(2S)-2-amino-3-carbamoylpropanoic acid

• ChemBase ID: 59
• Molecular Formular: C4H8N2O3
• Molecular Mass: 132.11792
• Monoisotopic Mass: 132.05349213
• SMILES: OC(=O)[C@@H](N)CC(=O)N
• Canonical SMILES: NC(=O)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
• InChIKey: DCXYFEDJOCDNAF-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-carbamoylpropanoic acid
• IUPAC Traditional name: L-asparagine
• Brand Name: Agedoite; Altheine; Crystal VI
• Synonyms: (S)-2-Aminosuccinic acid 4-amide; L-Aspartic acid 4-amide; L-(+)-Asparagine; (-)-Asparagine; (S)-Asparagine; (S)-2,4-Diamino-4-oxobutanoic acid; a-Aminosuccinamic acid; 2-Aminosuccinamic acid; Asn; Asparagine; Asparagine acid; Aspartic acid b-amide; Aspartic acid amide; Aspartamic acid; Asparamide; L-Aspartamine; L-2,4-Diamino-4-oxobutanoic acid; L-b-Asparagine; L-Asparagine; L-Asparagine anhydrous; L-Asparagine; 2-Amino-3-carbamoylpropanoic acid; Asparagine; (S)-2-Aminosuccinic acid 4-amide, L-Aspartic acid 4-amide; L-(+)-无水天冬酰胺酸; (S)-2-氨基琥珀酸-4-酰胺; L-天冬氨酸-4-酰胺; L-天冬酰胺

Database IDs

• CAS Number: 70-47-3
• EC Number: 200-735-9
• MDL Number: MFCD00064401
• Beilstein Number: 1723527
• Merck Index: 14837
• PubChem SID: 46507804; 24890831; 24847033; 24890464; 160963522
• PubChem CID: 6267; 236
• CHEBI ID: 17196
• CHEMBL: 58832
• Chemspider ID: 6031
• DrugBank ID: DB03943
• KEGG ID: C00152
• Unique Ingredient Identifier: 7NG0A2TUHQ
• Wikipedia Title: Asparagine

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9985391
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.2879124
• LogD (pH = 7.4): -4.3236184
• Log P: -4.287831
• Molar Refractivity: 28.3549 cm^3
• Polarizability: 11.510928 Å^3
• Polar Surface Area: 106.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.36
• LOG S: 0.1
• Solubility (Water): 1.68e+02 g/l

PROPERTIES

Physical Property

• Solubility: 29.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; H2O: soluble0.1 M at 20 °C, clear, colorless
• Melting Point: 234-236°C; 234-236°C dec.; 235 °C (dec.)(lit.); 235°C
• Optical Rotation: [α]20/D +28.3°, c = 13.2 in 1 M HCl; [α]20/D +35.0±0.5°, c = 5% in 5 M HCl
• Absorption Wavelength: λ: 260 nm Amax: 0.07; λ: 280 nm Amax: 0.06
• Hydrophobicity(logP): -4.4
• pKa: 2.02 (carboxyl), 8.8 (amino)
• pH: 4.0-5.5 (25 °C, 0.1 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Hygroscopic; IRRITANT
• German water hazard class: 1
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥99.0% (NT); ≥99.5% (NT); 99%
• Grade: certified reference material; TraceCERT®
• Suitability: suitable for cell culture; suitable for insect cell culture
• Ignition Residue: ≤0.05% (as SO4); ≤0.1% (as SO4)
• Impurities: ≤0.1% foreign amino acids; ≤1% foreign amino acids; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤200 mg/kg; Ca: ≤50 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: ≤50 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Quality Level: ELITE
• λ: 0.1 M in H2O
• Product Line: BioUltra
• Linear Formula: H2NCOCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02100794

Crystalline
Purity: 99%

MP Biomedicals - 02194630

Cell Culture Reagent
Anhydrous
Crystalline
Purity: 99%

DrugBank - DB00174

• Drug Groups: approved; nutraceutical
• Description: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from aspartic acid and ammonia by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed)
• Indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: A non-essential amino acid. Asparagine is critical for the production of the body's proteins, enzymes and muscle tissue. Supplements of this amino acid are claimed to balance nervous system function.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - A0884

包装
1 kg in poly bottle
10 mg in autosmp vl
25, 100, 500 g in poly bottle

Sigma Aldrich - 11149

Other Notes
As spacer in isotachophoresis1,2; Growth requirement of various microorganisms3.

Sigma Aldrich - 51363

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC