(11R)-11-C-(6-アミノ-9H-プリン-9-イル)-2,6:8,11-ジアンヒドロ-10-O-メチル-4-O-[(E)-1-オキソ-2-(ヒドロキシメチル)-2-ブテニル]-7-デオキシ-α-L-ido-D-lyxo-5-ウンデクロ-5,9-ピラノソン酸メチル
Herbicidin A
基本情報
- CAS
55353-31-6- 標準SMILES
C/C=C(\CO)C(=O)O[C@H]1[C@H](O)[C@@H](C(=O)OC)O[C@@H]2C[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OC)[C@H]3O[C@]21O- InChIKey
LOWKANMKNQBRPJ-MRAUHCMASA-N- 分子式
- C23H29N5O11
- 平均分子量
- 551.5 g/mol
- 単同位体質量
- 551.18635676
概要
Herbicidin A has been reported in Streptomyces and Streptomyces scopuliridis with data available.
名称と識別子
- 優先名称
- Herbicidin A
- IUPAC
- methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12-dihydroxy-13-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-4-methoxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate
- 現地名
- (11R)-11-C-(6-アミノ-9H-プリン-9-イル)-2,6:8,11-ジアンヒドロ-10-O-メチル-4-O-[(E)-1-オキソ-2-(ヒドロキシメチル)-2-ブテニル]-7-デオキシ-α-L-ido-D-lyxo-5-ウンデクロ-5,9-ピラノソン酸メチル
- 英語名
- Herbicidin A
- 分子式
- C23H29N5O11
- 分子量
- 551.5
名称と別名
Herbicidin A55353-31-6Herbicidin-Aalpha-L-ido-D-lyxo-5-Undeculo-5,9-pyranosonic acid, 11-C-(6-amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-10-O-methyl-, methyl ester, 4-(2-(hydroxymethyl)-2-butenoate), (4(E),11R)-methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12-dihydroxy-13-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-4-methoxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylatemethyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12-dihydroxy-13-((E)-2-(hydroxymethyl)but-2-enoyl)oxy-4-methoxy-2,6,10-trioxatricyclo(7.4.0.03,7)tridecane-11-carboxylateMethyl (1S,3R,4S,5R,7R,9R,11S,12S,13S)-5-(6-amino-9H-purin-9-yl)-1,12-dihydroxy-13-(((2E)-2-(hydroxymethyl)but-2-enoyl)oxy)-4-methoxy-2,6,10-trioxatricyclo(7.4.0.0,)tridecane-11-carboxylic acidMethyl (1S,3R,4S,5R,7R,9R,11S,12S,13S)-5-(6-amino-9H-purin-9-yl)-1,12-dihydroxy-13-{[(2E)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-methoxy-2,6,10-trioxatricyclo[7.4.0.0,]tridecane-11-carboxylic acidRefChem:145768Methyl (2R,3R,3aS,4aR,5S,6S,7S,8aR,9aR)-2-(6-amino-9H-purin-9-yl)-4a,6-dihydroxy-5-(((E)-2-(hydroxymethyl)but-2-enoyl)oxy)-3-methoxydecahydrofuro[3,2-b]pyrano[2,3-e]pyran-7-carboxylate
物性
構造計算による物性
- XLogP
- -1.8
- 極性表面積
- 220 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 15
- 回転可能結合数
- 8
- 重原子数
- 39
- 形式電荷
- 0
- 複雑度
- 973
物理化学的性質
- 沸点
- 826.5 · 826.5±75.0 °C(Predicted)
- 比重(密度)
- 1.78 · 1.78±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- 外見
- A solid
- 酸解離定数(Pka)
- 10.17 · 10.17±0.70(Predicted)
化学と産業
応用分野
説明Herbicidin A is an adenine nucleoside antibiotic originally isolated from S. saganonensis that exhibits herbicidal activity, particularly against dicotyledonous plants. It prevents rice seed germination (MIC = 6.25 μg/ml) and completely protects young rice plants from X. oryzae-induced leaf blight when applied at 100 ppm. In HEK293 cells, herbicidin A inhibits TNF-α-induced NF-κB activity and induces cytotoxicity (IC50s = 1.8 and 2.7 μM, respectively).
使用Herbicidin A is the major analogue of a family of adenosine nucleosides containing a complex tricyclic saccharide originally isolated from Streptomyces saganonensis, reported by researchers at Sankyo in 1976. Hebicidin A is a potent herbicide with selective activity against dicotyledonous plants. The mode of action and broader pharmacology of herbicidin A has received little attention due to its restricted availability.
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