(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-6,23,32-trioxo-1'-propyl-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: 166301
• Molecular Formular: C45H60N4O11
• Molecular Mass: 832.9781
• Monoisotopic Mass: 832.42585876
• 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)CCC)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: CCCN1CCC2(CC1)NC1=C3NC(=O)/C(=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@H]([C@H]([C@@H]([C@@H]([C@H](/C=C/O[C@@]4(C(=O)c5c(C1=N2)c(C3=O)c(O)c(c5O4)C)C)OC)C)OC(=O)C)C)O)/C
• InChI: InChI=1S/C45H60N4O11/c1-11-18-49-19-16-45(17-20-49)47-33-30-31-38(53)27(7)41-32(30)42(55)44(9,60-41)58-21-15-29(57-10)24(4)40(59-28(8)50)26(6)37(52)25(5)36(51)22(2)13-12-14-23(3)43(56)46-35(39(31)54)34(33)48-45/h12-15,21-22,24-26,29,36-37,40,48,51-53H,11,16-20H2,1-10H3,(H,46,56)/b13-12+,21-15+,23-14+/t22-,24+,25+,26+,29-,36-,37+,40+,44-/m0/s1
• InChIKey: OBIPQGBPCGPTRM-SXADLBPMSA-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-6,23,32-trioxo-1'-propyl-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-6,23,32-trioxo-1'-propyl-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-1-oxo-5'-propylrifamycin XIV; N-Desisobutyl-N-propyl Rifabutin

Database IDs

• CAS Number: 75903-10-5
• PubChem SID: 162260434
• PubChem CID: 46781138

CALCULATED PROPERTIES

• Acid pKa: 8.428866
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 2.0303385
• LogD (pH = 7.4): 3.7359757
• Log P: 3.9970746
• Molar Refractivity: 228.1729 cm^3
• Polarizability: 86.90253 Å^3
• Polar Surface Area: 205.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290080

A new class of rifamycins spiropiperidylrifamycins. Antibiotic.

REFERENCES

• Sanfilippo, A., et al.: J. Antibiotics, 33, 1193 (1980)