(10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone; N-[(6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide

• ChemBase ID: 179531
• Molecular Formular: C71H84N10O17
• Molecular Mass: 1349.48346
• Monoisotopic Mass: 1348.60159128
• SMILES: c1cc(ccc1)CC1N(C(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@H]([C@H](OC(=O)[C@@H](NC(=O)[C@H]3N(C1=O)CCC(=O)C3)c1ccccc1)C)NC(=O)c1ncccc1O)CC)CCC2)C.O1C(=O)C2=CCCN2C(=O)c2nc(CC(=O)C[C@@H](/C=C(/C=C/CNC(=O)/C=C/[C@H]([C@H]1C(C)C)C)\C)O)oc2
• Canonical SMILES: O=C1NC/C=C/C(=C/[C@@H](O)CC(=O)Cc2nc(C(=O)N3C(=CCC3)C(=O)O[C@@H]([C@@H](/C=C/1)C)C(C)C)co2)/C.CC[C@@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)C(N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccccc1)CCC(=O)C2)c1ccccc1
• InChI: InChI=1S/C43H49N7O10.C28H35N3O7/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36;1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53);5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b;7-5+,10-9+,18-13+/t25-,29-,30+,31+,32?,34+,35+;19-,20-,26-/m11/s1
• InChIKey: MVTQIFVKRXBCHS-AGQHCAQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R,12E,17E,19E,21S)-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),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone; N-[(6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^6,^1^0]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• IUPAC Traditional name: (10R,11R,12E,17E,19E,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^3,^7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone; N-[(6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0^6,^1^0]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• Synonyms: Mikamycin; Streptogramin; Eskalin 500; Eskalin V; Lactrol; Livelong; Pyostacin; Pyostacine; Stafac; Stafac 20; Stafac 500; Stapyocine; Virgimycin; VirginiamycinDISCONTINUED

Database IDs

• CAS Number: 11006-76-1
• PubChem SID: 164235441
• PubChem CID: 71752965

CALCULATED PROPERTIES

• Acid pKa: 7.529842
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 1.8491545
• LogD (pH = 7.4): 1.6192802
• Log P: 1.8531505
• Molar Refractivity: 213.2372 cm^3
• Polarizability: 82.944954 Å^3
• Polar Surface Area: 224.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V673800

An antibiotic used in livestock feed to prevent disease among young swine. Also is used in ethanol production to prevent microbial contamination.

REFERENCES

• Cronly, M., et al.: J. Pharm. Biomed. Anal., 53, 929 (2010)
• Stewart, L., et al.: J. Animal Sci., 88, 1718 (2010)
• Xiao, J., et al.: Biosci., Biotechnol., Biochem., 74, 336 (2010)