(6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone

• ChemBase ID: 165291
• Molecular Formular: C34H50N4O9S
• Molecular Mass: 690.8472
• Monoisotopic Mass: 690.3298502
• SMILES: O1C(=O)[C@@H]2N(C(=O)c3nc(CC(=O)C[C@@H](/C=C(/C=C/CNC(=O)/C=C/[C@H]([C@H]1C(C)C)C)\C)O)oc3)CC[C@H]2S(=O)(=O)CCN(CC)CC
• Canonical SMILES: CCN(CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc1nc(C2=O)co1)O)/C)CC
• InChI: InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1
• InChIKey: SUYRLXYYZQTJHF-VMBLUXKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
• IUPAC Traditional name: (6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethanesulfonyl]-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
• Synonyms: (3R,4R,5E,10E,12E,14S,26R,26aS)-26-[[2-(Diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a-octahydro-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone; (26R,27S)-26-[[2-(diethylamino)ethyl]sulfonyl]-26,27-dihydrovirginiamycin M1; RP 54476; DalfopristinDISCONTINUED

Database IDs

• CAS Number: 112362-50-2
• PubChem SID: 162259424
• PubChem CID: 6323289

CALCULATED PROPERTIES

• Acid pKa: 11.378627
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -0.012025763
• LogD (pH = 7.4): 1.4094774
• Log P: 1.581891
• Molar Refractivity: 182.8398 cm^3
• Polarizability: 70.6918 Å^3
• Polar Surface Area: 176.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D120000

A Viiginiamycin M1 (V672810) derivative. A streptogramin antibiotic used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

REFERENCES

• Le Bouter, A. et al.: Int. J. Antimicrob. Ag., 37, 118 (2011)
• Allington, D.R. et al.: Clin. Ther., 23, 23 (2011)
• Keshari, S.S. et al.: Ind. J. Pharmacol., 41, 47 (2011)
• Mitrano, J.A. et al.: Pharmacotherapy, 29, 1103 (2011)