基本情報
- CAS
21884-44-6- 標準SMILES
Cc1cc(O)c2c(c1O)C(=O)C13C(=C2O)C(=O)C2C(O)C1C1C(O)C3C(=O)C3=C(O)c4c(O)cc(C)c(O)c4C(=O)C321- InChIKey
FAZDYVMEXQHRLI-UHFFFAOYSA-N- 分子式
- C30H22O12
- 平均分子量
- 574.5 g/mol
- 単同位体質量
- 574.11112613
概要
Luteoskyrin is a cyclic ketone and an organic polycyclic compound.
名称と識別子
- 優先名称
- Luteoskyrin
- IUPAC
- 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone
- 現地名
- (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-8,8'-ジヒドロキシルグロシン
- 英語名
- Rugulosin, 8,8'-dihydroxy-, (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-
- 分子式
- C30H22O12
- 分子量
- 574.49
名称と別名
LUTEOSKYRIN(-)-Luteoskyrin8,8'-Dihydroxyrugulosin21884-44-6NSC160879Flavomycelin5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetroneRUGULOSIN, 8,8'-DEHYDROXY-Luteoskyrin, (-)-NSC-1608792,2',4,4'5,5',8,8'-Octahydroxy-2,2',3,3'-tetrahydro-7,7'-dimethyl-1,1'-bianthraquinone5H,6H-6,13a,5a,14-(1,2,3,4)Butanetetraylcycloocta(1,2-b:5,6-b')dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-
名称をさらに表示
ルテオスキリン(-)-ルテオスキリン(1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-8,8'-ジヒドロキシルグロシン[1S,1'S,2R,2'R,3S,3'S,9aR,9'aR,(-)]-8,8'-ジヒドロキシルグロシン(-)-ルテオスカイリンルテオスカイリン(1S,2R,13S,14R,15S,16S,17R,28R)-5,8,12,14,20,23,27,28-オクタヒドロキシ-6,21-ジメチルオクタシクロ[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]オクタコサ-4,6,8,11,19,21,23,26-オクタエン-3,10,18,25-テトラオン
物性
構造計算による物性
- XLogP
- 1.3
- 極性表面積
- 230 Ų
- 水素結合供与体数
- 8
- 水素結合受容体数
- 12
- 回転可能結合数
- 0
- 重原子数
- 42
- 形式電荷
- 0
- 複雑度
- 1,360
物理化学的性質
- 融点
- 278 °C · 278°C (rough estimate)
- 沸点
- 555.89 °C · 555.89°C (rough estimate)
- 比重(密度)
- 1.3474 · 1.3474 (rough estimate)
- 屈折率
- 1.648 · 1.6480 (estimate)
- 酸解離定数(Pka)
- 4.2 · 4.20±1.00(Predicted)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
Health EffectsLuteoskyrin is hepatotoxic and hepatocarcinogenic, causing hepatic disorders such as liver
cirrhosis and liver tumors. (A3069, A3070)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Luteoskyrin is hepatotoxic. It is thought that this is a result of its metabolic reduction to the semiquinone radical catalyzed by NADPH-dependent cytochrome reductases in the liver, leading to the generation of active oxygen species in redox systems. This causes the induction of lipid peroxidation, hepatocellular membrane damage, and elevation of serum transaminase activities, resultin in liver injuries. Luteoskyrin is also hepatocarcinogenic, possibly a result of its ability to induce DNA fragmentation. It is able to bind to DNA, forming chelate-complexes with nucleic acids and select metal ions. Luteoskyrin inhibits the replication, transcription and repair of DNA, which is at least partially because it inhibits RNA polymerase and ribonuclease H. (A2955, A3042, A3070, A3071, A3072)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
安全データ
- 有毒物質データの
- 21884-44-6(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/MetabolitesLuteoskyrin accumulates selectively in the liver, with minor distribution to the serum and kidneys. In the liver it is reduced to its semiquinone radical by NADPH-dependent cytochrome reductases. (A3070,A3071)
用途と製造
UsesLuteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice. (A3069)
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