(7S,9E,11S,12R,13R,14R,15R,16R,17S,18S,19E,21Z,24Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23,36-trioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,24,26(34),28,30,32-undecaen-13-yl acetate

• ChemBase ID: 165696
• Molecular Formular: C43H49N3O11
• Molecular Mass: 783.86266
• Monoisotopic Mass: 783.3367094
• SMILES: c12c3c4c(/C(=N/C(=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@]5(Oc(c(c2O)C)c3C5=O)C)OC)C)OC(=O)C)C)O)C)O)C)/C)/C1=O)n1c(n4)cc(cc1)C
• Canonical SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(c(c3C)O)C(=O)/C(=N\C(=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)/c1c2nc2n1ccc(c2)C
• InChI: InChI=1S/C43H49N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-50H,1-10H3/b12-11+,17-15+,21-13-,45-33-/t20-,22+,23+,24+,27-,35-,36+,39-,43-/m0/s1
• InChIKey: UIQBVIBLPYSOHX-GHSIUBAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9E,11S,12R,13R,14R,15R,16R,17S,18S,19E,21Z,24Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23,36-trioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1^4,^7.0^5,^3^5.0^2^6,^3^4.0^2^7,^3^2]heptatriaconta-1(35),2,4,9,19,21,24,26(34),28,30,32-undecaen-13-yl acetate
• IUPAC Traditional name: (7S,9E,11S,12R,13R,14R,15R,16R,17S,18S,19E,21Z,24Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23,36-trioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1^4,^7.0^5,^3^5.0^2^6,^3^4.0^2^7,^3^2]heptatriaconta-1(35),2,4,9,19,21,24,26(34),28,30,32-undecaen-13-yl acetate
• Synonyms: [2S-(2R*,16Z,18E,20R*,21R*,22S*,23S*,24S*,25R*,26S*,27R*,28E)]-25-(Acetyloxy)-5,21,23-trihydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-6H-27-(epoxypentadeca[1,11,13]trienonitrilo)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,6,15(2H)-trione; Dehydro Rifaximin

Database IDs

• CAS Number: 80621-76-7
• PubChem SID: 162259829
• PubChem CID: 71315344

CALCULATED PROPERTIES

• Acid pKa: 8.034503
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 5.27972
• LogD (pH = 7.4): 5.214433
• Log P: 5.3044906
• Molar Refractivity: 213.4643 cm^3
• Polarizability: 82.039696 Å^3
• Polar Surface Area: 195.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230300

Rifaximin (R509500) impurity.

REFERENCES

• Cellai, L., et al.: Mol. Pharmacol., 27, 103 (1985)