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

• ChemBase ID: 41
• Molecular Formular: C6H13N3O3
• Molecular Mass: 175.18572
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid
• IUPAC Traditional name: L-citrulline
• Synonyms: (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; (S)-2-氨基-5-脲戊酸; L-2-氨基-5-脲戊酸; L-瓜氨酸

Database IDs

• CAS Number: 372-75-8
• EC Number: 206-759-6
• MDL Number: MFCD00064397
• Beilstein Number: 1725416; 6055157
• Merck Index: 142331
• PubChem SID: 160963504; 46506583; 24892975
• PubChem CID: 9750

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.2682476
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.9319353
• LogD (pH = 7.4): -3.9377463
• Log P: -3.9319577
• Molar Refractivity: 41.329 cm^3
• Polarizability: 16.298895 Å^3
• Polar Surface Area: 118.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.27
• LOG S: -0.9
• Solubility (Water): 2.18e+01 g/l

PROPERTIES

Physical Property

• Solubility: 200 g/L (at 20 oC); Water
• Apperance: White Solid
• Melting Point: 207-209°C (dec.); 212-214°C dec.; 220-221 °C
• Optical Rotation: [α]20/D +22.0±1°, c = 2% in 1 M HCl; +22 (c=2 in 1N HCl)
• Hydrophobicity(logP): -3.9

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥99.0% (NT); 98%
• Ignition Residue: ≤0.05%
• Cation Traces: 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
• Antion Traces: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Empirical Formula (Hill Notation): C6H13N3O3

DETAILS

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.

REFERENCES

• 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)