(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate

• ChemBase ID: 177546
• Molecular Formular: C37H45NO12
• Molecular Mass: 695.7527
• Monoisotopic Mass: 695.29417589
• SMILES: C1=C2C(=O)c3c(C1=O)c1c(c(c3O)C)O[C@@](C1=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)N2)/C)C)O)C)O)C)OC(=O)C)C)OC)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2C(=O)C=C(C(=O)c2c(c3C)O)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
• InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate
• Synonyms: 5,17,19,21-Tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone 21-Acetate; 1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin; Rifamycin S

Database IDs

• PubChem SID: 164233456
• PubChem CID: 12314965

CALCULATED PROPERTIES

• Acid pKa: 8.032118
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 3.3871052
• LogD (pH = 7.4): 3.2982008
• Log P: 3.3883674
• Molar Refractivity: 185.7171 cm^3
• Polarizability: 70.352135 Å^3
• Polar Surface Area: 194.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R508210

Semi-synthetic antibiotic.

REFERENCES

• Li, J., et al.: Bioorg. Med. Chem. Lett., 17, 5510 (2007)
• Patil, R., et al.: J. Pure & App. Microbiol., 2, 211 (2007)