ChemicalBook CAS DataBase List 125-65-5

125-65-5

Name	Pleuromulin
CAS	125-65-5
EINECS(EC#)	204-747-5
Molecular Formula	C22H34O5
MDL Number	MFCD00864911
Molecular Weight	378.5
MOL File	125-65-5.mol

Synonyms

bc757 a4014c NSC 121145 PLEUROMULIN drosopholinb PLEUROMUTILIN Drosophilin B antibioticbc757 PleuroMulin 95% 97% Mutilin 14-glycolate Drosophilin B, A 40104C PleuroMutilin antibacterial drugs l-3a,9-propano-3ah-cyclopentacycloocten-1(4h)-one glycolicacid,8-esterwithoctahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-viny 5-Hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate Glycolic acid (10R)-6-ethenyldecahydro-5α-hydroxy-4β,6β,9β,10-tetramethyl-1-oxo-3aα,9α-propano-3aH-cyclopentacycloocten-8β-yl Glycolic acid, 8-ester with octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopentacycloocten-1(4H)-one Glycolic acid (10R)-6-ethenyldecahydro-5α-hydroxy-4β,6β,9β,10-tetramethyl-1-oxo-3aα,9α-propano-3aH-cyclopentacycloocten-8β-yl ester 2-Hydroxyacetic Acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl Ester Acetic acid, 2-hydroxy-, (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

Chemical Properties

Appearance	Crystalline Solid
Melting point	170-1710C
alpha	D24 +20° (c = 3 in abs ethanol)
Boiling point	482.8±45.0 °C(Predicted)
density	1.15±0.1 g/cm3(Predicted)
storage temp.	-20°C Freezer
solubility	DMSO: >10mg/mL (warmed)
form	powder
pka	12.91±0.10(Predicted)
color	white to beige
Optical Rotation	[α]/D +30 to +40° (c=1; CH2Cl2)
InChIKey	YSBXUHAJXRCCET-BKUNHTPHSA-N
SMILES	C(O[C@@H]1C[C@](C=C)(C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@]2([H])C(=O)CC3)(=O)CO

Safety Data

Symbol(GHS)	GHS07,GHS09
Signal word	Warning
Hazard statements	H302-H410
Precautionary statements	P264-P270-P273-P301+P312-P391-P501
WGK Germany	3
RTECS	MC5408000
REACH Registrations	Active
Toxicity	LD50 in mice: >60 mg/kg (Kavanagh, 1952) less more

Hazard Information

Chemical Properties

Crystalline Solid

Uses

Antibiotic substance produced by the basidiomycetes Pleurotus mutilus

Uses

Pleuromutilin is a diterpene produced by several species of basidomycete, notably the genus Pleurotus, discovered in 1951. Pleuromutilin is a potent and highly selective antibiotic active against a range of Gram positive bacteria, with no cross resistance to existing antibiotic classes due to its unique mode of action. Pleuromutilin inhibits protein synthesis by binding to domain V of 23S rRNA and this has led to the development of many semi-synthetic analogues as new generation antibiotics, such as tiamulin and retapamulin.

Uses

Pleuromutilin is a diterpene produced by several species of basidomycetes, notably the genus Pleurotus, discovered in 1951. Pleuromutilin is a potent and highly selective antibiotic active against a range of Gram positive bacteria, with no cross resistance to existing antibiotic classes due to its unique mode of action. Pleuromutilin inhibits protein synthesis by binding to domain V of 23S rRNA and this has led to the development of many semi-synthetic analogues as new generation antibiotics, such as tiamulin and retapamulin.

Description

Pleuromutilin is an antibiotic derived from the fungus Clitopilus that inhibits bacterial protein synthesis by binding to bacterial ribosomes in the peptidyl transferase component of the 50S subunit and inhibiting peptide bond formation.

References

[1]. kilaru s, collins cm, hartley aj, et al. establishing molecular tools for genetic manipulation of the pleuromutilin-producing fungus clitopilus passeckerianus. appl environ microbiol. 2009 nov;75(22):7196-204.
[2]. long ks, hansen lh, jakobsen l, et al. interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center. antimicrob agents chemother. 2006 apr;50(4):1458-62.

Material Safety Data Sheet(MSDS)

Spectrum Detail

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