(4R)-4-amino-1,2-oxazolidin-3-one

• ChemBase ID: 2824
• Molecular Formular: C3H6N2O2
• Molecular Mass: 102.09194
• Monoisotopic Mass: 102.04292744
• SMILES: N[C@@H]1CONC1=O
• Canonical SMILES: N[C@@H]1CONC1=O
• InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
• InChIKey: DYDCUQKUCUHJBH-UWTATZPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-amino-1,2-oxazolidin-3-one
• IUPAC Traditional name: (R)-4-amino-isoxazolidin-3-one; cycloserine; (4R)-4-amino-1,2-oxazolidin-3-one
• Brand Name: Seromycin
• Synonyms: (R)-4-Amino-Isoxazolidin-3-One; Seromycin; D-Cycloserine; (R)-4-Amino-3-isoxazolidone; 4-Amino-3-isoxazolidinone; (4R)-4-Amino-3-isoxazolidinone; (+)-4-Amino-3-isoxazolidinone; (+)-Cycloserine; (R)-(+)-Cycloserine; (R)-4-Amino-3-isoxazolidinone; (R)-Cycloserine; Closerin; Closina; Cyclo-D-serine; Cyclorin; Cycloserine; D-4-Amino-3-isoxazolidone; D-CS; Farmiserina; Micoserina; Miroseryn; NSC 154851; NSC 76029; Novoserin; Orientomycin; Oxamycin; PA 94; Tisomycin; Wasserina; α-Cycloserine; D-Cycloserine; Cycloserine; (R)-4-aminoisoxazolidin-3-one; D-4-amino-3-isoxazolidinone; R (+)-4-amino-3-isoxazolidinone; D-CYCLOSERINE γ-IRRADIATED; Cyclomycin; Oxymycin; Antibiotic 106-7; Antibiotic 5915; Antibiotic 8217; Antibiotic 17452; Antibiotic E 733A; Antibiotic I 1431; Antibiotic K 300; Antibiotic NJ 21; Antibiotic PA 94; Antibiotic Ro 1-9213; Orientmycin; Cycloserine; (4R)-4-amino-1,2-oxazolidin-3-one; d-4-amino-3-isoxazolidinone; (R)-4-氨基-3-异噁唑烷酮; 4-氨基-3-异噁唑烷酮; D-环丝氨酸

Database IDs

• CAS Number: 68-41-7
• EC Number: 200-688-4
• MDL Number: MFCD00005353
• Beilstein Number: 80798
• PubChem SID: 24892907; 24277962; 160966272; 24892979; 24858076
• PubChem CID: 6234
• CHEBI ID: 40009
• ATC CODE: J04AB01
• CHEMBL: 771
• Chemspider ID: 5998
• DrugBank ID: DB00260
• KEGG ID: D00877
• Unique Ingredient Identifier: 95IK5KI84Z
• Wikipedia Title: Cycloserine

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.210087
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.4357781
• LogD (pH = 7.4): -2.4206417
• Log P: -2.4213324
• Molar Refractivity: 21.8488 cm^3
• Polarizability: 9.062646 Å^3
• Polar Surface Area: 64.35 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.31
• LOG S: 0.93
• Solubility (Water): 8.77e+02 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M phosphate pH 8.0: soluble10 mg/mL (as a stock solution)
• Apperance: powder
• Melting Point: 147 - 149°C; 147 °C (dec.)(lit.); 147°C (decomposes)
• Optical Rotation: [α]20/D +115.0±5.0°, c = 2% in H2O
• Hydrophobicity(logP): -1.192

Safety Information

• Storage Condition: 0°C; -20°C; 2-8°C, Desiccate
• Storage Warning: IRRITANT
• RTECS: NY2975000
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Bioavailability: ~70% to 90%
• Excretion: Renal
• Half Life: 10 hrs (normal renal function)
• Metabolism: Hepatic
• Pregnancy Category: C
• Gene Information: human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907)mouse ... GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168)rat ... GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668); human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)
• Mechanism of Action: Antagonizes the role of D-alanine in bacterial cell-wall-synthesis; Inhibits cell-wall-synthesis in: Mycobacterium tuberculosis; Susceptible strains of gram-negative bacteria; Susceptible strains of gram-positive bacteria

Product Information

• Purity: ≥96.0% (NT); 95%; 95+%; 98%
• Salt Data: Free Base
• Biological Source: Prod. by Streptomyces garyphalus, Streptomyces orchidaceus, Streptomyces lavendulae and Streptomyces nagasakiensis; synthetic
• Sterility: γ-irradiated
• Application(s): Shows antibiotic activity primarily against mycobacteria; Tuberculostatic
• Empirical Formula (Hill Notation): C3H6N2O2

DETAILS

MP Biomedicals - 02100535

Crystalline
Synthetic
Bactericidal antibiotic.

