(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-[2-(2H3)methyl(3,3,3-2H3)propyl]-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.14,7.05,31.026,30]tritriacontane-28,4'-piperidin]-1(31),2,4,9,19,21,25,29-octaen-13-yl acetate

• ChemBase ID: 177537
• Molecular Formular: C46H62N4O11
• Molecular Mass: 847.00468
• Monoisotopic Mass: 846.44150882
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(/C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)c3c(C2=O)c(c(c2c3C(=O)[C@@](O/C=C/[C@@H]([C@H]1C)OC)(O2)C)C)O)\C)C)O)C)O)C)OC(=O)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2C4=NC5(NC4=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)CCN(CC5)CC(C)C
• InChI: InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14+/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
• InChIKey: ATEBXHFBFRCZMA-NYGPAKPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-[2-(^2H₃)methyl(3,3,3-^2H₃)propyl]-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1^4,^7.0^5,^3^1.0^2^6,^3^0]tritriacontane-28,4'-piperidin]-1(31),2,4,9,19,21,25,29-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-[2-(^2H₃)methyl(3,3,3-^2H₃)propyl]-6,23,32-trioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1^4,^7.0^5,^3^1.0^2^6,^3^0]tritriacontane-28,4'-piperidin]-1(31),2,4,9,19,21,25,29-octaen-13-yl acetate
• Synonyms: 1',4-Didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxorifamycin XIV-d6; Ansatipine-d6; Ansamycin-d6; Antibiotic LM 427-d6; LM 427-d6; Mycobutin-d6; Rifabutine; Rifabutin-d6

Database IDs

• PubChem SID: 164233447
• PubChem CID: 71752078

CALCULATED PROPERTIES

• Acid pKa: 7.946872
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 2.1492233
• LogD (pH = 7.4): 3.853527
• Log P: 4.1863756
• Molar Refractivity: 232.6445 cm^3
• Polarizability: 88.737564 Å^3
• Polar Surface Area: 205.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R505002

Labelled Rifabutin (R505000). Semisynthetic derivative of Rifamycin S that inhibits nucleic acid synthesis. An antibacterial (tuberculostatic).

REFERENCES

• O’Brien, R.J., et al.: Infect. Dis., 9, 519 (1987)
• Anand, R., et al.: Antimicrob. AG. Chemother., 32 (684 (1987)
• Skinner, M.H., et al.: Antimicrob. Agent Chemother., 33, 1237 (1987)