CAS 83-79-4|(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,1<sup...

General Information

Structure

Molecular Formula

C₂₃H₂₂O₆

Molecular Mass

394.41718

Exact Mass

394.14163842

Charge

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

Canonic Smiles

COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(=C)C

Isomeric Smiles

c12c(C(=O)[C@H]3c4c(OC[C@H]3O2)cc(c(c4)OC)OC)ccc2c1C[C@@H](O2)C(=C)C

Calculated Properties

JChem

Acid pKa

11.803546

H Acceptors

H Donor

LogD (pH = 5.5)

3.3201776

LogD (pH = 7.4)

3.3201606

Log P

3.3201778

Molar Refractivity

105.7123

Polarizability

41.12286

Polar Surface Area

63.22

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

(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),9,14,16,18-hexaen-12-one (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

IUPAC Traditional name

cube root (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),9,14,16,18-hexaen-12-one

Synonyms

(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)-oneParaderilRotenoneDri-kilDactinolNicoulineTubotoxinTubatoxinRotenoneNoxfishDerrisDerrin鱼滕精

Names and Identifiers

Registration numbers

MeSH Name

Rotenone

Unique Ingredient Identifier

Wikipedia Title

PubChem CID

KEGG ID

CAS Number

CHEBI ID

CHEMBL

Beilstein Number

MDL Number

EC Number

PubChem SID

248993152486920024278683162103190

Registration numbers

Properties

Physical Property

Apperance

Colorless to red

Boiling Point

210-220 °C at 0.5 mmHg

210-220 °C/0.5 mmHg(lit.)

Density

1.27 g/cm³ @ 20 °C

Melting Point

165-166 °C

159-164 °C(lit.)

Solubility

Soluble in ether and acetone, slightly soluble in ethanol

Optical Rotation

[α]20/D -115°, c = 1.4 in chloroform

Pharmacology Properties

Mechanism of Action

Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Rotenone

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.

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.

45656

PS99

Molecule Details

References

PubChem Literature

From Data Sources

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 99A, (ir)

• Abidi, S.L., J. Het. Chem., 1987, 24, 845, (hplc, resoln)

• Blasko, G. et al., J. Nat. Prod., 1989, 52, 1363, (cmr)

• Crombie, L. et al., Phytochemistry, 1998, 49, 1479-1507, (rev, biosynth)

• Reed, R.I. et al., J.C.S., 1963, 5949, (ms)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1424, (occur)

• Unai, T. et al., Agric. Biol. Chem., 1973, 37, 387; 897, (synth)

• Sasaki, I. et al., Agric. Biol. Chem., 1979, 43, 137, (synth)

• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A363

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1131

• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)

• Bhandari, P. et al., J.C.S. Perkin 1, 1992, 839; 851, (biosynth)

• Handbook of Pesticide Toxicology, (Eds. Hayes, W.J. et al), Academic Press, 1991, 599, (tox, rev)

• Carlson, D.G. et al., Tetrahedron, 1973, 29, 2731, (pmr)

• Dangerous Prop. Ind. Mater. Rep., 1989, 9, 74, (rev, tox)

• Hayashi, H. et al., Biosci., Biotechnol., Biochem., 1997, 61, 914-916, (activity)

• Pesticide Manual, 9th edn., 1991, No. 10610

• Bchi, G. et al., J.C.S., 1961, 2843, (abs config)

• Crombie, L. et al., J.C.S. Perkin 1, 1973, 1277; 1285; 1975, 1497, (synth, biosynth, cmr)

• Begley, M.J. et al., Chem. Comm., 1975, 850, (cryst struct)

• Nunlist, R. et al., J. Het. Chem., 1988, 25, 351, (pmr, cmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RNZ000

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 923A, (nmr)

• Haley, T.J., J. Environ. Pathol. Toxicol., 1978, 1, 315, (rev)

• Rossi, M. et al., Bioorg. Chem., 1988, 16, 376, (cryst struct, conformn)

References

Bioactivity

PubChem BioAssay

Bioactivity