2-[(4,6-diamino-3-{[3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol

• ChemBase ID: 169614
• Molecular Formular: C19H39N5O7
• Molecular Mass: 449.54226
• Monoisotopic Mass: 449.28494861
• SMILES: C1CC(C(OC1CN)OC1C(C(C(CC1N)N)OC1C(C(C(CO1)(O)C)NC)O)O)N
• Canonical SMILES: NCC1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N
• InChI: InChI=1S/C19H39N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h8-18,24-27H,3-7,20-23H2,1-2H3
• InChIKey: VEGXETMJINRLTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4,6-diamino-3-{[3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: 2-[(4,6-diamino-3-{[3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• Synonyms: O-3-Deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl-(1-4)]-2-deoxy-D-streptamine Pentaacetate Salt; Gentamicin D Acetate; Gentamycin C1a Acetate; Gentamicin C3 Acetate; Gentamicin C1a Pentaacetate Salt

Database IDs

• CAS Number: 26098-04-4
• PubChem SID: 162263746
• PubChem CID: 582362

CALCULATED PROPERTIES

• Acid pKa: 12.5486965
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -18.30707
• LogD (pH = 7.4): -12.23723
• Log P: -3.986311
• Molar Refractivity: 108.8273 cm^3
• Polarizability: 45.905064 Å^3
• Polar Surface Area: 213.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Beige Solid
• Melting Point: 112-115°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G360590

Antibacterial.

REFERENCES

• Holt, H.A., et al.: J. Antimicrob. Chemother., 34, 747 (1994)
• Wilschanski, M., et al.: Am. J. Respir. Crit. Care Med., 161, 860 (1994)