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Identification
NameGeneticin
Accession NumberDB04263  (EXPT01586)
TypeSmall Molecule
GroupsExperimental
Description

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

Structure
Thumb
SynonymsNot Available
External Identifiers
  • Antibiotic G 418
  • Antibiotic g-418
  • G-418
  • G418
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIA08F5XTI6G
CAS number49863-47-0
WeightAverage: 496.5524
Monoisotopic: 496.27444352
Chemical FormulaC20H40N4O10
InChI KeyBRZYSWJRSDMWLG-DJWUNRQOSA-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,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-[(1R)-1-hydroxyethyl]oxane-3,4-diol
SMILES
[H][C@](C)(O)[C@@]1([H])O[C@]([H])(O[C@]2([H])[C@@]([H])(N)C[C@@]([H])(N)[C@]([H])(O[C@@]3([H])OC[C@](C)(O)[C@]([H])(NC)[C@@]3([H])O)[C@@]2([H])O)[C@]([H])(N)[C@@]([H])(O)[C@]1([H])O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption-0.9308
Blood Brain Barrier-0.9911
Caco-2 permeable-0.7061
P-glycoprotein substrateSubstrate0.6041
P-glycoprotein inhibitor INon-inhibitor0.6588
P-glycoprotein inhibitor IINon-inhibitor0.9628
Renal organic cation transporterNon-inhibitor0.9159
CYP450 2C9 substrateNon-substrate0.8212
CYP450 2D6 substrateNon-substrate0.8552
CYP450 3A4 substrateSubstrate0.5694
CYP450 1A2 substrateNon-inhibitor0.9021
CYP450 2C9 inhibitorNon-inhibitor0.9028
CYP450 2D6 inhibitorNon-inhibitor0.929
CYP450 2C19 inhibitorNon-inhibitor0.9209
CYP450 3A4 inhibitorNon-inhibitor0.9578
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9114
Ames testNon AMES toxic0.6652
CarcinogenicityNon-carcinogens0.9575
BiodegradationNot ready biodegradable0.9789
Rat acute toxicity1.9026 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9973
hERG inhibition (predictor II)Non-inhibitor0.9179
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility58.3 mg/mLALOGPS
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 Area248.39 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity114 m3·mol-1ChemAxon
Polarizability50.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
Gene Name:
ODC1
Uniprot ID:
P11926
Molecular Weight:
51147.73 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on May 10, 2016 15:03