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Identification
NameG418
Accession NumberDB04263  (EXPT01586)
Typesmall molecule
Groupsexperimental
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
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number49863-47-0
WeightAverage: 496.5524
Monoisotopic: 496.27444352
Chemical FormulaC20H40N4O10
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassAmino Sugars
Direct parentAminocyclitol Glycosides
Alternative parentsOther Mixed Disaccharides; O-glycosyl Compounds; Aminocyclitols and Derivatives; Cyclohexanols; Oxanes; Tertiary Alcohols; 1,2-Diols; 1,2-Aminoalcohols; Dialkylamines; Polyamines; Acetals; Monoalkylamines
Substituentso-glycosyl compound; glycosyl compound; other mixed disaccharide; disaccharide; aminocyclitol derivative; cyclitol derivative; cyclohexanol; oxane; tertiary alcohol; cyclic alcohol; 1,2-aminoalcohol; 1,2-diol; secondary alcohol; secondary aliphatic amine; acetal; polyamine; secondary amine; ether; amine; alcohol; organonitrogen compound; primary aliphatic amine; primary amine
Classification descriptionThis compound belongs to the aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidially linked to a carbohydrate moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.9308
Blood Brain Barrier - 0.9911
Caco-2 permeable - 0.7061
P-glycoprotein substrate Substrate 0.6041
P-glycoprotein inhibitor I Non-inhibitor 0.6588
P-glycoprotein inhibitor II Non-inhibitor 0.9628
Renal organic cation transporter Non-inhibitor 0.9159
CYP450 2C9 substrate Non-substrate 0.8212
CYP450 2D6 substrate Non-substrate 0.8552
CYP450 3A4 substrate Substrate 0.5694
CYP450 1A2 substrate Non-inhibitor 0.9021
CYP450 2C9 substrate Non-inhibitor 0.9028
CYP450 2D6 substrate Non-inhibitor 0.929
CYP450 2C19 substrate Non-inhibitor 0.9209
CYP450 3A4 substrate Non-inhibitor 0.9578
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9114
Ames test Non AMES toxic 0.6652
Carcinogenicity Non-carcinogens 0.9575
Biodegradation Not ready biodegradable 0.9789
Rat acute toxicity 1.9026 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9973
hERG inhibition (predictor II) Non-inhibitor 0.9179
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility5.83e+01 g/lALOGPS
logP-2.4ALOGPS
logP-5.3ChemAxon
logS-0.93ALOGPS
pKa (strongest acidic)12.42ChemAxon
pKa (strongest basic)9.79ChemAxon
physiological charge4ChemAxon
hydrogen acceptor count14ChemAxon
hydrogen donor count10ChemAxon
polar surface area248.39ChemAxon
rotatable bond count6ChemAxon
refractivity114ChemAxon
polarizability50.77ChemAxon
number of rings3ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound46936936
PubChem Substance46505367
HETGET
WikipediaG418
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Ornithine decarboxylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ornithine decarboxylase P11926 Details

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 September 16, 2013 17:24