CAS 480-41-1|Naringenin|naringenin|(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one|4',5,7-trihydroxyflavanone|Naringenin|(R)-naringenin|(2R)-naringenin|(+)-(2R)-5,7-dihydrox...

General Information

Structure

Molecular Formula

C₁₅H₁₂O₅

Molecular Mass

272.25278

Exact Mass

272.06847348

Charge

InChI

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

InChIKey

FTVWIRXFELQLPI-ZDUSSCGKSA-N

Canonic Smiles

Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O

Isomeric Smiles

c1c(cc(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O)O

Calculated Properties

JChem

LogD (pH = 7.4)

2.70

LogD (pH = 5.5)

2.83

Log P

2.84

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.86

Polar Surface Area

86.99

Polarizability

27.32

Molar Refractivity

71.29

LOG S

-2.67

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Naringenin4',5,7-trihydroxyflavanoneNaringenin(R)-naringenin(+)-(2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone(2R)-naringenin

IUPAC name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one (2R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

IUPAC Traditional name

naringenin (-)-naringenin

Names and Identifiers

Registration numbers

DrugBank ID

DB03467

Chemspider ID

388383

Unique Ingredient Identifier

CAS Number

CHEMBL

Wikipedia Title

PubChem CID

PubChem SID

1609665874650804350139421

BRENDA Database

1.14.20.61.14.20.51.14.20.4

UniProt Database

Q7XZQ6

BRENDA Ligand Database

Protein Data Bank

Reaxys Registry

Beilstein Number

BKMS React Database

MetaCyc Database

CHEBI ID

SureChEMBL Database

Registration numbers

Properties

Product Information

Free Base

98.0

Safety Information

-20°C

Physical Property

Powder

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB03467

Drug information: experimental

Selleck Chemicals

S2394

Research Area: Inflammation
Biological Activity:
Naringenin is a flavonoid that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulator. Naringenin is the predominant flavanone in grapefruit. This substance has also been shown to reduce oxidative damage to DNA in vitro. Naringenin found in grapefruit juice has been shown to have an inhibitory effect on the human cytochrome P450 isoform CYP1A2, which can change pharmacokinetics in a human (or orthologous) host of several popular agents in an adverse manner, even resulting in carcinogens of otherwise harmless substances. [1]References on Naringenin[1] http://en.wikipedia.org/wiki/Naringenin, , [2] www.scielo.br/scielo.php?script=sci_arttext&pid=S1516, ,

The (R)-enantiomer of naringenin.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Naringenin

References

Bioactivity