(Z)-1-[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-26-yl]-N-(4-methylpiperazin-1-yl)methenimine oxide

• ChemBase ID: 177541
• Molecular Formular: C43H58N4O13
• Molecular Mass: 838.93962
• Monoisotopic Mass: 838.40003794
• SMILES: c1(c2c(c3c(c1O)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)O)/C=[N+](/N1CCN(CC1)C)\[O-]
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=[N+](/N4CCN(CC4)C)\[O-])c(c(c2c(c3C)O)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/C43H58N4O13/c1-21-12-11-13-22(2)42(55)44-33-28(20-47(56)46-17-15-45(9)16-18-46)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,60-40)58-19-14-29(57-10)23(3)39(59-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,44,55)/b12-11+,19-14+,22-13-,47-20-/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
• InChIKey: PADXLTATLMUKBQ-RIPAWWNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (Z)-1-[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-26-yl]-N-(4-methylpiperazin-1-yl)methenimine oxide
• IUPAC Traditional name: (Z)-1-[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-13-(acetyloxy)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-26-yl]-N-(4-methylpiperazin-1-yl)methenimine oxide
• Synonyms: 3-[[(4-Methyl-4-oxido-1-piperazinyl)imino]methyl]rifamycin; 3-[[(4-methyl-1-piperazinyl)imino]methyl]rifamycin N-4’-Oxide; Rifampicin N-4'-Oxide

Database IDs

• CAS Number: 51963-55-4
• PubChem SID: 164233451
• PubChem CID: 6441063

CALCULATED PROPERTIES

• Acid pKa: 6.9180784
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 1.1254236
• LogD (pH = 7.4): 2.160758
• Log P: 2.146728
• Molar Refractivity: 237.4406 cm^3
• Polarizability: 87.06532 Å^3
• Polar Surface Area: 236.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R508020

Rifampicin N-4’-Oxide is a metabolite of Rifampicin (R508000).

REFERENCES

• Gryaznova, N.S. et al.: Curr. Chemother. Immunother., Proc. Int. Congr. Chemother., 12, 984 (1982)
• Subbotina, N.A. et al.: Antibiotiki, 24, 590 (1982)