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

• ChemBase ID: 177778
• Molecular Formular: C19H37N5O7
• Molecular Mass: 447.52638
• Monoisotopic Mass: 447.26929855
• SMILES: CNC1C(O)C(OC2C(N)CC(N)C(OC3OC(=CCC3N)CN)C2O)OCC1(C)O
• Canonical SMILES: NCC1=CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N
• InChI: InChI=1S/C19H37N5O7/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/h3,9-18,24-27H,4-7,20-23H2,1-2H3
• InChIKey: URWAJWIAIPFPJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4,6-diamino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: sisomicin
• 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-glycero-hex-4-enopyranosyl-(1-4)]-2-deoxy- D-Streptamine; Antibiotic 66-40; Antibiotic 6640; Rickamicin; Sch 13475; Siseptin; Sisomicin

Database IDs

• CAS Number: 32385-11-8
• PubChem SID: 164233688
• PubChem CID: 5224

CALCULATED PROPERTIES

• Acid pKa: 12.548462
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -18.497313
• LogD (pH = 7.4): -11.9235935
• Log P: -4.3185678
• Molar Refractivity: 110.3207 cm^3
• Polarizability: 45.65683 Å^3
• Polar Surface Area: 213.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 80-93°C

Safety Information

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

DETAILS

Toronto Research Chemicals - S488500

Antibacterial. Gentamicin-like aminoglycoside antibiotic; has broad spectrum antibiotic activity.

REFERENCES

• Weinstein, M.J., et al.: J. Antibiot., 23, 551 (1970)
• Sculier, J.P., et al.: J. Antimicrob. Chemother., 9, 63 (1970)
• Noone, P., et al.: Drugs, 27, 548 (1970)