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

• ChemBase ID: 177547
• Molecular Formular: C47H64N4O12
• Molecular Mass: 877.03066
• Monoisotopic Mass: 876.45207351
• 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)OC(=O)C)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)OC(=O)C)C)O)C)O)C)/C
• InChI: InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23?/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
• InChIKey: WDZCUPBHRAEYDL-LYDPARFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-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-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[N-(4-cyclopentylpiperazin-1-yl)carboximidoyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-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-octaen-13-yl acetate
• Synonyms: 3-[[(4-Cyclopentyl-1-piperazinyl)imino]methyl]rifamycin; Antibiotic DL 473IT; Cyclopentylrifampicin; DL 473; KTC 1; MDL 473; Prifitin; Priftin; R 77-3; Rifamycin AF/ACPP; Rifapentin; Rifapentine

Database IDs

• CAS Number: 61379-65-5
• PubChem SID: 164233457
• PubChem CID: 66587073

CALCULATED PROPERTIES

• Acid pKa: 7.0085845
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 2.4104726
• LogD (pH = 7.4): 3.6600382
• Log P: 3.5568845
• Molar Refractivity: 241.996 cm^3
• Polarizability: 93.10482 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 179-180°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R508500

Semi-synthetic rifamycin. Antibacterial (tuberculostatic).

REFERENCES

• Arioli, V., et al.: J. Antibiot., 34, 1026 (1981)
• Neu, H.C., et al.: Antimicrob. Agents Chemother., 24, 457 (1981)
• Assandri, A., et al.: J. Antibiot., 37, 1066 (1981)
• Jarvis, B., et al.: Drugs, 56, 607 (1981)