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22862-76-6 molecular structure
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(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 and InChIs

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

Cite this record

CBID:5025 http://www.chembase.cn/molecule-5025.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
22862-76-6
EC Number
245-269-7
MDL Number
MFCD00077650
Beilstein Number
20705
PubChem SID
24891496
160968457
99443845
PubChem CID
253602

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.766854  H Acceptors
H Donor LogD (pH = 5.5) -2.3863556 
LogD (pH = 7.4) -1.0800986  Log P 0.73128223 
Molar Refractivity 69.3019 cm3 Polarizability 27.932943 Å3
Polar Surface Area 67.79 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.97  LOG S -2.11 
Solubility (Water) 2.07e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble20 mg/mL expand Show data source
H2O: soluble2 mg/mL (Aqueous solutions are stable over a wide range of pH at room temperature.) expand Show data source
methanol: soluble20 mg/mL expand Show data source
methanol: soluble20 mg/mL, clear, colorless to faintly yellow expand Show data source
Apperance
white to faint yellow solid expand Show data source
RTECS
BZ9800000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
3462 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
Safety Statements
45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3462 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥96.0% (TLC) expand Show data source
≥98% (HPLC) expand Show data source
Quality Level
PREMIUM expand Show data source
Empirical Formula (Hill Notation)
C14H19NO4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB07374 external link
Drug information: experimental
Sigma Aldrich - A9789 external link
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 external link
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.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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