(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-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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: 177542
• Molecular Formular: C43H56N4O12
• Molecular Mass: 820.92434
• Monoisotopic Mass: 820.38947325
• 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)/C=N/N1CCN(CC1)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)/C=N/N1CCN(CC1)C
• InChI: InChI=1S/C43H56N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-51H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
• InChIKey: IHHAOHNZEKYBLG-WLSIYKJHSA-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-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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: 1,4-Dideoxy-1,4-dihydro-3-[(E)-[(4-methyl-1-piperazinyl)imino]methyl]-1,4-dioxo-Rifamycin; Rifampin Quinone; 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone 21-Acetate; NSC 145633; Rifaldazinequinone; Rifampicin Quinone

Database IDs

• CAS Number: 13983-13-6
• PubChem SID: 164233452
• PubChem CID: 9577278

CALCULATED PROPERTIES

• Acid pKa: 8.009439
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 1.7752482
• LogD (pH = 7.4): 2.4246907
• Log P: 2.4432068
• Molar Refractivity: 222.0666 cm^3
• Polarizability: 84.33632 Å^3
• Polar Surface Area: 213.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R508040

Rifampicin Quinone is a metabolite of Rifampicin (R508000). Rifampicin Quinone acts as an immunosuppressant unlike Rifampicin.

REFERENCES

• Gidoh, M. et al.: Nip. Rai Gak. Zas., 47, 110 (1978)
• Konrad, P. et al.: Clin. Immunol. Immunopathol., 46,162 (1978)
• Prasad, B. et al.: J. Pharmac. Biomed. Anal., 50, 475 (1978)