(7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21E)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-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-octaene-6,23,32-trione

• ChemBase ID: 165460
• Molecular Formular: C44H60N4O10
• Molecular Mass: 804.968
• Monoisotopic Mass: 804.43094414
• 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)O
• 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)O)C)O)C)O)C)/C)CCN(CC5)CC(C)C
• InChI: InChI=1S/C44H60N4O10/c1-21(2)20-48-17-15-44(16-18-48)46-32-29-30-38(52)27(8)40-31(29)41(54)43(9,58-40)57-19-14-28(56-10)24(5)36(50)26(7)37(51)25(6)35(49)22(3)12-11-13-23(4)42(55)45-34(39(30)53)33(32)47-44/h11-14,19,21-22,24-26,28,35-37,47,49-52H,15-18,20H2,1-10H3,(H,45,55)/b12-11+,19-14+,23-13+/t22-,24+,25+,26-,28-,35-,36+,37+,43-/m0/s1
• InChIKey: SCGFWNINBXENQT-OSDOKOBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21E)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-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-octaene-6,23,32-trione
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21E)-2,13,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-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-octaene-6,23,32-trione
• Synonyms: 25-O-Deacetyl-1',4-didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxorifamycin XIV; 25-Hydroxy Rifabutin; 25-O-Deacetylrifabutin; 25-O-Desacetylrifabutin; Antibiotic LM 565; LM 565; 25-O-Deacetyl Rifabutin

Database IDs

• CAS Number: 100324-63-8
• PubChem SID: 162259593
• PubChem CID: 71315216

CALCULATED PROPERTIES

• Acid pKa: 7.946872
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): 1.708098
• LogD (pH = 7.4): 3.4124017
• Log P: 3.74525
• Molar Refractivity: 223.493 cm^3
• Polarizability: 84.89288 Å^3
• Polar Surface Area: 199.48 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Violet Solid
• Melting Point: 150-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D198980

A metabolite of Rifabutin (R505000), an antibacterial.

REFERENCES

• O’Brien, R.J., et al.: Infect. Dis., 9, 519 (1987)
• Anand, R., et al.: Antimicrob. Ag. Chemother., 32 (684 (1987)