4-O-(2-アミノ-2,7-ジデオキシ-α-D-glycero-D-gluco-ヘプトピラノシル)-6-O-[4-C-メチル-3-(メチルアミノ)-3-デオキシ-β-L-アラビノピラノシル]-2-デオキシ-D-ストレプタミン

Geneticin

HCID 123865

基本情報

CAS: 49863-47-0
標準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
分子式: C20H40N4O10
平均分子量: 496.6 g/mol
単同位体質量: 496.27444348

概要

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.

名称と識別子

優先名称: 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
現地名: 4-O-(2-アミノ-2,7-ジデオキシ-α-D-glycero-D-gluco-ヘプトピラノシル)-6-O-[4-C-メチル-3-(メチルアミノ)-3-デオキシ-β-L-アラビノピラノシル]-2-デオキシ-D-ストレプタミン
英語名: G418
分子式: C20H40N4O10
分子量: 496.55

名称と別名

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

名称をさらに表示

ゲネチシンゲンタマイシンG-4184-O-(2-アミノ-2,7-ジデオキシ-α-D-glycero-D-gluco-ヘプトピラノシル)-6-O-[4-C-メチル-3-(メチルアミノ)-3-デオキシ-β-L-アラビノピラノシル]-2-デオキシ-D-ストレプタミンゲンタミシンG-418ゲンチオマイシンG-418抗生物質G-418ジェネティシン(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-ジアミノ-3-{[(2S,3R,4R,5S,6R)-3-アミノ-4,5-ジヒドロキシ-6-[(1R)-1-ヒドロキシエチル]オキサン-2-イル]オキシ}-2-ヒドロキシシクロヘキシル]オキシ}-5-メチル-4-(メチルアミノ)オキサン-3,5-ジオール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

データベース識別子

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

物性

構造計算による物性

XLogP: -5.8
極性表面積: 248 Å²
水素結合供与体数: 10
水素結合受容体数: 14
回転可能結合数: 6
重原子数: 34
形式電荷: 0
複雑度: 681

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Collision Cross Section210.14 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 193 °C · >193°C (dec.)
沸点: 760.3 · 760.3±60.0 °C(Predicted)
比重(密度): 1.47 · 1.47±0.1 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: 50 mg/mL
外見: 白い粉
酸解離定数(Pka): 13.29 · 13.29±0.70(Predicted)
色: ホワイトからオフホワイト
安定性: 吸湿性

安全と法規制

安全データ

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

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

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.

サプライヤー28 社

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]

補足説明

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