OROBOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O6
Molecular Weight	286.2363
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(O)=C2C(=O)C(=COC2=C1)C3=CC=C(O)C(O)=C3

InChI

InChIKey=IOYHCQBYQJQBSK-UHFFFAOYSA-N

InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H

HIDE SMILES / InChI

Molecular Formula	C15H10O6
Molecular Weight	286.2363
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Casein kinase I epsilon 5 Target ID: CHEMBL4937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/31222064	Inhibitor 8297		1.24 µM [IC50]
Sphingolipid delta(4)-desaturase DES1 5 Target ID: CHEMBL2021749 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30365230	Activator 1430

PubMed

Title	Date	PubMed
Effect of genistein analogs on oxygen radical production in leukocytes stimulated by unopsonized zymosan.	2001 Apr	11345702
Differential sensitization by orobol in proliferating and quiescent human ovarian carcinoma cells.	2001 Feb	11172601
Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo.	2001 Jun	11410004
New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa.	2004 Dec	15643558
Genistein and daidzein induce cell proliferation and their metabolites cause oxidative DNA damage in relation to isoflavone-induced cancer of estrogen-sensitive organs.	2004 Mar 9	14992594
Two pyranocoumarins from the seeds of Calophyllum polyanthum.	2004 Sep	15387670
Novel tempeh (fermented soyabean) isoflavones inhibit in vivo angiogenesis in the chicken chorioallantoic membrane assay.	2005 Mar	15877870
Identification of isolutein (lutein epoxide) as cis-antheraxanthin in orange juice.	2005 Nov 30	16302749
Activation of glutathione peroxidase via Nrf1 mediates genistein's protection against oxidative endothelial cell injury.	2006 Aug 4	16780800
Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.	2006 Aug 9	16881680
Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-beta-D-glucopyranosides.	2006 Jul 3	16643874
Characterization of mitochondria in cisplatin-resistant human ovarian carcinoma cells.	2006 Nov	17016583
The intracellular genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone mediates G2-M cell cycle arrest in cancer cells via modulation of the p38 signaling pathway.	2006 Oct 15	17015169
Inhibition of cellular proliferation by the genistein metabolite 5,7,3',4'-tetrahydroxyisoflavone is mediated by DNA damage and activation of the ATR signalling pathway.	2007 Dec 15	17976513
Differential regulation of the cytotoxicity activity of paclitaxel by orobol and platelet derived growth factor in human ovarian carcinoma cells.	2007 Jul	17549368
HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata.	2007 Nov	17696192
Comparison of genistein metabolism in rats and humans using liver microsomes and hepatocytes.	2008 Mar	18063284
Receptor binding and transactivation activities of red clover isoflavones and their metabolites.	2008 Nov	18809497
Red clover extract: a putative source for simultaneous treatment of menopausal disorders and the metabolic syndrome.	2008 Nov-Dec	18724264
The molecular basis of genistein-induced mitotic arrest and exit of self-renewal in embryonal carcinoma and primary cancer cell lines.	2008 Oct 10	18847459
Regioselective hydroxylation of isoflavones by Streptomyces avermitilis MA-4680.	2009 Jul	19577190
[Studies on chemical constituents from stems of Cudrania tricuspidata].	2009 May	19685745
Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro.	2010 Jan	19637114
Inhibitory effects of orobol 7-O-D-glucoside from banaba (Lagerstroemia speciosa L.) on human rhinoviruses replication.	2010 Jul	20497313
Red clover extract: a source for substances that activate peroxisome proliferator-activated receptor alpha and ameliorate the cytokine secretion profile of lipopolysaccharide-stimulated macrophages.	2010 Mar	20142789

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:59:26 GMT 2023` Edited by `admin` on `Fri Dec 15 18:59:26 GMT 2023`
Record UNII	LU8UZM1T51
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OROBOL

Common Name

English

3',4',5,7-TETRAHYDROXYISOFLAVONE

Common Name

English

ISOFLAVONE, 3',4',5,7-TETRAHYDROXY-

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-(3,4-DIHYDROXYPHENYL)-

Systematic Name

English

NSC-678114

Code

English

ISOLUTEOLIN

Common Name

English

Code System Code Type Description

CAS

480-23-9