Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H24O6 |
Molecular Weight | 396.4331 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C4=C(O2)C5=C(O[C@H](C5)C(C)C)C=C4
InChI
InChIKey=DTFARBHXORYQBF-HBGVWJBISA-N
InChI=1S/C23H24O6/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/h5-7,9,11,16,20-21H,8,10H2,1-4H3/t16-,20-,21+/m1/s1
Molecular Formula | C23H24O6 |
Molecular Weight | 396.4331 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/23922854Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24615755 | https://www.ncbi.nlm.nih.gov/pubmed/13069324 | https://www.ncbi.nlm.nih.gov/pubmed/17241123
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23922854
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24615755 | https://www.ncbi.nlm.nih.gov/pubmed/13069324 | https://www.ncbi.nlm.nih.gov/pubmed/17241123
Dihydrorotenone (DHR) is a potent mitochondrial inhibitor and natural pesticide widely used in farming industry. Mechanistic investigations suggested that Dihydrorotenone bound to and inhibited the complex I in the electron transport chain, thus inhibiting mitochondrial function and decreasing ATP production. Inhibition of mitochondrial function and disruption of the energy supply lead to insect death. Although Dihydrorotenone is non-toxic in rats, it induces Parkinsonian syndrome in the long-term treated mice, which suggesting Dihydrorotenone is toxic to neural cells.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17241123 |
120.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13069324
LD50 (rat) > 2.5 g/kg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24615755
Human plasma cell lines (LP1, KMS11, OPM2, H929) were used for activity evaluation. Plasma cells were cultured in 96-well plates at a
density of 1.5 Ч 104 cells per well and treated with 0, 0.39, 0.78, 1.56, 3.12, 6.25, 12.5, and 25 μM of DHR (Dihydrorotenone). After 72-h incubation, tetrazolium (MTT) was added to each well to a final concentration of 5.0 mg/mL and incubated for 4 h. Formazan crystals resulting from MTT reduction were dissolved in 100 μL of sodium dodecyl sulfate (SDS) buffer (containing 10% SDS and 0.01 M HCl). The absorbance was detected at 570 and 650 nm using a plate reader (SpectraMax M5; Molecular Devices, Sunnyvale, CA). Relative viable cells were calculated from the difference of OD570 and OD650.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:34:27 GMT 2023
by
admin
on
Sat Dec 16 08:34:27 GMT 2023
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Record UNII |
538CX0LPPO
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Record Status |
Validated (UNII)
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Record Version |
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