Basic information
- CAS
22862-76-6- Standard SMILES
COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1- InChIKey
YKJYKKNCCRKFSL-RDBSUJKOSA-N- Molecular formula
- C14H19NO4
- Average molar mass
- 265.3 g/mol
- Monoisotopic mass
- 265.13140809
Overview
(-)-anisomycin is an antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. It has a role as an anticoronaviral agent, an antimicrobial agent, an antiparasitic agent, an antineoplastic agent, a protein synthesis inhibitor, a DNA synthesis inhibitor and a bacterial metabolite. It is an organonitrogen heterocyclic antibiotic and a monohydroxypyrrolidine.
Names & identifiers
- Preferred name
- Anisomycin
- IUPAC
- [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
- English name
- ANISOMYCIN
- Molecular formula
- C14H19NO4
- Molecular weight
- 265.3
Names & synonyms
anisomycin22862-76-6Flagecidin(-)-Anisomycin(2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetateNSC-76712(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetateNSC767126C74YM2NGI[(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetateDTXSID5040966
Show more names
Nsc147340Aids031977Aids-031977Wuningmeisu C4-beta))-alphAnisomycin>(-)-anisomycin
CHEBI:338412(2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine(2R,3S,4S)-2-((4-Methoxyphenyl)methyl)-3,4-pyrrolidinediol 3-acetate(2R,3S,4S)-2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R,3S,4S)-3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate, (2R,3S,4S)-3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R-(2alpha,3alpha,4beta))-((2R,3S,4S)-4-hydroxy-2-((4-methoxyphenyl)methyl)pyrrolidin-3-yl) acetate
Database identifiers
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 67.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 302
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section165.8 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 140 · 140-141 C
- alpha
- 23 · D23 -30° (methanol)
- Boiling point
- 408.52 °C · 408.52°C (rough estimate)
- Density
- 1.1356 · 1.1356 (rough estimate)
- refractive index
- 1.523 · 1.5230 (estimate)
- Flash point
- 87 ℃ · 87℃
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 20 mg/mL, · methanol: 20 mg/mL, clear, colorless to faintly yellow
- form
- solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (98.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 65 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStreptomyces griseolus: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - D-xylo-Pentitol, 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-, 3-acetate: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (98.5%)
Safety data
- F
- 3-10
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- BZ9800000
- ridadr
- UN 3462 6.1/PG 3
- hs_code
- 29419090
- Toxicity
- LD50 orl-rat: 72 mg/kg ANTCAO 5,490,55
- risk_code
- 25-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that are destructive to protozoans.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Compounds that inhibit cell production of DNA or RNA.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionAnisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable.
UsesAnisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells.
UsesIt is applied as an antiparasitic agent and antineoplastic agent. It acts as a protein synthesis inhibitor (blocks translation), potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. It also scts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK).
Suppliers102 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Related reactions
5 records
Compound notes
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