Responsive image

Common name


Neomycin

IUPAC name


(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

SMILES


NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

Compound class


Anti-Bacterial Agents; Protein Synthesis Inhibitors; Aminoglycosides; Antibiotics; Blood and Blood Forming Organs; Respiratory System; Ophthalmologicals; Sensory Organs; Throat Preparations; Genito Urinary System and Sex Hormones; Alimentary Tract and Metabolism; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Stomatological Preparations; Dermatologicals; Blood Substitutes and Perfusion Solutions; Irrigating Solutions; Antiinfectives; Antibacterials for Intramammary Use; Antidiarrheals, Intestinal Anti-Inflammatory/antiinfective Agents; Antiinfectives and Antiseptics for Local Oral Treatment; Otologicals; Antibiotics for Topical Use; Antiinfectives and Antiseptics for Intrauterine Use; Ophthalmological and Otological Preparations; Aminoglycoside Antibacterials; Intestinal Antiinfectives;

Therapeutic area


Topical uses include treatment for superficial eye infections caused by susceptible bacteria (used in combination with other antiinfectives), treatment of otitis externa caused by susceptible bacteria, treatment or prevention of bacterial infections in skin lesions, and use as a continuous short-term irrigant or rinse to prevent bacteriuria and gram negative rod bacteremia in abacteriuric patients with indwelling catheters. May be used orally to treat hepatic encephalopathy, as a perioperative prophylactic agent, and as an adjunct to fluid and electrolyte replacement in the treatment of diarrhea caused to enteropathogenic E. coli (EPEC).

Common name


Neomycin

IUPAC name


(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

SMILES


NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

INCHI


InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

FORMULA


C23H46N6O13

Responsive image

Common name


Neomycin

IUPAC name


(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

Molecular weight


614.644

clogP


-9.134

clogS


5.789

HBond Acceptor


13

HBond Donor


19

Total Polar
Surface Area


353.11

Number of Rings


4

Rotatable Bond


9

Drug ID Common name Structure CAS SMILE Frequency
FDBF00059 (3S,4R)-tetrahydrofuran-3,4-diol Responsive image O1CC(C(C1)O)O 0.0048
FDBF00994 (2R,3R)-tetrahydrofuran-2,3-diol Responsive image OC1OCCC1O 0.0010
FDBF00995 (3R,5S)-5-(hydroxymethyl)tetrahydrofuran-3-ol Responsive image C(O)C1OCC(C1)O 0.0010
FDBF00996 (3R)-tetrahydrofuran-3-ol Responsive image O1CC(CC1)O 0.0014
4 , 1