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

• ChemBase ID: 105470
• Molecular Formular: C3H6N2O2
• Molecular Mass: 102.09194
• Monoisotopic Mass: 102.04292744
• SMILES: O=C1NOC[C@@H]1N
• 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-/m0/s1
• InChIKey: DYDCUQKUCUHJBH-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-amino-1,2-oxazolidin-3-one
• IUPAC Traditional name: (+)-cycloserine
• Synonyms: (S)-4-Amino-3-isoxazolidone; L-Cycloserine; L-4-Amino-3-Isoxazolidinone; L-CYCLOSERINE; (S)-4-AMinoisoxazolidin-3-one; 环丝氨酸

Database IDs

• CAS Number: 339-72-0
• EC Number: 206-427-0
• MDL Number: MFCD00064324
• Beilstein Number: 80799
• PubChem SID: 24278296; 162092510
• PubChem CID: 449215

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mg protein

Safety Information

• Storage Condition: 0°C, Desiccate
• RTECS: NY2976000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 97%

DETAILS

MP Biomedicals - 02190316

Crystalline
Antibiotic substance.
Inhibitor of transaminases.

Sigma Aldrich - C1159

包装
10, 25, 100 mg in poly bottle
250 mg in poly tube
Biochem/physiol Actions
Blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase. Cytotoxicity toward neuroblastoma and medulloblastoma cells mediated by suppression of ganglioside synthesis.1
L-cycloserine is a potent inhibitor of serine palmitoyltransferase, the first step of sphingolipid synthesis.