(2S)-2-amino-5-(carbamoylamino)pentanoic acid

• ChemBase编号: 41
• 分子式: C6H13N3O3
• 平均质量: 175.18572
• 单一同位素质量: 175.09569129
• SMILES: OC(=O)[C@@H](N)CCCNC(=O)N
• Canonical SMILES: NC(=O)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
• InChIKey: RHGKLRLOHDJJDR-BYPYZUCNSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-5-(carbamoylamino)pentanoic acid
• IUPAC传统名: L-citrulline
• 别名: (S)-2-氨基-5-脲戊酸; L-2-氨基-5-脲戊酸; L-瓜氨酸; (S)-2-Amino-5-ureidopentanoic acid; L-Citrulline; L-2-Amino-5-ureidovaleric acid; N5-(Aminocarbonyl)-L-ornithine; NSC 27425; Nδ-Carbamylornithine; α-Amino-δ-ureidovaleric Acid; δ-Ureidonorvaline; 2-Amino-5-uredovaleric acid; Sitrulline; Citrulline; delta-Ureidonorvaline; N5-carbamylornithine; N5-carbamoylornithine; N5-(Aminocarbonyl)ornithine; N5-Carbamoyl-L-ornithine; L-Citrulline; L-(+)-2-Amino-5-ureidovaleric acid

登记号

• CAS号: 372-75-8
• EC号: 206-759-6
• MDL号: MFCD00064397
• Beilstein号: 6055157; 1725416
• 默克索引号: 142331
• PubChem SID: 24892975; 160963504; 46506583
• PubChem CID: 9750

理论计算性质

JChem

• Acid pKa: 2.2682476
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -3.9319353
• LogD (pH = 7.4): -3.9377463
• Log P: -3.9319577
• 摩尔折射率: 41.329 cm^3
• 极化性: 16.298895 Å^3
• 极化表面积: 118.44 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.27
• LOG S: -0.9
• 溶解度: 2.18e+01 g/l

分子性质

理化性质

• 溶解度: 200 g/L (at 20 oC); Water
• 外观: White Solid
• 熔点: 207-209°C (dec.); 212-214°C dec.; 220-221 °C
• 比旋光度: [α]20/D +22.0±1°, c = 2% in 1 M HCl; +22 (c=2 in 1N HCl)
• 疏水性(logP): -3.9

安全信息

• 保存条件: 2-8°C; Refrigerator
• 德国WGK号: 3
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98% (TLC); ≥99.0% (NT); 98%
• 燃烧残渣: ≤0.05%
• 痕量阳离子: Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Empirical Formula (Hill Notation): C6H13N3O3

详细说明

MP Biomedicals - 05211125

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101397

Crystalline

DrugBank - DB00155

• Drug Groups: approved; nutraceutical
• Description: Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
• Indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - C7629

Biochem/physiol Actions
Intermediate in the production of nitric oxide from L-arginine by NO synthetase.
包装
10 mg in autosmp vl
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7629.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7629.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 27510

Other Notes
Substrate for the assay of argininosuccinate synthetase, EC 6.3.4.51

Toronto Research Chemicals - C535700

An amino acid, first isolated from the juice of watermelon, Citrullus vulgaris Schrad., Cucurbitaceae. Used in the treatment of asthenia.

参考文献

• Kurtz, et al.: J. Biol. Chem., 122, 477 (1938)
• Rajantie, J., et al.: J. Pediatr., 97, 927 (1938)
• Carpenter, T.O., et al.: N. Engl. J. Med., 312, 290 (1938)