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

• ChemBase ID: 165810
• Molecular Formular: C42H56N4O12
• Molecular Mass: 808.91364
• Monoisotopic Mass: 808.38947325
• 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/N1CCNCC1
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCNCC4)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/C42H56N4O12/c1-20-11-10-12-21(2)41(54)45-32-27(19-44-46-16-14-43-15-17-46)36(51)29-30(37(32)52)35(50)25(6)39-31(29)40(53)42(8,58-39)56-18-13-28(55-9)22(3)38(57-26(7)47)24(5)34(49)23(4)33(20)48/h10-13,18-20,22-24,28,33-34,38,43,48-52H,14-17H2,1-9H3,(H,45,54)/b11-10+,18-13+,21-12-,44-19+/t20-,22+,23+,24+,28-,33-,34+,38+,42-/m0/s1
• InChIKey: FKKVFHDDYXJFFL-VIVOQTQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[(E)-N-(piperazin-1-yl)carboximidoyl]-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-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[(E)-N-(piperazin-1-yl)carboximidoyl]-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-13-yl acetate
• Synonyms: 3-[(1-Piperazinylimino)methyl]-rifamycin; 3-Piperazinoiminomethyl Rifamycin SV; 4-N-Demethylrifampicin; AF/AP; Demethylrifampicin; N-Demethylrifampicin; N-Demethylrifampin; NSC 143416; Rifampicin AF/AP; N-Demethyl Rifampin

Database IDs

• CAS Number: 13292-45-0
• PubChem SID: 162259943
• PubChem CID: 6436631

CALCULATED PROPERTIES

• Acid pKa: 7.018918
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): 0.8200904
• LogD (pH = 7.4): 2.068037
• Log P: 1.9577157
• Molar Refractivity: 220.2881 cm^3
• Polarizability: 84.6442 Å^3
• Polar Surface Area: 228.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D231250

N-Demethyl Rifampin is a metabolite of Rifampicin (R508000).

REFERENCES

• Marsili, L., et al.: J. Antibiot., 37, 1209 (1984)
• Nikaido, H., et al.: Antimicrob. Ag. Chemother., 37, 1393 (1984)
• Piddock, L., et al.: J. Antimicrob. Chemother., 45, 159 (1984)