RETUSIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18O7
Molecular Weight	358.342
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C(=O)C(OC)=C(O2)C3=CC(OC)=C(OC)C=C3)C(O)=C1

InChI

InChIKey=HHGPYJLEJGNWJA-UHFFFAOYSA-N

InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C19H18O7
Molecular Weight	358.342
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26080742 | https://www.ncbi.nlm.nih.gov/pubmed/26058603 | https://www.ncbi.nlm.nih.gov/pubmed/10374246

Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata, in Dalbergia retusa and in Millettia nitida. Retusin exhibited potent free-radical-scavenging capacity as well as efficient inhibition of cellular melanogenesis, suggesting that it is a valuable hit compound with potential for advanced cosmeceutical development. Retusin showed efficient inhibition both of cellular melanin formation and anti-tyrosinase activity in B16F10 melanocytes. Retusin exhibited an anti-emetic effect in chick model.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Tyrosinase 41 Target ID: CHEMBL3318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26080742	Inhibitor 8297	50.9 µM [IC50]
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26080742	Inhibitor 8297
ATP-binding cassette sub-family G member 2 16 Target ID: CHEMBL5393 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21354800 \| https://www.ncbi.nlm.nih.gov/pubmed/23851114	Inhibitor 8297	390.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting and nausea 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10374246	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of different flavonoids on collagen synthesis in human fibroblasts.	2006 Mar	16642409
Inhibitory effects of quercetin derivatives on phosphodiesterase isozymes and high-affinity [(3) H]-rolipram binding in guinea pig tissues.	2008 Oct	18264679
Effects of compounds from Kaempferia parviflora on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha productions in RAW264.7 macrophage cells.	2008 Oct 30	18725283
Anti-inflammatory mechanism of Kaempferia parviflora in murine macrophage cells (RAW 264.7) and in experimental animals.	2009 Jul 30	19439175

Patents

Sample Use Guides

In Vivo Use Guide

Retusin inhibited emetic action of copper sulfate at two doses of 20 mg/kg and 50 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

Retusin inhibited mushroom tyrosinase activity with the IC50 value of 50.9 uM at 30 min.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:09:49 GMT 2023` Edited by `admin` on `Fri Dec 15 18:09:49 GMT 2023`
Record UNII	M8591903SD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RETUSIN

Common Name

English

2-(3,4-DIMETHOXYPHENYL)-5-HYDROXY-3,7-DIMETHOXY-4H-CHROMEN-4-ONE

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIMETHOXYPHENYL)-5-HYDROXY-3,7-DIMETHOXY-

Systematic Name

English

QUERCETIN 3,3',4',7-O-TETRAMETHYL ETHER

Common Name

English

3,3',4',7-TETRA-O-METHYLQUERCETIN

Common Name

English

FLAVONE, 5-HYDROXY-3,3',4',7-TETRAMETHOXY-

Systematic Name

English

3,3',4',7-TETRAMETHYLQUERCETIN

Common Name

English

5-HYDROXY-3,7,3',4'-TETRAMETHOXYFLAVONE

Systematic Name

English

QUERCETIN 3,7,3',4'-TETRAMETHYL ETHER

Common Name

English

NSC-61837

Code

English

NSC-618937

Code

English

HYDROXY-3,3',4',7-TETRAMETHOXYFLAVONE, 5-

Systematic Name

English

5-HYDROXY-3,3',4',7-TETRAMETHOXYFLAVONE

Systematic Name

English

Code System Code Type Description

NSC

61837