MP Biomedicals - 02194788

Synthetic
γ-Irradiated
Molecular Biology Reagent
Inhibits cell wall synthesis.

DrugBank - DB03123

Drug information: experimental

Selleck Chemicals - S1998

Research Area: Infection
Biological Activity:
D-Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis. [1]

Sigma Aldrich - C7670

Application
分子生物应用建议浓度 100-200μg/mL。
Biochem/physiol Actions
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
作用方式：抑制细胞壁的生物合成（D-Ala 肽键的形成）。也会阻碍 D-Ala 向 L-Ala 的转化。抑菌。 抗性机理：干扰 D-Ala 转运。
Reconstitution
直接用小瓶配制推荐范围内任意浓度的储备液。在溶液中不稳定；配制后立即使用。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C6880

Biochem/physiol Actions
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
作用方式：抑制细胞壁的生物合成（D-Ala 肽键的形成）。也会阻碍 D-Ala 向 L-Ala 的转化。抑菌。 抗性机理：干扰 D-Ala 转运。
包装
1, 5 g in poly bottle

Sigma Aldrich - 30020

Application
Cycloserine is used to inhibit various enzymes.
Biochem/physiol Actions
Mode of Action: Inhibits cell wall biosynthesis (D-Ala peptide bond formation). Also prevents conversion of D-Ala to L-Ala. Bacteriostatic.Mode of Resistance: D-Ala transport interference.
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
Mode of Action: Inhibits cell wall biosynthesis (D-Ala peptide bond formation). Also prevents conversion of D-Ala to L-Ala. Bacteriostatic. Mode of Resistance: D-Ala transport interference.
Other Notes
D-Cycloserine acts as inhibitor of various enzymes.1
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C3909

Biochem/physiol Actions
Partial agonist at the glycine modulatory site of NMDA glutamatergic receptors; antibiotic against Gram-negative bacteria.
作用方式：抑制细胞壁的生物合成（D-Ala 肽键的形成）。也会阻碍 D-Ala 向 L-Ala 的转化。抑菌。 抗性机理：干扰 D-Ala 转运。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Toronto Research Chemicals - C988815

D-Cycloserine inhibits cell wall biosynthesis (D-Ala peptide bond formation). D-Cycloserine also prevents conversion of D-Ala to L-Ala. D-Cycloserine is an bacteriostatic. D-Cycloserine is an antibiotic against Gram-negative bacteria.

REFERENCES

• http://www.drugbank.ca/drugs/DB00260
• Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972)
• Gentry-Weeks, C., et al.: J. Biol. Chem., 268, 7298 (1972)
• Alexander, F., et al.: Eur. J. Biochem., 219, 953 (1972)
• Auger, S., et al.: Biochimie, 87, 231 (1972)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 810A; 810D; 811A, (ir)
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 1, 678B; 678C; 678D, (nmr)
• Harned, R.L. et al., Antibiot. Chemother. (Washington, D.C.), 1955, 5, 204, (struct)
• Stammer, C.H. et al., J.A.C.S., 1955, 77, 2344; 2345; 2346; 1957, 79, 3236, (struct, synth, isol, resoln)
• Neuhaus, F.C., Antibiotics (N.Y.), 1967, 1, 40, (rev)
• Milne, G.W.A. et al., Tetrahedron, 1967, 23, 65, (nmr, ms)
• Lamb, J.W., Anal. Profiles Drug Subst., 1972, 1, 53, (rev, synth, anal)
• O'Brien, P., Met. Ions Biol. Syst., 1985, 19, 295, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 107, (synonyms)
• El-Obeid, H.A. et al., Anal. Profiles Drug Subst., 1989, 18, 567, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 156
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CQH000