(2S)-4-amino-N-[(1R,2S,5S)-5-amino-4-{[(2S)-3-amino-6-{[(2-hydroxyethyl)amino]methyl}-3,4-dihydro-2H-pyran-2-yl]oxy}-2-{[(2R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide

• ChemBase ID: 176822
• Molecular Formular: C25H48N6O10
• Molecular Mass: 592.68282
• Monoisotopic Mass: 592.34319177
• SMILES: [C@@]1([C@@H](C([C@H](OC1)O[C@H]1[C@@H](C[C@@H](C(C1O)O[C@@H]1C(CC=C(O1)CNCCO)N)N)NC(=O)[C@H](CCN)O)O)NC)(O)C
• Canonical SMILES: NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)C(C([C@H]1O[C@H]1OC[C@]([C@@H](C1O)NC)(C)O)O)O[C@H]1OC(=CCC1N)CNCCO)O
• InChI: InChI=1S/C25H48N6O10/c1-25(37)11-38-24(18(35)21(25)29-2)41-20-15(31-22(36)16(33)5-6-26)9-14(28)19(17(20)34)40-23-13(27)4-3-12(39-23)10-30-7-8-32/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36)/t13?,14-,15+,16-,17?,18?,19?,20-,21+,23+,24+,25-/m0/s1
• InChIKey: IYDYFVUFSPQPPV-VDSDYXPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-N-[(1R,2S,5S)-5-amino-4-{[(2S)-3-amino-6-{[(2-hydroxyethyl)amino]methyl}-3,4-dihydro-2H-pyran-2-yl]oxy}-2-{[(2R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• IUPAC Traditional name: (2S)-4-amino-N-[(1R,2S,5S)-5-amino-4-{[(2S)-3-amino-6-{[(2-hydroxyethyl)amino]methyl}-3,4-dihydro-2H-pyran-2-yl]oxy}-2-{[(2R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
• Synonyms: O-2-Amino-2,3,4,6-tetradeoxy-6-[(2-hydroxyethyl)amino]-α-D-glycero-hex-4-enopyranosyl-(1→4)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine; ACHN 490; Plazomicin

Database IDs

• CAS Number: 1154757-24-0
• PubChem SID: 164232732
• PubChem CID: 71751715

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 12.484453
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -20.750345
• LogD (pH = 7.4): -14.220145
• Log P: -6.0995584
• Molar Refractivity: 145.0941 cm^3
• Polarizability: 59.245426 Å^3
• Polar Surface Area: 269.29 Å^2
• Rotatable Bonds: 13

DETAILS

Toronto Research Chemicals - P579500

Plazomicin is a neoglycoside antibiotic with activity against a broad range of Gram-positive and Gram-negive pathogens. Plazomicin showed potent in vitro activity against multidrug-resistant Klebsiella pneumoniae and Escherichia coli.

REFERENCES

• Endimiani, A. et al.: Antimicrob. Agents Chemother., 53, 4504 (2009)
• Landman, D. et al.: J. Antimicrob. Chemother., 65, 2123 (2009)
• Landman, D. et al.: J. Antimicrob. Chemother., 66, 332 (2009)