(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.01,8]tetradecan-6-yl 2-{[(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate

• ChemBase ID: 179899
• Molecular Formular: C30H47NO4S
• Molecular Mass: 517.76348
• Monoisotopic Mass: 517.32257999
• SMILES: [C@@]123[C@H]([C@]([C@@H](C[C@]([C@H]([C@@H]1C)O)(C=C)C)OC(=O)CS[C@@H]1C[C@@H]4N([C@H](C1)CC4)C)([C@@H](CC3)C)C)C(=O)CC2
• Canonical SMILES: C=C[C@]1(C)C[C@@H](OC(=O)CS[C@@H]2C[C@H]3CC[C@@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3([C@H]([C@@H]1O)C)[C@H]2C(=O)CC3
• InChI: InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20?,21?,22?,24-,26+,27+,28-,29+,30+/m1/s1
• InChIKey: STZYTFJPGGDRJD-OSBNDYPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-{[(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate
• IUPAC Traditional name: (1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^1,^8]tetradecan-6-yl 2-{[(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate; altabax (glaxo)
• Synonyms: Altabax; Altargo; Retapamulin; Retapamulin

Database IDs

• CAS Number: 224452-66-8
• PubChem SID: 164235809
• PubChem CID: 6918462

CALCULATED PROPERTIES

• Acid pKa: 14.425539
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.9535479
• LogD (pH = 7.4): 2.1104655
• Log P: 4.3734345
• Molar Refractivity: 145.4515 cm^3
• Polarizability: 58.145725 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Target: Others
• Mechanism of Action: Inhibit protein synthesis in bacteria by binding to the peptidyl transferase component of the 50S subunit of ribosomes

Product Information

• Salt Data: Free Base
• Application(s): Pleuromutilin antibiotic

REFERENCES

• 1. Jones R, Fritsche T, Sader H, Ross J (2006). "Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci". Antimicrob Agents Chemother 50 (7): 2583?
• .
• 2. Physicans' Desk Reference(ISBN 1-56363-660-3) (62 ed.). 2007. pp. 1318?0.