基本情報
- CAS
522-17-8- 標準SMILES
COc1cc2c(cc1OC)[C@@H]1C(=O)c3ccc4c(c3O[C@@H]1CO2)C=CC(C)(C)O4- InChIKey
ORDAZKGHSNRHTD-UXHICEINSA-N- 分子式
- C23H22O6
- 平均分子量
- 394.4 g/mol
- 単同位体質量
- 394.14163842
概要
Deguelin is a rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. It has a role as an antiviral agent, an antineoplastic agent, a mitochondrial NADH:ubiquinone reductase inhibitor, an angiogenesis inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is an aromatic ether, an organic heteropentacyclic compound, a diether and a member of rotenones.
名称と識別子
- 優先名称
- Deguelin
- IUPAC
- (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
- 現地名
- (7aS)-3,3-ジメチル-9,10-ジメトキシ-7,7aα,13,13aα-テトラヒドロ-3H-ビス[1]ベンゾピラノ[3,4-b:6',5'-e]ピラン-7-オン
- 英語名
- DEGUELIN
- 分子式
- C23H22O6
- 分子量
- 394.42
名称と別名
Deguelin522-17-8(-)-cis-deguelinCHEBI:4357K5Z93K66IEDTXSID10200231(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo(12.8.0.03,12.04,9.015,20)docosa-3(12),4(9),5,10,15,17,19-heptaen-13-oneRefChem:919766DTXCID1012272213,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one(7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one
名称をさらに表示
デグエリン(7aα)-13,13aα-ジヒドロ-9,10-ジメトキシ-3,3-ジメチル-3H-ビス[1]ベンゾピラノ[3,4-b:6',5'-e]ピラン-7(7aH)-オン(7aS)-3,3-ジメチル-9,10-ジメトキシ-7,7aα,13,13aα-テトラヒドロ-3H-ビス[1]ベンゾピラノ[3,4-b:6',5'-e]ピラン-7-オン(7aS,13aS)-13,13a-ジヒドロ-9,10-ジメトキシ-3,3-ジメチル-3H-ビス[1]ベンゾピラノ[3,4-b:6',5'-e]ピラン-7(7aH)-オンデグエリン=(-)-デグエリン3,3-ジメチル-9,10-ジメトキシ-7,7aα,13,13aα-テトラヒドロ-3H-ビス[1]ベンゾピラノ[3,4-b:6',5'-e]ピラン-7-オン
物性
構造計算による物性
- XLogP
- 3.7
- 極性表面積
- 63.2 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 6
- 回転可能結合数
- 2
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 674
実験および物理化学的性質
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Rotenoid flavonoids [PK1206]
SpringerMaterials PropertiesChemical shift
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section194.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 85 · 85-87 °C(lit.)
- 比旋光度
- 27 · D27 -97.2° (c = 0.2 in benzene)
- 沸点
- 560.1 · 560.1±50.0 °C(Predicted)
- 比重(密度)
- 1 · 1+-.0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 10 mg/mL · DMSO: >10 mg/mL
- 外見
- 個体
- 色
- 白から黄色
- 安定性
- -20 °Cで最大3か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大3か月保存できます。
- InChI
- 1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
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。
安全データ
- wgk
- 3
- rtecs
- DX1500000
- hs_code
- 29329990
- safety_code
- 22-24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
応用分野
用途シグナル伝達研究、阻害剤。
説明Rotenoids, deriving from the flavonoid family of compounds, act as chemopreventive agents that inhibit NADH:ubiquinone oxidoreductase activity and suppress phorbol ester-induced ornithine decarboxylase (ODC) activity. The rotenoid compound deguelin, originally isolated from the bark of M. sericea (Leguminosae) to be used as an insecticide and fish poison, has chemopreventive and chemosensitizing effects in models of skin, mammary, colon, and lung carcinogenesis. Deguelin inhibits cell growth (IC50 = 8 M), blocks PI3K/Akt activation, suppresses COX-2 expression, and induces apoptosis in premalignant and squamous human bronchial epithelial (HBE) cells without affecting normal HBE cells. At 6 mg/kg, deguelin induces Parkinson’s disease-like symptoms in rats after six days of subcutaneous infusion and therefore may also serve as a useful model for Parkinson’s disease research.
使用Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers.
上流・下流製品情報
上流原料
サプライヤー100 社
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