(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-one

• ChemBase编号: 119518
• 分子式: C23H22O6
• 平均质量: 394.41718
• 单一同位素质量: 394.14163842
• SMILES: c12c(C(=O)[C@H]3c4c(OC[C@H]3O2)cc(c(c4)OC)OC)ccc2c1C[C@@H](O2)C(=C)C
• Canonical SMILES: COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(=C)C
• InChI: InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
• InChIKey: JUVIOZPCNVVQFO-HBGVWJBISA-N

名称和登记号

名称

• IUPAC标准名: (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^3,^1^1.0^4,^8.0^1^4,^1^9]henicosa-3(11),4(8),9,14(19),15,17-hexaen-12-one; (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^3,^1^1.0^4,^8.0^1^4,^1^9]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• IUPAC传统名: (1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^3,^1^1.0^4,^8.0^1^4,^1^9]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one; cube root
• 别名: 鱼滕精; Tubatoxin; Paraderil; Rotenone; Rotenone; Dactinol; Derrin; Derris; Dri-kil; Nicouline; Noxfish; Tubotoxin; (2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

登记号

• CAS号: 83-79-4
• EC号: 201-501-9
• MDL号: MFCD09025614
• Beilstein号: 6773081
• PubChem SID: 24899315; 162103190; 24278683; 24869200
• PubChem CID: 6758
• CHEBI ID: 28201
• CHEMBL: 429023
• KEGG ID: C07593
• 医学主题词(MeSH): Rotenone
• 美国药典/FDA物质标识码: 03L9OT429T
• 维基百科标题: Rotenone

理论计算性质

• Acid pKa: 11.803546
• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): 3.3201776
• LogD (pH = 7.4): 3.3201606
• Log P: 3.3201778
• 摩尔折射率: 105.7123 cm^3
• 极化性: 41.12286 Å^3
• 极化表面积: 63.22 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Soluble in ether and acetone, slightly soluble in ethanol
• 外观: Colorless to red
• 熔点: 159-164 °C(lit.); 165-166 °C
• 沸点: 210-220 °C/0.5 mmHg(lit.); 210-220 °C at 0.5 mmHg
• 密度: 1.27 g/cm^3 @ 20 °C
• 比旋光度: [α]20/D -115°, c = 1.4 in chloroform

安全信息

• RTECS编号: DJ2800000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25-36/37/38-50/53
• 安全公开号: 22-24/25-36-45-60-61
• GHS危险品标识: GHS06; GHS09
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335-H410
• GHS警示性声明: P261-P273-P301 + P310-P305 + P351 + P338-P501
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 生物活性机理: Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone

产品相关信息

• 纯度: ≥95%; 95%; 95+%
• 级别: analytical standard; PESTANAL®, analytical standard
• 包装: ampule of 250 mg
• 杂质: <5% dimethyl phthalate (extraction solvent)
• 生物来源: Constit. of the root of Derris elliptica . Widely distrib. in the Leguminosae (Papilionoideae) e.g. in many other Derris spp. Lonchocarpus spp. Millettia spp., Tephrosia spp., Amorpha fruticosa, Antheroporum pierrei, Crotalaria burhia, Crotalaria medicaginea, Mundulea pauciflora, Mundulea sericea, Neorautanenia amboensis, Neorautanenia ficifolia, Ormocarpum glabrum, Pachyrrhizus erosus, Piscidia erythrina, Piscidia mollis, Poiretia tetraphylla and Spatholobus roxburghii. Also in Verbascum thapsus (Scrophulariaceae)
• 应用领域: Antineoplastic agent; Contact insecticide and pesticide; Potent mitochondrial poison
• Empirical Formula (Hill Notation): C23H22O6

详细说明

Sigma Aldrich - R8875

包装
1, 5, 10, 25 g in glass bottle
Biochem/physiol Actions
Inhibitor of mitochondrial electron transport at NADH:ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone is used to induce a Parkinson-like syndrome as an experimental model in rats.
Inhibitor of mitochondrial electron transport. Neurotoxic agent that can produce a Parkinson-like condition as an animal model for study of etiology and interventions.

Sigma Aldrich - 477737

Biochem/physiol Actions
Inhibitor of mitochondrial electron transport at NADH:ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone is used to induce a Parkinson-like syndrome as an experimental model in rats.
Inhibitor of mitochondrial electron transport. Neurotoxic agent that can produce a Parkinson-like condition as an animal model for study of etiology and interventions.

Sigma Aldrich - PS99

Biochem/physiol Actions
Inhibitor of mitochondrial electron transport at NADH:ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone is used to induce a Parkinson-like syndrome as an experimental model in rats.
Inhibitor of mitochondrial electron transport. Neurotoxic agent that can produce a Parkinson-like condition as an animal model for study of etiology and interventions.

Sigma Aldrich - 45656

Biochem/physiol Actions
Inhibitor of mitochondrial electron transport at NADH:ubiquinone oxidoreductase. It is readily absorbed through the exoskeletons of arthropods, but poorly absorbed cutaneously or from the gastrointestinal tract of mammals. Rotenone is used to induce a Parkinson-like syndrome as an experimental model in rats.
Inhibitor of mitochondrial electron transport. Neurotoxic agent that can produce a Parkinson-like condition as an animal model for study of etiology and interventions.
法律信息
PESTANAL 注册商标 Sigma-Aldrich Laborchemikalien GmbH

参考文献

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