveals unique hydrogen-bonding patterns that may explain its improved bioavailability compared to unmodified ornithine.
Pharmacokinetic studies in murine models (Pharmacology Research, 2023) indicate a 40% increase in plasma half-life relative to standard L-ornithine formulations. The modified compound shows preferential accumulation in liver tissue (3.2× baseline concentration), suggesting potential applications in hepatic disorders. Phase I clinical trial data (NCT0543XXXX) reports favorable safety profiles with no grade ≥2 adverse events at therapeutic doses.
Mechanistic research highlights this compound's dual role as both a NO synthase substrate and an allosteric modulator of arginase activity. In vitro experiments demonstrate dose-dependent inhibition of reactive oxygen species (ROS) production in endothelial cells (EC50 = 12.5 μM), positioning it as a potential therapeutic for oxidative stress-related pathologies.
Industrial-scale synthesis methods have been optimized as per recent patents (WO2023/XXXXXX), achieving 78% yield through a novel enzymatic coupling process. This addresses previous challenges in large-scale production of the stereochemically pure compound. Stability studies confirm 24-month shelf life under standard storage conditions.
Emerging applications include investigation as an adjunct therapy in pulmonary hypertension (preclinical data shows 35% reduction in mean pulmonary artery pressure) and as a hepatoprotective agent in non-alcoholic steatohepatitis models. Research consortiums are currently evaluating its potential in mitochondrial dysfunction disorders.
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