2-[(1S,2S,6S,7S,10S,11S,13R,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-ylidene]-6-methylhept-5-enoic acid; 2-[(2-hydroxyethyl)amino]ethan-1-ol

• ChemBase ID: 167106
• Molecular Formular: C35H59NO8
• Molecular Mass: 621.84486
• Monoisotopic Mass: 621.42406785
• SMILES: OCCNCCO.C1C([C@H]([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2([C@@H](C[C@H]1O)/C(=C(\CCC=C(C)C)/C(=O)O)/[C@@H](C2)OC(=O)C)C)C)C)C)O
• Canonical SMILES: CC(=O)O[C@@H]1C[C@]2([C@H](/C/1=C(/C(=O)O)\CCC=C(C)C)C[C@H]([C@@H]1[C@]2(C)CC[C@@H]2[C@]1(C)CCC([C@H]2C)O)O)C.OCCNCCO
• InChI: InChI=1S/C31H48O6.C4H11NO2/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32;6-3-1-5-2-4-7/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36);5-7H,1-4H2/b26-20-;/t18-,21-,22-,23?,24+,25+,27-,29-,30-,31-;/m0./s1
• InChIKey: OQZZCXRLEFBPLZ-DUDGZVDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,6S,7S,10S,11S,13R,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid; 2-[(2-hydroxyethyl)amino]ethan-1-ol
• IUPAC Traditional name: 2-[(1S,2S,6S,7S,10S,11S,13R,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid; diethanolamine
• Synonyms: (3,4α,8α,9β,11α,13α,14β,16β,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid compd. with 2,2'-Iminobis[ethanol]; 2,2'-Iminobis(ethanol) (3,4α,8α,9β,11α,13α,14β,16β,17Z)-16-(acetyloxy)- 3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oate; Diethanolamine Fusidate

Database IDs

• CAS Number: 16391-75-6
• PubChem SID: 162261239
• PubChem CID: 71315980

CALCULATED PROPERTIES

• Acid pKa: 4.664285
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.5278952
• LogD (pH = 7.4): 1.7501483
• Log P: 4.4219136
• Molar Refractivity: 144.1233 cm^3
• Polarizability: 56.94671 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D441880

A bacteriostatic antibiotic with similar activity and better absorption after oral administration (in animals) than the sodium salt of Fusidic Acid (F865500). Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G fac

REFERENCES

• Findon, G. et al.: Lab. Anim. Sci., 41, 462 (1991)
• Parsons, R.L. et al.: Curr. Chemother. Proc. Int. Cong. Chemother., 10, 384 (1991)