ニューモカンジンB0

(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaone

HCID 5742645

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 135575-42-7
標準SMILES: CCC(C)CC(C)CCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@H]([C@H](O)CC(N)=O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O
InChIKey: DQXPFAADCTZLNL-ZESADUFFSA-N
分子式: C50H80N8O17
平均分子量: 1,065.2 g/mol

名称と識別子

優先名称: (2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaone
IUPAC: N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide
現地名: ニューモカンジンB0
英語名: Pneumocandin B0
分子式: C50H80N8O17
分子量: 1065.22

名称と別名

(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[2-Carbamoyl-1(R)-hydroxyethyl]-23-[1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl]-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-[1(R)-hydroxyethyl]perhydrodipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine-5,8,14,19,22,25-hexaone(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-(2-Carbamoyl-1(R)-hydroxyethyl)-23-(1(S),2(S)-dihydroxy-2-(4-hydroxyphenyl)ethyl)-9-(10,12-dimethyltetradecanamido)-2,11,12,15-tetrahydroxy-6-(1(R)-hydroxyethyl)perhydrodipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacycloheneicosine-5,8,14,19,22,25-hexaoneRefChem:397684629-746-0Pneumocandin BoCHEMBL269311C50H80N8O17N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-Amino-1-hydroxy-3-oxopropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamideHydroxy EchinocandinSCHEMBL8444763DQXPFAADCTZLNL-ZESADUFFSA-NGLXC-20110

名称をさらに表示

ニューモカンジンB0ノイモカンジンB0N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-2-カルバモイル-1-ヒドロキシエチル]-6-[(1S,2S)-1,2-ジヒドロキシ-2-(4-ヒドロキシフェニル)エチル]-11,20,21,25-テトラヒドロキシ-15-[(1R)-1-ヒドロキシエチル]-2,5,8,14,17,23-ヘキサオキソ-1,4,7,13,16,22-ヘキサアザトリシクロ[22.3.0.09,13]ヘプタコサン-18-イル]-10,12-ジメチルテトラデカンアミドシクロ[L-Thr-4β-ヒドロキシ-L-Pro-[(4S)-4-ヒドロキシ-4-(4-ヒドロキシフェニル)-L-Thr-]-[(3R)-3-ヒドロキシ-L-Gln-]-3β-ヒドロキシ-L-Pro-[(4R,5R)-4,5-ジヒドロキシ-N2-(10,12-ジメチル-1-オキソテトラデシル)-L-Orn*-]]CFAPneumocardin B0Caspofungin PneuMocandin B0 IMpurityCS-492L-688786CFA/ CBR01Novocontin B0PneumocandinBoneumocandin B0

EX-A1768BDBM50043897FP76367PD11815310,12-Dimethyl-tetradecanoic acid [3-(2-carbamoyl-1-hydroxy-ethyl)-6-[1,2-dihydroxy-2-(4-hydroxy-phenyl)-ethyl]-11,20,21,25-tetrahydroxy-15-(1-hydroxy-ethyl)-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.0*9,13*]heptacos-18-yl]-amide1N-[20-(2-carbamoyl-1-hydroxyethyl)-23-[1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-(1-hydroxyethyl)-5,8,14,19,22,25-hexaoxoperhydrodipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamN-((2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-((R)-3-amino-1-hydroxy-3-oxopropyl)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6-((R)-1-hydroxyethyl)-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)-10,12-dimethyltetradecanamideN-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S)-3-[(1R)-3-amino-1-hydroxy-3-oxo-propyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyl-tetradecanamide

データベース識別子

CAS: 135575-42-7
PubChem CID: 5742645
ChEMBL: CHEMBL269311
Nikkaji: J613.168I

物性

構造計算による物性

XLogP: 0.5
極性表面積: 411 Å²
水素結合供与体数: 15
水素結合受容体数: 17
回転可能結合数: 20
重原子数: 75
形式電荷: 0
複雑度: 1,930

物理化学的性質

融点: 230 °C · >230°C (dec.)
沸点: 1442.9 · 1442.9±65.0 °C(Predicted)
比重(密度): 1.41 · 1.41±0.1 g/cm3(Predicted)
貯蔵温度: -20 °C · Sealed in dry,Store in freezer, under -20°C
溶解性: DMSO（少々）、メタノール（少々）
酸解離定数(Pka): 9.86 · 9.86±0.26(Predicted)
外見: 個体
色: ホワイトからオフホワイト
InChIKey: DQXPFAADCTZLNL-PYWTXGKPNA-N

安全と法規制

安全データ

hs_code: 2941.90.3000

化学と産業

応用分野 · 3 件

説明Pneumocandin B0 is an antifungal lipopeptide that acts by inhibiting the synthesis of β-(1,3)-D-glucan, a component of fungal cell walls (IC50s = 70 and 67 ng/ml for inhibiting glucan synthase in C. albicans and A. fumigatus, respectively). It can be used to synthesize the echinocandin caspofungin acetate .

使用Pneumocandin B0 is the major analogue of a family of lipopeptides isolated from several species of several different genera, such as Cryptosporiopsis, Glarea and Pezicula. Pneumocandin B0 is a potent antifungal and acts by inhibition of the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi.

一般的な説明Pneumocandin B0, the precursor of the antifungal drug caspofungin, is a lipohexapeptide produced by the fungus Glarea lozoyensis. Oxidative stress and the resulting reactive oxygen species (ROS) are involved in regulating the biosynthesis of it. Acetyl-CoA and NADPH are major factors limiting the biosynthesis of pneumocandin B0. Other metabolites, such as pyruvate, α-ketoglutaric acid, lactate, unsaturated fatty acids, and metabolite γ-aminobutyric acid, also play an important role in the biosynthesis of pneumocandin B0 and cell growth[1-2].

サプライヤー100 社

北京华美互利生物化工010-56205725 · [email protected]

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

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广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

補足説明 · 1 件

定義ChEBI: An echinocandin initially isolated as a very minor bioactive fermentation product of Glarea lozoyensis (originally known as Zalerion arboricola). Subsequent random mutagenesis work and optimisation of the fermentation medium permi ted the industrial production of pneumocandin B0, which is used as the starting point for the synthesis of the antifungal drug caspofungin.