(3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-[(1S)-1-hydroxyethyl]oxane-3,4-diol

• ChemBase ID: 127508
• Molecular Formular: C20H40N4O10
• Molecular Mass: 496.5524
• Monoisotopic Mass: 496.2744435
• SMILES: O[C@H]1[C@H](O)[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)OC1[C@@H](O)C
• Canonical SMILES: CN[C@@H]1[C@@H](O)[C@H](OC[C@]1(C)O)O[C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@H]1OC([C@@H](O)C)[C@H]([C@@H]([C@H]1N)O)O)N
• InChI: InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7-,8+,9+,10+,11-,12-,13+,14?,15+,16-,17+,18+,19+,20-/m0/s1
• InChIKey: BRZYSWJRSDMWLG-NQRKCNNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-[(1S)-1-hydroxyethyl]oxane-3,4-diol
• IUPAC Traditional name: (3S,4R,5R,6S)-5-amino-6-{[(1R,2S,3S,4R,6S)-4,6-diamino-3-{[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-2-[(1S)-1-hydroxyethyl]oxane-3,4-diol
• Synonyms: Geneticin; O-2-Amino-2,7-didesoxy-D-glycero-α-D-gluco-heptopyranosyl-(1→4)-O-(3-desoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl- (1→6))-D-streptamin; G418

Database IDs

• CAS Number: 49863-47-0
• PubChem SID: 162221827
• PubChem CID: 123865; 71308205
• CHEMBL: 215226
• Chemspider ID: 21106441
• DrugBank ID: DB04263
• Wikipedia Title: G418

CALCULATED PROPERTIES

• Acid pKa: 12.420779
• H Acceptors: 14
• H Donor: 10
• LogD (pH = 5.5): -16.208046
• LogD (pH = 7.4): -10.701025
• Log P: -5.3008466
• Molar Refractivity: 114.0036 cm^3
• Polarizability: 48.22068 Å^3
• Polar Surface Area: 248.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 50 mg/mL in water

Safety Information

• Safety Statements: R