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

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
Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent.	1997 Aug 15	9270009
Review article number 135 biosynthesis in the rotenoid group of natural products: applications of isotope methodology.	1998 Nov 20	11711058
Deguelin inhibits the growth of colon cancer cells through the induction of apoptosis and cell cycle arrest.	2002 Dec	12460790
Discovery of cancer preventive agents from natural products: from plants to prevention.	2002 Nov	12354359
Deguelin suppresses the formation of carcinogen-induced aberrant crypt foci in the colon of CF-1 mice.	2003 Mar 10	12532413
Cancer chemopreventive activity of rotenoids from Derris trifoliata.	2004 Jun	15229812
Efficacy of deguelin and silibinin on benzo(a)pyrene-induced lung tumorigenesis in A/J mice.	2005 Dec	16354587
Regulating expressions of cyclin D1, pRb, and anti-cancer effects of deguelin on human Burkitt's lymphoma Daudi cells in vitro.	2005 Jul	15960896
Effect of deguelin on UVB-induced skin carcinogenesis.	2005 Jun	16041863
Cross-talk between the two divergent insulin signaling pathways is revealed by the protein kinase B (Akt)-mediated phosphorylation of adapter protein APS on serine 588.	2005 Nov 11	16141217
Deguelin regulates nuclear pore complex proteins Nup98 and Nup88 in U937 cells in vitro.	2005 Oct	16174445
Deguelin inhibits expression of IkappaBalpha protein in Raji and U937 cells.	2006 Apr	16539850
Soluble Fas ligand inhibits angiogenesis in rheumatoid arthritis.	2007	17459170
The phosphoinositide 3-kinase pathway in human cancer: genetic alterations and therapeutic implications.	2007 Aug	19384426
[Effect of deguelin on proliferation and apoptosis of lymphoma Daudi cells and its mechanism].	2007 Mar	17649631
Mechanism of uptake and retention of F-18 BMS-747158-02 in cardiomyocytes: a novel PET myocardial imaging agent.	2007 Nov-Dec	18022104
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
Involvement of SRC-3 in deguelin-induced apoptosis in Jurkat cells.	2009 Jun	19365708
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
Optimising resolution for a preparative separation of Chinese herbal medicine using a surrogate model sample system.	2009 Jun 26	19447397
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
Deguelin suppresses cell proliferation via the inhibition of survivin expression and STAT3 phosphorylation in HTLV-1-transformed T cells.	2010 Mar	19781773
Deguelin, a selective silencer of the NPM1 mutant, potentiates apoptosis and induces differentiation in AML cells carrying the NPM1 mutation.	2015 Feb	25242579

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