(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-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 sodium

• ChemBase ID: 177545
• Molecular Formular: C37H47NNaO12
• Molecular Mass: 720.75835
• Monoisotopic Mass: 720.29959523
• SMILES: c1c2c(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.[Na]
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)cc(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.[Na]
• InChI: InChI=1S/C37H47NO12.Na/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41;/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46);/b11-10+,14-13+,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1
• InChIKey: URCDBMLCEGDNOK-NLYBMVFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-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 sodium
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-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 sodium
• Synonyms: 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione 21-Acetate Sodium Salt; Rifamastene; Rifocin; Tuborin; Rifamycin SV Sodium

Database IDs

• CAS Number: 14897-39-3
• PubChem SID: 164233455
• PubChem CID: 46782886

CALCULATED PROPERTIES

• Acid pKa: 7.0917516
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 4.1634398
• LogD (pH = 7.4): 3.6780498
• Log P: 4.1743436
• Molar Refractivity: 187.7982 cm^3
• Polarizability: 72.49382 Å^3
• Polar Surface Area: 201.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Red Solid
• Melting Point: >215°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R508200

Semi-synthetic antibiotic derived from Rifamycin S. Antibacterial. Potency >900 units (dry basis).

REFERENCES

• Sensi, et al.: Experientia, 16, 412 (1960)
• Bergamini, F., et al.: Arzneim.-Forsch., 15, 951 (1960)
• Mascherpa, P., et al.: Biochem. Pharmacol., 15, 200 (1960)