DEGUELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H22O6
Molecular Weight	394.4172
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C2[C@H]3[C@@H](COC2=C1)OC4=C5C=CC(C)(C)OC5=CC=C4C3=O

InChI

InChIKey=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

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Potency
PI3-kinase class I 8 Target ID: CHEMBL3559703 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15916691	Inhibitor 8504
Nuclear factor NF-kappa-B complex 11 Target ID: CHEMBL2094258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18841906	Inhibitor 8504	0.19 µM [IC50]
Ornithine decarboxylase 15 Target ID: CHEMBL1869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9834970	Inhibitor 8504	13.0 nM [IC50]

PubMed

Title	Date	PubMed
Deguelin, a selective silencer of the NPM1 mutant, potentiates apoptosis and induces differentiation in AML cells carrying the NPM1 mutation.	2015-02	25242579
Deguelin, an Akt inhibitor, down-regulates NF-κB signaling and induces apoptosis in colon cancer cells and inhibits tumor growth in mice.	2012-11	22623043
Induction of DNA damage by deguelin is mediated through reducing DNA repair genes in human non-small cell lung cancer NCI-H460 cells.	2012-04	22227970
Deguelin attenuates reperfusion injury and improves outcome after orthotopic lung transplantation in the rat.	2012	22745725
Anticancer efficacy of deguelin in human prostate cancer cells targeting glycogen synthase kinase-3 β/β-catenin pathway.	2011-12-15	21472727
Deguelin--an inhibitor to tumor lymphangiogenesis and lymphatic metastasis by downregulation of vascular endothelial cell growth factor-D in lung tumor model.	2010-11-15	20162567
Deguelin promotes apoptosis and inhibits angiogenesis of gastric cancer.	2010-10	20811676
Suppression of lung tumorigenesis by leucine zipper/EF hand-containing transmembrane-1.	2010-09-02	20824095
Inhibition of Cell Proliferation and MAP Kinase and Akt Pathways in Oral Squamous cell Carcinoma by Genistein and Biochanin A.	2010-09	18955325
Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.	2010-08-23	20572190
Natural toxins for use in pest management.	2010-08	22069667
[Separation and preparation of two rotenoids from the roots of Derris by high-speed counter-current chromatography].	2010-08	21261054
A comprehensive panel of three-dimensional models for studies of prostate cancer growth, invasion and drug responses.	2010-05-03	20454659
Differential chemosensitization of P-glycoprotein overexpressing K562/Adr cells by withaferin A and Siamois polyphenols.	2010-05-03	20438634
Deguelin suppresses cell proliferation via the inhibition of survivin expression and STAT3 phosphorylation in HTLV-1-transformed T cells.	2010-03	19781773
Cardiotoxicity of anticancer drugs: the need for cardio-oncology and cardio-oncological prevention.	2010-01-06	20007921
A novel inhibitor of the PI3K/Akt pathway based on the structure of inositol 1,3,4,5,6-pentakisphosphate.	2010-01-05	20051961
The role of the Akt/mTOR pathway in tobacco carcinogen-induced lung tumorigenesis.	2010-01-01	20028747
IGF1 activates cell cycle arrest following irradiation by reducing binding of ΔNp63 to the p21 promoter.	2010	21480565
Parkinson's disease: is it a toxic syndrome?	2010	21152209
1-Nitropyrene stabilizes the mRNA of cytochrome P450 1a1, a carcinogen-metabolizing enzyme, via the Akt pathway.	2009-12	19961161
Acute inhibition of selected membrane-proximal mouse T cell receptor signaling by mitochondrial antagonists.	2009-11-10	19901985
A novel look into estrogen receptor-negative breast cancer prevention with the natural, multifunctional signal transduction inhibitor deguelin.	2009-11	19861544
Deguelin inhibits growth of breast cancer cells by modulating the expression of key members of the Wnt signaling pathway.	2009-11	19861542
Optimising resolution for a preparative separation of Chinese herbal medicine using a surrogate model sample system.	2009-06-26	19447397
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009-06-25	19557182
Deguelin blocks cells survival signal pathways and induces apoptosis of HL-60 cells in vitro.	2009-06	19455392
Involvement of SRC-3 in deguelin-induced apoptosis in Jurkat cells.	2009-06	19365708
Nitric oxide inhibitory principles from Derris trifoliata stems.	2009-06	19303755
Liposomal encapsulation of deguelin: evidence for enhanced antitumor activity in tobacco carcinogen-induced and oncogenic K-ras-induced lung tumorigenesis.	2009-04	19336726
Synergistic effect of ERK inhibition on tetrandrine-induced apoptosis in A549 human lung carcinoma cells.	2009-03	19255520
Targeting heat shock protein 90 overrides the resistance of lung cancer cells by blocking radiation-induced stabilization of hypoxia-inducible factor-1alpha.	2009-02-15	19176399
Simultaneous blockade of AP-1 and phosphatidylinositol 3-kinase pathway in non-small cell lung cancer cells.	2008-12-16	19018257
Angiogenesis in pre-malignant conditions.	2008-12-16	18941463
A novel derivative of the natural agent deguelin for cancer chemoprevention and therapy.	2008-12	19139008
Deguelin inhibits retinal neovascularization by down-regulation of HIF-1alpha in oxygen-induced retinopathy.	2008-12	18208562
Phenolic constituents of Amorpha fruticosa that inhibit NF-kappaB activation and related gene expression.	2008-10	18841906
Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.	2008-10	18817445
Deguelin inhibits human hepatocellular carcinoma by antiangiogenesis and apoptosis.	2008-07	18575727
Enhancement radiosensitization of breast cancer cells by deguelin.	2008-06	18593368
Antiangiogenic effect of deguelin on choroidal neovascularization.	2008-02	17967937
Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography.	2008-01-18	18082754
Deguelin represses both the expression of nucleophosmin and some nucleoporins: Nup88 and Nup214 in Jurkat cells.	2008-01	18175937
Studies on cellular resilience and adaptation following acute and repetitive exposure to ozone in cultured human epithelial (HeLa) cells.	2008	18339251
Implication of AMP-activated protein kinase and Akt-regulated survivin in lung cancer chemopreventive activities of deguelin.	2007-12-15	18089792
The phosphoinositide 3-kinase pathway in human cancer: genetic alterations and therapeutic implications.	2007-08	19384426
Mechanism of uptake and retention of F-18 BMS-747158-02 in cardiomyocytes: a novel PET myocardial imaging agent.	2007-06-04	18022104
NADH: ubiquinone oxidoreductase inhibitors block induction of ornithine decarboxylase activity in MCF-7 human breast cancer cells.	1998-11	9834970
Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent.	1997-08-15	9270009
Anomalous structure-activity relationships of 13-homo-13-oxarotenoids and 13-homo-13-oxadehyrorotenoids.	1997-08	9282833

Name

Type

Language

(7AS,13AS)-13,13A-DIHYDRO-9,10-DIMETHOXY-3,3-DIMETHYL-3H-(1)BENZOPYRANO(3,4-B)PYRANO(2,3-H)(1)BENZOPYRAN-7(7AH)-ONE

Preferred Name

English

DEGUELIN

Common Name

English

DEGUELIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1745