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Details

Stereochemistry RACEMIC
Molecular Formula C15H12O3
Molecular Weight 240.254
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4'-HYDROXYFLAVANONE

SMILES

OC1=CC=C(C=C1)C2CC(=O)C3=CC=CC=C3O2

InChI

InChIKey=ZLHVIYHWWQYJID-UHFFFAOYSA-N
InChI=1S/C15H12O3/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-8,15-16H,9H2

HIDE SMILES / InChI

Molecular Formula C15H12O3
Molecular Weight 240.254
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

4’-Hydroxyflavanone is a flavonoid that can be found naturally in parsley, onions, berries, tea, and citrus fruits. 4-Hydroxyflavanone is an inhibitor of SREBP maturation and lipid synthesis, and 4-Hydroxyflavanone may have major potential as a pharmaceutical preparation against hepatic steatosis and dyslipidemia.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat acute toxicity (LD50) 2.8753 mol/kg
Route of Administration: Oral
In Vitro Use Guide
Test compounds (4-Hydroxyflavanone) were first assayed at 10 mkM for intrinsic activity using the [35S]GTP-gamma-S binding assay and CHO cell membrane homogenates that express the human muOR, deltaOR, or kappaOR. The subtype selective agonists (D-Ala2,MePhe4,Gly-ol5)enkephalin (DAMGO, muOR), (D-Pen2,D-Pen5)enkephalin (DPDPE, deltaOR), or U69,593 (kappaOR) were run as positive controls as appropriate. The CHO membranes were incubated in duplicate in 1.4 mL polypropylene tubes (Matrix Technologies, Hudson, NH) with positive control or test compound, 0.1 nM [35S]GTP-gamma-S, and 1 mkM GDP in 50 mM HEPES buffer (pH 7.4) at room temperature for 1 h, after which bound radioligand was separated from free via rapid vacuum filtration over GF-B filters with a Brandel Scientific (Gaithersburg, MD) 96-well harvester. Bound radioactivity was determined using a TopCount 12-detector instrument (Packard Instruments) using standard scintillation counting techniques. The data were normalized to samples containing vehicle (basal binding).
Substance Class Chemical
Record UNII
5K6L8O868Y
Record Status Validated (UNII)
Record Version