カスポファンギン

n-{(2r,6s,9s,11r,12s,14As,15s,20s,23s,25as)-12-[(2-aminoethyl)amino]-20-[(1r)-3-amino-1-hydroxypropyl]-23-[(1s,2s)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1r)-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-dimethyltetradecanamide

HCID 2826718

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 162808-62-0
標準SMILES: CCC(C)CC(C)CCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](NCCN)NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@H]([C@H](O)CCN)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: JYIKNQVWKBUSNH-OGZDCFRISA-N
分子式: C52H88N10O15
平均分子量: 1,093.3 g/mol
単同位体質量: 1,092.64306212

名称と識別子

優先名称: n-{(2r,6s,9s,11r,12s,14As,15s,20s,23s,25as)-12-[(2-aminoethyl)amino]-20-[(1r)-3-amino-1-hydroxypropyl]-23-[(1s,2s)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1r)-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-dimethyltetradecanamide
IUPAC: N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-aminoethylamino)-3-[(1R)-3-amino-1-hydroxypropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-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: カスポファンギン
英語名: Caspofungin
分子式: C52H88N10O15
分子量: 1093.31

名称と別名

MK-991Caspofungin (INN)N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-aminoethylamino)-3-[(1R)-3-amino-1-hydroxypropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-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-dimethyltetradecanamideCaspofungin (Base)CHEMBL499808SCHEMBL6726364JYIKNQVWKBUSNH-OGZDCFRISA-NN-[(2-aminoethylamino)-[(1R)-3-amino-1-hydroxy-propyl]-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-trihydroxy-[(1R)-1-hydroxyethyl]-hexaoxo-[?]yl]-10,12-dimethyl-tetradecanamideBDBM50478215NSC754342NSC-754342n-{(2r,6s,9s,11r,12s,14as,15s,20s,23s,25as)-12-[(2-aminoethyl)amino]-20-[(1r)-3-amino-1-hydroxypropyl]-23-[(1s,2s)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1r)-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-dimethyltetradecanamide

名称をさらに表示

カスポファンギンカスポファンジンシクロ[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-Orn-]-3β-ヒドロキシ-L-Pro-[(4R,5S)-N2-[(10R,12S)-10,12-ジメチルテトラデカノイル]-4-ヒドロキシ-5-(2-アミノエチルアミノ)-L-Orn*-]]カスポフンギンシクロ[L-Thr-L-t4Hyp-[(3S,4S)-3,4-ジヒドロキシ-4-(4-ヒドロキシフェニル)-L-Abu-]-[(3R)-3-ヒドロキシ-L-Orn-]-[(3S)-3-ヒドロキシ-L-Pro-]-[(4R,5S)-5-[(2-アミノエチル)アミノ]-4-ヒドロキシ-N2-[(10R,12S)-10,12-ジメチル-1-オキソテトラデシル]-L-Orn*-]](10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-3-[(1R)-3-アミノ-1-ヒドロキシプロピル]-21-[(2-アミノエチル)アミノ]-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]-11,20,25-トリヒドロキシ-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キャスポファンギンCaspofungineCancidas (tm)m991CS-1171Aids058650CASPOFUNGINAids-058650CASPORFUNGINCaspofungin MK-0991

D07626Q420875N-((2R,6S,9S,11R,12S,14aS,15S,20S,23S,25aS)-20-((R)-3-amino-1-hydroxypropyl)-12-((2-aminoethyl)amino)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,15-trihydroxy-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-dimethyltetradecanamidePneumocandin B0, 1-[(4R,5S)-5-[(2-aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-(threo-3-hydroxy-L-ornithine)-Pneumocandin B0, 1-[(4R,5S)-5-[(2-aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]- (9CI)

データベース識別子

CAS: 162808-62-0
PubChem CID: 2826718
DTXSID: DTXSID30873204
ChEMBL: CHEMBL499808

物性

構造計算による物性

XLogP: 0.3
極性表面積: 412 Å²
水素結合供与体数: 16
水素結合受容体数: 18
回転可能結合数: 23
重原子数: 77
形式電荷: 0
複雑度: 1,900

物理化学的性質

沸点: 1408.1 · 1408.1±65.0 °C(Predicted)
比重(密度): 1.36 · 1.36±0.1 g/cm3(Predicted)
酸解離定数(Pka): 9.86 · 9.86±0.26(Predicted)
InChIKey: YYVNXPANLUFPHU-QDFTWGMZNA-N

安全と法規制

安全データ

有毒物質データの: 162808-62-0(Hazardous Substances Data)

化学と産業

応用分野 · 2 件

用途チャンデイン系抗真菌薬

使用Caspofungin is an antifungal drug, and belongs to a new class termed the echinocandins. It is used to treat Aspergillus and Candida infection, and works by inhibiting cell wall synthesis. Antifungals in the echinocandin class inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-beta glucan synthase. There is a potential for resistance development to occur, however in vitro resistance development to Caspofungin by Aspergillus species has not been studied.

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補足説明

定義ChEBI: A semisynthetic cyclic hexapeptide echinocandin antibiotic which exerts its effect by inhibiting the synthesis of 1,3-beta-D-glucan, an integral component of the fungal cell wall.