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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
Structure of DIHYDROROTENONE

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

HIDE SMILES / InChI

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

Description
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

Sources: Yakugaku Zasshi (1924), No. 514, 1049-60.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
120.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Quantitative study of mitochondrial complex I in platelets of parkinsonian patients.
1998 Jan
Natural pesticide dihydrorotenone arrests human plasma cancer cells at the G0/G1 phase of the cell cycle.
2014 May
Patents

Patents

Sample Use Guides

LD50 (rat) > 2.5 g/kg
Route of Administration: Oral
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 Sat Dec 16 08:34:27 GMT 2023
Edited
by admin
on Sat Dec 16 08:34:27 GMT 2023
Record UNII
538CX0LPPO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROROTENONE
Common Name English
NSC-53866
Code English
1',2'-DIHYDROROTENONE
Common Name English
NSC-351138
Code English
(1)BENZOPYRANO(3,4-B)FURO(2,3-H)(1)BENZOPYRAN-6(6AH)-ONE, 1,2,12,12A-TETRAHYDRO-8,9-DIMETHOXY-2-(1-METHYLETHYL)-, (2R,6AS,12AS)-
Common Name English
Code System Code Type Description
NSC
53866
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
PRIMARY
CAS
6659-45-6
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
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FDA UNII
538CX0LPPO
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
PRIMARY
PUBCHEM
243725
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
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NSC
351138
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID5041227
Created by admin on Sat Dec 16 08:34:27 GMT 2023 , Edited by admin on Sat Dec 16 08:34:27 GMT 2023
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