(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-formyl-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(29),2,4,9,19,21,25,27-octaen-13-yl acetate

• ChemBase ID: 179737
• Molecular Formular: C38H47NO13
• Molecular Mass: 725.77868
• Monoisotopic Mass: 725.30474057
• SMILES: c12c3O[C@@](C2=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)Nc2c(c(c1c(c2O)c(c3C)O)O)C=O)/C)C)O)C)O)C)OC(=O)C)C)OC)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)c(C=O)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/C38H47NO13/c1-16-11-10-12-17(2)37(48)39-28-23(15-40)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-16,18-20,24,29-30,34,42-46H,1-9H3,(H,39,48)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,24-,29-,30+,34+,38-/m0/s1
• InChIKey: BBNQHOMJRFAQBN-UPZFVJMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-formyl-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(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-formyl-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(29),2,4,9,19,21,25,27-octaen-13-yl acetate
• Synonyms: Rifaldehyde; 3-Formylrifamycin

Database IDs

• CAS Number: 13292-22-3
• PubChem SID: 164235647
• PubChem CID: 6438444

CALCULATED PROPERTIES

• Acid pKa: 6.904702
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 5.1701355
• LogD (pH = 7.4): 4.4850616
• Log P: 5.1868463
• Molar Refractivity: 194.3822 cm^3
• Polarizability: 74.42235 Å^3
• Polar Surface Area: 218.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of bacterial DNA-dependent RNA polymerase and viral; RNA-dependent DNA polymerase

Product Information

• Biological Source: Metab. of Streptomyces mediterranei*
• Application(s): Antibiotic

REFERENCES

• Maggi, N. et al., Antimicrob. Agents Chemother., 1965, 765-769, (metab, derivs)
• Netherlands Pat., 1966, Lepetit, 65 09 961; CA, 65, 5462c, (synth)
• Winsel, K. et al., Pharmazie, 1976, 31, 95-99, (metab)