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Identification
Name G418
Accession Number DB04263 (EXPT01586)
Type small molecule
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.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Amebicides
  • Coccidiostats
CAS number 49863-47-0
Weight Average: 496.5524
Monoisotopic: 496.27444352
Chemical Formula C20H40N4O10
InChI Key InChIKey=BRZYSWJRSDMWLG-IITTXYGFSA-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
Plain Text
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
SMILES
CN[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@@H]([C@@H](C)O)[C@H](O)[C@@H](O)[C@@H]3N)[C@H]2O)OC[C@]1(C)O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 5.83e+01 g/l ALOGPS
logP -2.4 ALOGPS
logP -5.3 ChemAxon
logS -0.93 ALOGPS
pKa (strongest acidic) 12.42 ChemAxon
pKa (strongest basic) 9.79 ChemAxon
physiological charge 4 ChemAxon
hydrogen acceptor count 14 ChemAxon
hydrogen donor count 10 ChemAxon
polar surface area 248.39 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 114 ChemAxon
polarizability 50.77 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 46936936 Link_out
PubChem Substance 46505367 Link_out
HET GET Link_out
Wikipedia http://en.wikipedia.org/wiki/G418 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Ornithine decarboxylase

Pharmacological action: unknown
Organism class: human
UniProt ID: P11926 Link_out
Gene: ODC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:23