基本情報
- 標準SMILES
CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)NC(Cc1cnc[nH]1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(N)=O)C(C)C- InChIKey
WHNFPRLDDSXQCL-PDEGJNOBSA-N- 分子式
- C77H109N21O19S
- 平均分子量
- 1,664.9 g/mol
概要
CZEN-002 is a novel, non-azole anti-fungal synthetic octapeptide, derived from alpha-Melanocyte-Stimulating Hormone (a-MSH). CZEN-002 modulates inflammatory and immune responses. It has also been shown to kill Candida albicans (C. albicans), a single-celled fungal organism that causes a variety of infections, including vaginitis. This organism can invade tissues and produce fatal infections in individuals with compromised immune systems such as those suffering from HIV/AIDS or undergoing organ or bone transplants. The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified. Studies attempting to understand the candidacidal activity of derivatives of alpha-MSH have focused on the alpha-MSH amino acid sequence (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors. A second focus was on the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity.
名称と識別子
- 優先名称
- Czen 002
- IUPAC
- (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-[[1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
名称と別名
CZEN 002RefChem:581443(4S)-4-(((2S)-2-(((2S)-2-(((2S)-2-(((2S)-2-acetamido-3-hydroxypropanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-3-hydroxypropanoyl)amino)-4-methylsulfanylbutanoyl)amino)-5-((1-(((2S)-1-(((2S)-1-(((2S)-1-((2-(((2S)-6-amino-1-((2S)-2-(((2S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxohexan-2-yl)amino)-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-5-carbamimidamido-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-[[1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acidSCHEMBL29355455
物性
構造計算による物性
- XLogP
- -4.3
- 極性表面積
- 668 Ų
- 水素結合供与体数
- 23
- 水素結合受容体数
- 23
- 回転可能結合数
- 51
- 重原子数
- 118
- 形式電荷
- 0
- 複雑度
- 3,370
化学と産業
薬理情報
Pharmacodynamics
CZEN-002 is a novel, non-azole anti-fungal synthetic octapeptide, derived from alpha-Melanocyte-Stimulating Hormone (a-MSH). CZEN-002 modulates inflammatory and immune responses. It has also been shown to kill Candida albicans (C. albicans). The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified.
Mechanism of Action
The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified. Studies attempting to understand the candidacidal activity of derivatives of alpha-MSH have focused on the alpha-MSH amino acid sequence (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors. A second focus was on the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity.
関連反応
6 件
化合物ノート
読み込み中…