(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate

• ChemBase ID: 5025
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: c1c(ccc(c1)C[C@@H]1[C@@H]([C@H](CN1)O)OC(=O)C)OC
• Canonical SMILES: COc1ccc(cc1)C[C@H]1NC[C@@H]([C@H]1OC(=O)C)O
• InChI: InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
• InChIKey: YKJYKKNCCRKFSL-RDBSUJKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
• IUPAC Traditional name: anisomycin
• Synonyms: ANISOMYCIN; (2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate; 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate; Flagecidin; Anisomycin from Streptomyces griseolus

Database IDs

• CAS Number: 22862-76-6
• EC Number: 245-269-7
• MDL Number: MFCD00077650
• Beilstein Number: 20705
• PubChem SID: 160968457; 99443845; 24891496
• PubChem CID: 253602

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.766854
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.3863556
• LogD (pH = 7.4): -1.0800986
• Log P: 0.73128223
• Molar Refractivity: 69.3019 cm^3
• Polarizability: 27.932943 Å^3
• Polar Surface Area: 67.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.97
• LOG S: -2.11
• Solubility (Water): 2.07e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL; H2O: soluble2 mg/mL (Aqueous solutions are stable over a wide range of pH at room temperature.); methanol: soluble20 mg/mL; methanol: soluble20 mg/mL, clear, colorless to faintly yellow
• Apperance: white to faint yellow solid

Safety Information

• RTECS: BZ9800000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (TLC); ≥98% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C14H19NO4

DETAILS

DrugBank - DB07374

Drug information: experimental

Sigma Aldrich - A9789

Caution
Hygroscopic
Biochem/physiol Actions
Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.

Sigma Aldrich - 10522

Other Notes
Inhibits formation of the 80S ribosomal complex from 60S subunits.1
Biochem/physiol Actions
Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.