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

[H][C@@]12COC3=CC(OC)=C(OC)C=C3[C@]1([H])C(=O)C4=CC=C5OC(C)(C)C=CC5=C4O2

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

Molecular Formula	C23H22O6
Molecular Weight	394.4172
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8297
Nuclear factor NF-kappa-B complex 11 Target ID: CHEMBL2094258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18841906	Inhibitor 8297	0.19 µM [IC50]
Ornithine decarboxylase 15 Target ID: CHEMBL1869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9834970	Inhibitor 8297	13.0 nM [IC50]

PubMed

Title	Date	PubMed
		252159983
Anomalous structure-activity relationships of 13-homo-13-oxarotenoids and 13-homo-13-oxadehyrorotenoids.	1997 Aug	9282833
Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent.	1997 Aug 15	9270009
NADH: ubiquinone oxidoreductase inhibitors block induction of ornithine decarboxylase activity in MCF-7 human breast cancer cells.	1998 Nov	9834970
Deguelin inhibits expression of IkappaBalpha protein and induces apoptosis of B-CLL cells in vitro.	2007 Aug	17568818
Implication of AMP-activated protein kinase and Akt-regulated survivin in lung cancer chemopreventive activities of deguelin.	2007 Dec 15	18089792
[Deguelin regulates cell cycle and nuclear pore complex protein Nup98 and Nup88 in U937 cells in vitro].	2007 Feb	17650673
[Effect of deguelin on proliferation and apoptosis of lymphoma Daudi cells and its mechanism].	2007 Mar	17649631
Direct evidence for the action of phosphatidylinositol (3,4,5)-trisphosphate-mediated signal transduction in the 2-cell mouse embryo.	2007 Nov	17634444
Mechanism of uptake and retention of F-18 BMS-747158-02 in cardiomyocytes: a novel PET myocardial imaging agent.	2007 Nov-Dec	18022104
Studies on cellular resilience and adaptation following acute and repetitive exposure to ozone in cultured human epithelial (HeLa) cells.	2008	18339251
A novel derivative of the natural agent deguelin for cancer chemoprevention and therapy.	2008 Dec	19139008
Deguelin inhibits retinal neovascularization by down-regulation of HIF-1alpha in oxygen-induced retinopathy.	2008 Dec	18208562
Simultaneous blockade of AP-1 and phosphatidylinositol 3-kinase pathway in non-small cell lung cancer cells.	2008 Dec 16	19018257
Angiogenesis in pre-malignant conditions.	2008 Dec 16	18941463
Antiangiogenic effect of deguelin on choroidal neovascularization.	2008 Feb	17967937
Deguelin represses both the expression of nucleophosmin and some nucleoporins: Nup88 and Nup214 in Jurkat cells.	2008 Jan	18175937
Identification of novel antiangiogenic anticancer activities of deguelin targeting hypoxia-inducible factor-1 alpha.	2008 Jan 1	17764071
Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography.	2008 Jan 18	18082754
Deguelin inhibits human hepatocellular carcinoma by antiangiogenesis and apoptosis.	2008 Jul	18575727
Enhancement radiosensitization of breast cancer cells by deguelin.	2008 Jun	18593368
Phenolic constituents of Amorpha fruticosa that inhibit NF-kappaB activation and related gene expression.	2008 Oct	18841906
Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.	2008 Oct	18817445
Liposomal encapsulation of deguelin: evidence for enhanced antitumor activity in tobacco carcinogen-induced and oncogenic K-ras-induced lung tumorigenesis.	2009 Apr	19336726
1-Nitropyrene stabilizes the mRNA of cytochrome P450 1a1, a carcinogen-metabolizing enzyme, via the Akt pathway.	2009 Dec	19961161
Involvement of SRC-3 in deguelin-induced apoptosis in Jurkat cells.	2009 Jun	19365708
Nitric oxide inhibitory principles from Derris trifoliata stems.	2009 Jun	19303755
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.	2009 Jun 25	19557182
A novel look into estrogen receptor-negative breast cancer prevention with the natural, multifunctional signal transduction inhibitor deguelin.	2009 Nov	19861544
Acute inhibition of selected membrane-proximal mouse T cell receptor signaling by mitochondrial antagonists.	2009 Nov 10	19901985
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
Natural toxins for use in pest management.	2010 Aug	22069667
[Separation and preparation of two rotenoids from the roots of Derris by high-speed counter-current chromatography].	2010 Aug	21261054
Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.	2010 Aug 23	20572190
The role of the Akt/mTOR pathway in tobacco carcinogen-induced lung tumorigenesis.	2010 Jan 1	20028747
A novel inhibitor of the PI3K/Akt pathway based on the structure of inositol 1,3,4,5,6-pentakisphosphate.	2010 Jan 5	20051961
Cardiotoxicity of anticancer drugs: the need for cardio-oncology and cardio-oncological prevention.	2010 Jan 6	20007921
Deguelin suppresses cell proliferation via the inhibition of survivin expression and STAT3 phosphorylation in HTLV-1-transformed T cells.	2010 Mar	19781773
A comprehensive panel of three-dimensional models for studies of prostate cancer growth, invasion and drug responses.	2010 May 3	20454659
Differential chemosensitization of P-glycoprotein overexpressing K562/Adr cells by withaferin A and Siamois polyphenols.	2010 May 3	20438634
Deguelin--an inhibitor to tumor lymphangiogenesis and lymphatic metastasis by downregulation of vascular endothelial cell growth factor-D in lung tumor model.	2010 Nov 15	20162567
Deguelin promotes apoptosis and inhibits angiogenesis of gastric cancer.	2010 Oct	20811676
Inhibition of Cell Proliferation and MAP Kinase and Akt Pathways in Oral Squamous cell Carcinoma by Genistein and Biochanin A.	2010 Sep	18955325
Suppression of lung tumorigenesis by leucine zipper/EF hand-containing transmembrane-1.	2010 Sep 2	20824095
Anticancer efficacy of deguelin in human prostate cancer cells targeting glycogen synthase kinase-3 β/β-catenin pathway.	2011 Dec 15	21472727
Deguelin attenuates reperfusion injury and improves outcome after orthotopic lung transplantation in the rat.	2012	22745725
Induction of DNA damage by deguelin is mediated through reducing DNA repair genes in human non-small cell lung cancer NCI-H460 cells.	2012 Apr	22227970
Deguelin, an Akt inhibitor, down-regulates NF-κB signaling and induces apoptosis in colon cancer cells and inhibits tumor growth in mice.	2012 Nov	22623043
Deguelin, a selective silencer of the NPM1 mutant, potentiates apoptosis and induces differentiation in AML cells carrying the NPM1 mutation.	2015 Feb	25242579

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:42:17 GMT 2023` Edited by `admin` on `Fri Dec 15 19:42:17 GMT 2023`
Record UNII	K5Z93K66IE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEGUELIN

Common Name

English

(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

Common Name

English

DEGUELIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1745