7-[(1R,5S,6R)-6-[(2S)-2-[(2S)-2-aminopropanamido]propanamido](2,2,4,4-2H4)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid

• ChemBase ID: 159620
• Molecular Formular: C27H29F3N6O8S
• Molecular Mass: 654.6147696
• Monoisotopic Mass: 654.17196758
• SMILES: c1(c(cc2c(n1)n(cc(c2=O)C(=O)O)c1ccc(cc1F)F)F)N1C[C@H]2[C@H](C1)[C@@H]2NC(=O)[C@@H](NC(=O)[C@@H](N)C)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.Fc1ccc(c(c1)F)n1cc(C(=O)O)c(=O)c2c1nc(N1C[C@H]3[C@H](C1)[C@@H]3NC(=O)[C@@H](NC(=O)[C@@H](N)C)C)c(c2)F
• InChI: InChI=1S/C26H25F3N6O5.CH4O3S/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28;1-5(2,3)4/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40);1H3,(H,2,3,4)/t10-,11-,14-,15?,20+;/m0./s1
• InChIKey: CYETUYYEVKNSHZ-FBRYWZHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,5S,6R)-6-[(2S)-2-[(2S)-2-aminopropanamido]propanamido](2,2,4,4-^2H₄)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• IUPAC Traditional name: 7-[(1R,5S,6R)-6-[(2S)-2-[(2S)-2-aminopropanamido]propanamido](2,2,4,4-^2H₄)-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; methanesulfonic acid
• Synonyms: L-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninamide-d4 Methanesulfonate; L-Alanyl-N-[(1α,5α,6α)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-L-alaninamide-d4 Mesylate; CP 116517-d4; CP 116517-27-d4; Alatrofloxacin-d4 Mesylate

Database IDs

• PubChem SID: 162253755
• PubChem CID: 71313062

CALCULATED PROPERTIES

• Acid pKa: 5.4122415
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.0106379
• LogD (pH = 7.4): -0.8727407
• Log P: -0.8336422
• Molar Refractivity: 135.6352 cm^3
• Polarizability: 50.364147 Å^3
• Polar Surface Area: 157.96 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A511402

Labelled Alatrofloxacin (A511400). The parental prodrug of Trovafloxacin (T893000), on phagocytic, anti-inflammatory and immunomodulation events of human THP-1 monocytes.

REFERENCES

• Gladue, R., et al.: Antimicrob. Agent Chemother., 34, 1056 (1990)
• Bailly, S., et al.: Clin. Exp. Immunol., 85, 331 (1990)