3-ヒドロキシ-N-[(2Z,5R,6S,9S,10S,11R)-10-ヒドロキシ-5,11-ジメチル-2-(1-メチルプロピリデン)-3,7,12-トリオキソ-9-(3-ピリジルメチル)-1,4-ジオキサ-8-アザシクロドデカ-6-イル]-2-ピリジンカルボアミド
3-Hydroxy-N-((2Z,5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl)-2-pyridinecarboxamide
基本情報
- CAS
18791-21-4- 標準SMILES
CC/C(C)=C1\OC(=O)[C@H](C)[C@H](O)[C@H](Cc2cccnc2)NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC1=O- InChIKey
WHIKSLGSXKIHCA-IGCCMALHSA-N- 分子式
- C27H32N4O8
- 平均分子量
- 540.6 g/mol
- 単同位体質量
- 540.22201399
概要
extract of Streptomyces
名称と識別子
- 優先名称
- 3-Hydroxy-N-((2Z,5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl)-2-pyridinecarboxamide
- IUPAC
- N-[(2Z,5R,6S,9S,10S,11R)-2-butan-2-ylidene-10-hydroxy-5,11-dimethyl-3,7,12-trioxo-9-(pyridin-3-ylmethyl)-1,4-dioxa-8-azacyclododec-6-yl]-3-hydroxypyridine-2-carboxamide
- 現地名
- 3-ヒドロキシ-N-[(2Z,5R,6S,9S,10S,11R)-10-ヒドロキシ-5,11-ジメチル-2-(1-メチルプロピリデン)-3,7,12-トリオキソ-9-(3-ピリジルメチル)-1,4-ジオキサ-8-アザシクロドデカ-6-イル]-2-ピリジンカルボアミド
- 英語名
- Pyridomycin
- 分子式
- C27H32N4O8
- 分子量
- 540.57
名称と別名
Pyridomycin18791-21-4ZTB2215O45DTXSID001099046NSC-2461343-Hydroxy-N-((2Z,5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl)-2-pyridinecarboxamide3-Hydroxy-N-[(2Z,5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl]-2-pyridinecarboxamideRefChem:198304DTXCID301838243N-((2Z,5R,6S,9S,10R,11R)-2-butan-2-ylidene-10-hydroxy-5,11-dimethyl-3,7,12-trioxo-9-(pyridin-3-ylmethyl)-1,4-dioxa-8-azacyclododec-6-yl)-3-hydroxypyridine-2-carboxamideErizomycinN-[(2Z,5R,6S,9S,10S,11R)-2-butan-2-ylidene-10-hydroxy-5,11-dimethyl-3,7,12-trioxo-9-(pyridin-3-ylmethyl)-1,4-dioxa-8-azacyclododec-6-yl]-3-hydroxypyridine-2-carboxamide
名称をさらに表示
3-ヒドロキシ-N-[(2Z,5R,6S,9S,10S,11R)-10-ヒドロキシ-5,11-ジメチル-2-(1-メチルプロピリデン)-3,7,12-トリオキソ-9-(3-ピリジルメチル)-1,4-ジオキサ-8-アザシクロドデカ-6-イル]-2-ピリジンカルボアミド
物性
構造計算による物性
- XLogP
- 2.8
- 極性表面積
- 177 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 10
- 回転可能結合数
- 5
- 重原子数
- 39
- 形式電荷
- 0
- 複雑度
- 941
物理化学的性質
- 融点
- 222 ° · 222°
- 沸点
- 616.01 °C · 616.01°C (rough estimate)
- 比重(密度)
- 1.3105 · 1.3105 (rough estimate)
- 屈折率
- 1.6 · 1.6000 (estimate)
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- 酸解離定数(Pka)
- 11.54 · 11.54±0.70(Predicted)
化学と産業
応用分野
説明Pyridomycin is a structurally unusual antimycobacterial cyclodepsipeptide whose composition includes two rare moieties: 3-(3-pyridyl)-L-alanine and 2-hydroxy-3-methylpent-2-enoic acid. It inhibits NADH-dependent enoyl (Acyl-Carrier-Protein) reductase InhA, preventing mycolic acid synthesis in M. tuberculosis, including isoniazid-resistant strains (MICs = 0.31-0.63 μg/ml).
使用Pyridomycin is a potent antibiotic active against mycobacteria and some Gram negative bacteria, originally isolated from Streptomyces abidoflavus by Umezawa group at the NIH Japan in 1953, and since isolated from different species and published under several names. The unusual 12-membered macrocyclic depsipeptide comprises three unique sub-units incorporating two substituted pyridines. Pyridomycin is thought to target NADH-dependent enoyl (acyl-carrier-protein) reductase InhA. Recent reports of activity against isoniazid-resistant mycobacteria has seen pyridomycin identified as a potential lead for new generation antibiotics.
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