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

• ChemBase ID: 3143
• Molecular Formular: C15H12O5
• Molecular Mass: 272.25278
• Monoisotopic Mass: 272.06847348
• SMILES: c1c(cc(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: naringenin
• Synonyms: Naringenin; 4',5,7-trihydroxyflavanone; Naringenin

Database IDs

• CAS Number: 480-41-1
• PubChem SID: 46508043; 160966587
• PubChem CID: 932; 439246
• CHEMBL: 9352
• Chemspider ID: 388383
• DrugBank ID: DB03467
• Unique Ingredient Identifier: HN5425SBF2
• Wikipedia Title: Naringenin

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.856156
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.833213
• LogD (pH = 7.4): 2.7041416
• Log P: 2.835108
• Molar Refractivity: 71.2898 cm^3
• Polarizability: 27.291258 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -3.11
• Solubility (Water): 2.14e-01 g/l

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 98.0
• Salt Data: Free Base

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, ,

REFERENCES

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