(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-amino-2,15,17-trihydroxy-27-imino-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,29-trioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate

• ChemBase ID: 159986
• Molecular Formular: C37H47N3O11
• Molecular Mass: 709.78258
• Monoisotopic Mass: 709.32105934
• SMILES: C1(=C2C(=O)c3c(C1=N)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)N
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2C(=N)C(=C(C(=O)c2c(c3C)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)N
• InChI: InChI=1S/C37H47N3O11/c1-15-11-10-12-16(2)36(47)40-28-27(39)26(38)23-24(32(28)45)31(44)20(6)34-25(23)35(46)37(8,51-34)49-14-13-22(48-9)17(3)33(50-21(7)41)19(5)30(43)18(4)29(15)42/h10-15,17-19,22,29-30,33,38,42-44H,39H2,1-9H3,(H,40,47)/b11-10+,14-13+,16-12-,38-26?/t15-,17+,18+,19+,22-,29-,30+,33+,37-/m0/s1
• InChIKey: QIHXROBNYFPZNR-RAOJWDBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-amino-2,15,17-trihydroxy-27-imino-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,29-trioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-26-amino-2,15,17-trihydroxy-27-imino-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,29-trioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate
• Synonyms: 3-Amino-1,4-dideoxy-1,4-dihydro-4-imino-1-oxorifamycin; 3-Amino-4-iminorifamycin S; 3-Amino-4-deoxy-4-imino Rifamycin S

Database IDs

• CAS Number: 62041-01-4
• PubChem SID: 162254121
• PubChem CID: 20844286

CALCULATED PROPERTIES

• Acid pKa: 7.905233
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -0.86348104
• LogD (pH = 7.4): 0.6312805
• Log P: 1.1345006
• Molar Refractivity: 201.814 cm^3
• Polarizability: 72.141235 Å^3
• Polar Surface Area: 227.79 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A603960

A Rifamycin (R508200) derivative as antibacterial agent.

REFERENCES

• Cellai, L., et al.: Eur. J. Med. Chem., 24, 105 (1989)
• Bartolucci, C., et al.: Pharm. Pharmacol. Lett., 3, 1 (1989)
• Lounis, N., et al.: Curr. Pharm. Des., 10, 3229 (1989)