ROBINETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O7
Molecular Weight	302.2357
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C=C1)C(=O)C(O)=C(O2)C3=CC(O)=C(O)C(O)=C3

InChI

InChIKey=SOEDEYVDCDYMMH-UHFFFAOYSA-N

InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6360409 | https://www.ncbi.nlm.nih.gov/pubmed/17951065

Robinetin is a bioactive plant flavonol. Robinetin inhibited the mutagenic activity resulting from the metabolic activation of benzo[a]-pyrene and (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]-pyrene by rat liver microsomes.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Ornithine decarboxylase 15 Target ID: CHEMBL2840 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3708757	Modulator 828
Mitochondrial complex I (NADH dehydrogenase) 11 Target ID: CHEMBL2363065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8117326	Inhibitor 8297
Multidrug resistance-associated protein 1 15 Target ID: CHEMBL3004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15670588	Inhibitor 8297	5.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3708757	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.	1996 Dec	8987091
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.	2005 Feb 15	15670588
Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP.	2005 Mar-Apr	15796208
Antimicrobial activity of flavonoids.	2005 Nov	16323269
Allelopathic potential of Robinia pseudo-acacia L.	2005 Sep	16132219
An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers.	2006 Dec 1	16997339
Effect of beta-cyclodextrin nanocavity confinement on the photophysics of robinetin.	2007 Dec 14	17951065
Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation.	2010 Jan 21	19914085

Patents

Sample Use Guides

In Vivo Use Guide

Examination of both urine extracts from robinetin-fed rats (200mg/rat) and ether extracts ofrobinetin incubation mixtures (10mg/tube) revealed the presence of large amounts of unchanged robinetin.

Route of Administration: Oral

In Vitro Use Guide

Robinetin inhibited MRP2 activity more than 50% at 25 uM concentration.

Name

Type

Language

ROBINETIN

Common Name

English

3,7,3',4',5'-PENTAHYDROXYFLAVONE

Systematic Name

English

FLAVONE, 3,3',4',5',7-PENTAHYDROXY-

Systematic Name

English

NORKANUGIN

Common Name

English

NSC-656274

Code

English

4H-1-BENZOPYRAN-4-ONE, 3,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-

Systematic Name

English

3,3',4',5',7-PENTAHYDROXYFLAVONE

Systematic Name

English

NSC-407331

Code

English

3,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-4-BENZOPYRONE

Systematic Name

English

5-HYDROXYFISETIN

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID30197654