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

• ChemBase ID: 177538
• Molecular Formular: C46H64N4O12
• Molecular Mass: 865.01996
• Monoisotopic Mass: 864.45207351
• SMILES: c1(c2c(c3c(c1O)c1c(c(c3O)C)O[C@@](C1=O)(O/C=C/[C@@H]([C@@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C/C=C(\C(=O)N2)/C)C)O)C)O)C)OC(=O)C)C)OC)C)O)/C=N/N1CCN(CC1)CC(C)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)CC(C)C)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/C46H64N4O12/c1-23(2)22-49-16-18-50(19-17-49)47-21-31-36-41(56)34-33(40(31)55)35-43(29(8)39(34)54)62-46(10,44(35)57)60-20-15-32(59-11)26(5)42(61-30(9)51)28(7)38(53)27(6)37(52)24(3)13-12-14-25(4)45(58)48-36/h12-15,20-21,23-24,26-28,32,37-38,42,52-56H,16-19,22H2,1-11H3,(H,48,58)/b13-12+,20-15+,25-14-,47-21+/t24-,26-,27+,28+,32-,37-,38+,42+,46-/m0/s1
• InChIKey: LUSSUGVLLJCTQA-GFAIZCLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(2-methylpropyl)piperazin-1-yl]carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12S,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-[4-(2-methylpropyl)piperazin-1-yl]carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• Synonyms: 3-[[[4-(2-Methylpropyl)-1-piperazinyl]imino]methyl]rifamycin; Rifordin; Rifamdin

Database IDs

• CAS Number: 89499-17-2
• PubChem SID: 164233448
• PubChem CID: 71752079

CALCULATED PROPERTIES

• Acid pKa: 7.0033836
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): 2.3541543
• LogD (pH = 7.4): 3.5991
• Log P: 3.502137
• Molar Refractivity: 239.327 cm^3
• Polarizability: 91.98968 Å^3
• Polar Surface Area: 220.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R507900

A Rifamicyn derivative with therapeutic effect on pulmonary tuberculosis.

REFERENCES

• Gozalbes, R., et al.: J. Pharm. Pharmacol., 51, 111 (1999)
• Estrada, E., et al.: J. Med. Chem., 43, 1975 (1999)
• Gonzalez-Diaz, H., et al.: Chem. Res. Toxicol., 16, 1318 (1999)
• Garcia-Garcia, A., et al.: J. Antimicrob. Chemother., 53, 65 (1999)