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

• ChemBase ID: 3874
• Molecular Formular: C20H40N4O10
• Molecular Mass: 496.5524
• Monoisotopic Mass: 496.2744435
• 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](N)[C@H](O[C@H]2O[C@@H]([C@@H](C)O)[C@H](O)[C@@H](O)[C@@H]2N)[C@H]1O
• 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]1O[C@@H]([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+/m1/s1
• InChIKey: BRZYSWJRSDMWLG-IITTXYGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R)-2-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3S,4S,5R,6S)-3-amino-4,5-dihydroxy-6-[(1R)-1-hydroxyethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: (2R,3S,4S,5R)-2-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3S,4S,5R,6S)-3-amino-4,5-dihydroxy-6-[(1R)-1-hydroxyethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• Synonyms: G418

Database IDs

• CAS Number: 49863-47-0
• PubChem SID: 160967311; 46505367
• PubChem CID: 46936936

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.41
• LOG S: -0.93
• Solubility (Water): 5.83e+01 g/l

DETAILS

DrugBank - DB04263

• Drug Groups: experimental
• Description: G418 (also known as Geneticin) is an aminoglycoside antibiotic similar in structure to gentamicin B1. It is produced by Micromonospora rhodorangea. G418 blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells. Resistance to G418 is conferred by the neo gene from Tn5 encoding an aminoglycoside 3‘-phosphotransferase, APH 3‘ II. G418 is commonly used in laboratory research to select genetically engineered cells.
• External Links: Wikipedia