(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-({1-[(2R)-2-amino-3-methylbutanamido]-2-(2H3)methyl(3,3,3-2H3)propan-2-yl}sulfanyl)acetate

• ChemBase ID: 179434
• Molecular Formular: C31H52N2O5S
• Molecular Mass: 564.81998
• Monoisotopic Mass: 564.35969377
• SMILES: [C@H]12[C@@]3(CCC1=O)[C@H]([C@@H]([C@@](C[C@H]([C@@]2([C@H](CC3)C)C)OC(=O)CSC(CNC(=O)[C@@H](C(C)C)N)(C)C)(C=C)C)O)C
• Canonical SMILES: C=C[C@]1(C)C[C@@H](OC(=O)CSC(CNC(=O)[C@@H](C(C)C)N)(C)C)[C@]2(C)[C@@H](C)CC[C@]3([C@H]([C@@H]1O)C)[C@H]2C(=O)CC3
• InChI: InChI=1S/C31H52N2O5S/c1-10-29(8)15-22(38-23(35)16-39-28(6,7)17-33-27(37)24(32)18(2)3)30(9)19(4)11-13-31(20(5)26(29)36)14-12-21(34)25(30)31/h10,18-20,22,24-26,36H,1,11-17,32H2,2-9H3,(H,33,37)/t19-,20+,22-,24-,25+,26+,29-,30+,31+/m1/s1
• InChIKey: LLYYNOVSVPBRGV-MVNKZKPCSA-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-({1-[(2R)-2-amino-3-methylbutanamido]-2-(^2H₃)methyl(3,3,3-^2H₃)propan-2-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-({1-[(2R)-2-amino-3-methylbutanamido]-2-(^2H₃)methyl(3,3,3-^2H₃)propan-2-yl}sulfanyl)acetate
• Synonyms: 2-[[2-[[(2R)-2-Amino-3-methyl-1-oxobutyl]amino]-1,1-dimethylethyl-d6]thio]acetic 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; Econor-d6; Valnemulin-d6

Database IDs

• PubChem SID: 164235344
• PubChem CID: 71752906

CALCULATED PROPERTIES

• Acid pKa: 14.363035
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2456743
• LogD (pH = 7.4): 2.8274221
• Log P: 3.9686627
• Molar Refractivity: 156.468 cm^3
• Polarizability: 62.65787 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V094402

Labelled semisynthetic antibiotic; derivative of pleuromutilin. Antibacterial.

REFERENCES

• Horkovics-Kovats, S., et al.: J. Pharm. Med., 6, 149 (1996)
• Jordan, F.T.W., et al.: Avian Dis., 42, 738 (1996)
• Aitken, I.A., et al.: Vet. Rec., 144, 128 (1996)
• Poulsen, S.M., et al.: Mol. Microbiol., 41, 1091 (1996)