(2R,3S,4S,6R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.01,8]tetradecan-6-yl 2-hydroxyacetate

• ChemBase ID: 176827
• Molecular Formular: C22H34O5
• Molecular Mass: 378.50236
• Monoisotopic Mass: 378.24062419
• SMILES: [C@]1([C@H]([C@@H](C23[C@H](C([C@@H](C1)OC(=O)CO)([C@@H](CC3)C)C)C(=O)CC2)C)O)(C=C)C
• Canonical SMILES: OCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@@H](C23[C@H](C1(C)[C@H](C)CC2)C(=O)CC3)C
• InChI: InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21?,22?/m1/s1
• InChIKey: ZRZNJUXESFHSIO-JKZASVEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,6R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-hydroxyacetate
• IUPAC Traditional name: (2R,3S,4S,6R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-hydroxyacetate
• Synonyms: 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; Pleuromulin; Pleuromutilin

Database IDs

• CAS Number: 125-65-5
• PubChem SID: 164232737
• PubChem CID: 46782767

CALCULATED PROPERTIES

• Acid pKa: 13.105548
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.5980299
• LogD (pH = 7.4): 2.5980291
• Log P: 2.5980299
• Molar Refractivity: 102.2426 cm^3
• Polarizability: 40.9125 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 170-171°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P610500

Antibiotic substance produced by the basidiomycetes Pleurotus mutilus.

REFERENCES

• Anchel, et al.: J. Biol. Chem., 199,133 (1952)
• Knauseder, F., et al.: J. Antibiot., 29, 125 (1952)
• Brooks, G., et al.: Bioorg. Med. Chem., 9, 1221 (1952)
• Fritsche, T., et al.: Diagn. Microbiol. Infect. Dis., 52, 195 (1952)