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

• ChemBase ID: 165462
• Molecular Formular: C41H54N4O11
• Molecular Mass: 778.88766
• Monoisotopic Mass: 778.37890857
• 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)O)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)O)C)O)C)O)C)/C)/C=N/N1CCN(CC1)C
• InChI: InChI=1S/C41H54N4O11/c1-20-11-10-12-21(2)40(53)43-31-26(19-42-45-16-14-44(8)15-17-45)36(50)28-29(37(31)51)35(49)25(6)38-30(28)39(52)41(7,56-38)55-18-13-27(54-9)22(3)33(47)24(5)34(48)23(4)32(20)46/h10-13,18-20,22-24,27,32-34,46-49H,14-17H2,1-9H3,(H,43,53)/b11-10+,18-13+,21-12-,42-19+/t20-,22+,23+,24-,27-,32-,33+,34+,41-/m0/s1
• InChIKey: KMMWXQUVSZKIMQ-OACVHIRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaene-6,23,27,29-tetrone
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaene-6,23,27,29-tetrone
• Synonyms: 25-Deacetyl-1,4-didehydro-1,4-dideoxy-3-[[(4-methyl-1-piperazinyl)imino]methyl]-1,4-dioxo-Rifamycin; 25-Desacetylrifampin Quinone; Desacetyl Rifampicin Quinone

Database IDs

• CAS Number: 65110-92-1
• PubChem SID: 162259595
• PubChem CID: 71315218

CALCULATED PROPERTIES

• Acid pKa: 8.009439
• H Acceptors: 14
• H Donor: 5
• LogD (pH = 5.5): 1.3341228
• LogD (pH = 7.4): 1.9835653
• Log P: 2.0020814
• Molar Refractivity: 212.9151 cm^3
• Polarizability: 80.488335 Å^3
• Polar Surface Area: 207.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D198990

Desacetyl Rifampicin Quinone is an impurity of Rifampicin (R508000).

REFERENCES

• Wilson, W.L. et al.: J. Chrom., 144, 270 (1977)