(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 ID: 119518
• Molecular Formular: C23H22O6
• Molecular Mass: 394.41718
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Synonyms: 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; 鱼滕精

Database IDs

• CAS Number: 83-79-4
• EC Number: 201-501-9
• MDL Number: MFCD09025614
• Beilstein Number: 6773081
• PubChem SID: 24899315; 162103190; 24278683; 24869200
• PubChem CID: 6758
• CHEBI ID: 28201
• CHEMBL: 429023
• KEGG ID: C07593
• MeSH Name: Rotenone
• Unique Ingredient Identifier: 03L9OT429T
• Wikipedia Title: Rotenone

CALCULATED PROPERTIES

• Acid pKa: 11.803546
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.3201776
• LogD (pH = 7.4): 3.3201606
• Log P: 3.3201778
• Molar Refractivity: 105.7123 cm^3
• Polarizability: 41.12286 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in ether and acetone, slightly soluble in ethanol
• Apperance: Colorless to red
• Melting Point: 159-164 °C(lit.); 165-166 °C
• Boiling Point: 210-220 °C/0.5 mmHg(lit.); 210-220 °C at 0.5 mmHg
• Density: 1.27 g/cm^3 @ 20 °C
• Optical Rotation: [α]20/D -115°, c = 1.4 in chloroform

Safety Information

• RTECS: DJ2800000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38-50/53
• Safety Statements: 22-24/25-36-45-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335-H410
• GHS Precautionary statements: P261-P273-P301 + P310-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Mechanism of Action: Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone

Product Information

• Purity: ≥95%; 95%; 95+%
• Grade: analytical standard; PESTANAL®, analytical standard
• Packaging: ampule of 250 mg
• Impurities: <5% dimethyl phthalate (extraction solvent)
• Biological Source: 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)
• Application(s): Antineoplastic agent; Contact insecticide and pesticide; Potent mitochondrial poison
• Empirical Formula (Hill Notation): C23H22O6

DETAILS

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.
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

REFERENCES

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