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Merck
CN

D0817

(−)-Deguelin

>98% (HPLC), activated Akt inhibitor, powder

Synonym(s):

(7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one

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About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
522-17-8
Molecular Weight:
394.42
UNSPSC Code:
12352200
PubChem Substance ID:
329798641
NACRES:
NA.77
MDL number:
MFCD01740600

Key Documents

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Product Name

(−)-Deguelin, >98% (HPLC), powder

SMILES string

COc1cc2OC[C@H]3Oc4c(ccc5OC(C)(C)C=Cc45)C(=O)[C@H]3c2cc1OC

InChI key

ORDAZKGHSNRHTD-UXHICEINSA-N

InChI

1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

assay

>98% (HPLC)

form

powder

optical activity

[α]/D -70 to -80°, c = 0.2 in methanol

color

white to beige

mp

85-87 °C (lit.)

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

Quality Level

100

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Application

(−)-Deguelin has been used as:
  • a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
  • an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
  • an analytical standard in high-performance liquid chromatography (HPLC)

Biochem/physiol Actions

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.
Inhibitor of activated Akt. Does not affect MAPK, ERK1/2, or JNK. Anticancer, chemoprotective agent.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000367197
0000363676
0000363676
0000367197
0000146801

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Wanda van der Stel et al.
Archives of toxicology, 94(8), 2731-2732 (2020-07-29)
In the original publication of the article.
José Garcia et al.
Bioorganic & medicinal chemistry, 20(2), 672-680 (2011-11-01)
Deguelin, a rotenoid, has emerged as an attractive pharmacophore for chemoprevention showing in vivo activity in several xenografts. Recently, several lines of evidence have suggested its mode of action may involve inhibition of HSP90, however binding in a different mode
Sebastian J Buss et al.
American journal of physiology. Heart and circulatory physiology, 302(2), H420-H430 (2011-11-08)
The attenuation of adverse myocardial remodeling and pathological left ventricular (LV) hypertrophy is one of the hallmarks for improving the prognosis after myocardial infarction (MI). The protein kinase Akt plays a central role in regulating cardiac hypertrophy, but the in
Rahel Sarah Varughese et al.
Cancer, 125(11), 1789-1798 (2019-04-02)
Deguelin is a rotenoid compound that exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants. An analysis of evidence from both in vitro and in vivo studies suggests that deguelin displays potent anticancer
Zhao-hui Chu et al.
Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine, 9(5), 533-538 (2011-05-14)
To study the effects of deguelin on proliferation and apoptosis of human breast cancer cell line MCF-7 and on phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt) signaling pathway. After treatment with 0, 1, 5, 10, 15 and 20 μmol/L of deguelin for
View All Related Papers

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