(7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1,3,5(28),9,19,21,25(29),26-octaene-6,23-dione

• ChemBase ID: 166124
• Molecular Formular: C45H62N4O11
• Molecular Mass: 834.99398
• Monoisotopic Mass: 834.44150882
• SMILES: c1(c2c3c4c(c1O)c(c(c(c4O)/C=N\N1CCN(CC1)C1CCCC1)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]([C@H](/C=C/O[C@@](O2)(C3=O)C)OC)C)O)C)O)C)O)C)/C)O)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N\N4CCN(CC4)C4CCCC4)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)O)C)O)C)O)C)/C
• InChI: InChI=1S/C45H62N4O11/c1-23-12-11-13-24(2)44(57)47-35-30(22-46-49-19-17-48(18-20-49)29-14-9-10-15-29)40(54)32-33(41(35)55)39(53)28(6)42-34(32)43(56)45(7,60-42)59-21-16-31(58-8)25(3)37(51)27(5)38(52)26(4)36(23)50/h11-13,16,21-23,25-27,29,31,36-38,50-55H,9-10,14-15,17-20H2,1-8H3,(H,47,57)/b12-11+,21-16+,24-13-,46-22?/t23-,25+,26+,27-,31-,36-,37+,38+,45-/m0/s1
• InChIKey: LPUNEQQTZOWCNO-AMEVKTJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1,3,5(28),9,19,21,25(29),26-octaene-6,23-dione
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,13,15,17,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1,3,5(28),9,19,21,25(29),26-octaene-6,23-dione
• Synonyms: 3-[[(4-Cyclopentyl-1-piperazinyl)imino]methyl]-25-O-deacetyl-rifamycin; 25-Deacetylrifapentine; L 14583; 25-Desacetyl Rifapentin

Database IDs

• CAS Number: 79039-56-8
• PubChem SID: 162260257
• PubChem CID: 46781115

CALCULATED PROPERTIES

• Acid pKa: 7.0085845
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): 1.9693471
• LogD (pH = 7.4): 3.2189128
• Log P: 3.1157591
• Molar Refractivity: 232.8445 cm^3
• Polarizability: 89.263535 Å^3
• Polar Surface Area: 214.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Brownish Red Solid
• Melting Point: 160-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288720

A metabolite of Rifapentine.

REFERENCES

• Kenny, M., et al.: Drug Metab. Rev., 12, 159 (1981)
• Battaglia, R., et al.: J. Antimicrob. Chemother., 26, 813 (1981)
• Ette, E., et al.: J. Clin. Pharmacol., 37, 486 (1981)
• Kerbusch, T., et al.: Br. J. Clin. Pharmacol., 56, 639 (1981)
• Langdon, G., et al