O-2-Amino-2,7-dideoxy-D-glycero-alpha-D-glucoheptopyranosyl-(1 fwdarw 4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1 fwarw 6))-2-deoxy-D-streptamin

Geneticin

HCID 123865
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Grundinformationen

CAS
49863-47-0
Standard-SMILES
CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](C)O)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O
InChIKey
BRZYSWJRSDMWLG-DJWUNRQOSA-N
Summenformel
C20H40N4O10
Durchschnittliche Molmasse
496,6 g/mol
Monoisotopische Masse
496,27444348

Überblick

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

Namen und Bezeichner

Bevorzugter Name
Geneticin
IUPAC
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-[(1R)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Lokaler Name
O-2-Amino-2,7-dideoxy-D-glycero-alpha-D-glucoheptopyranosyl-(1 fwdarw 4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1 fwarw 6))-2-deoxy-D-streptamin
Englischer Name
G418
Summenformel
C20H40N4O10
Molmasse
496.55

Namen und Synonyme

geneticin49863-47-0G418G 418A08F5XTI6GCHEBI:42768RefChem:558268antibiotic G 418antibiotic G-418G-418(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-[(1R)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol(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)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-((R)-1-hydroxyethyl)tetrahydro-2H-pyran-3,4-diol
Weitere Namen anzeigen
ANTIBIOTIC G418Aids114952Aids-114952G 418 DISULFATEGentamicin G-418Gentiomycin G-418
O-2-Amino-2,7-dideoxy-D-glycero-alpha-D-gluco-heptopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-D-streptamine(1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,7-dideoxy-D-glycero-alpha-D-gluco-heptopyranosideGETGeneticin disulfateGENETICIN(R)Geneticin disulfate saltUNII-A08F5XTI6GBRN 1669188

Datenbank-Bezeichner

CAS
49863-47-0
PubChem CID
123865
DTXSID
DTXSID10198129
ChEMBL
CHEMBL215226
UNII
A08F5XTI6G
Nikkaji
J147.239I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-5,8
Polarare Oberfläche (TPSA)
248 Ų
H-Brücken-Donoren
10
H-Brücken-Akzeptoren
14
Frei drehbare Bindungen
6
Schwere Atome
34

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Collision Cross Section210.14 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
193 °C · >193°C (dec.)
Siedepunkt
760.3 · 760.3±60.0 °C(Predicted)
Dichte
1.47 · 1.47±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: 50 mg/mL
Aggregatzustand
white powder

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk
3
risk_code
20/21/22
hazard_code
Xn
safety_code
22-24/25

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals.

Anbieter28 Anbieter

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
普洛药业股份有限公司/浙江横店普洛进出口有限公司+86-0571-87635730 +86-13588737631
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An aminoglycoside antibiotic produced by Micromonospora rhodorangea. It blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells.

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