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Prunin

CAT: 0931-TN2111-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-TN2111-01Size:1 mg
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CAS Number
529-55-5
Target
Phosphatase, Anti-infection, Virus Protease
Related Pathways
Metabolism, Microbiology/Virology
Purity
0.9962
Bioactivity
Prunin (Naringenin 7-0-glucoside) possesses anti-diabetic, and anti-abacterial properties, it can inhibit protein tyrosine phosphatase 1B (PTP1B) and stimulate glucose uptake in insulin-resistant HepG2 cells; it also can stimulate growth of Pseudomonas aeruginosa and different Bacilllus sp. Prunin exhibits a markedly enhanced solubility compared to naringenin and naringin while maintaining the in vitro inhibition of HMG-CoA reductase.
Smiles
OC[C@H]1O[C@@H](Oc2cc(O)c3C(=O)C[C@@H](Oc3c2)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Molecular Formula
C21H22O10
Molecular Weight
434.39
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Prunin

Naringenin 7-O-beta-D-glucoside is a flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a metabolite, an antibacterial agent, a hypoglycemic agent and an antilipemic drug. It is a flavanone 7-O-beta-D-glucoside, a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a dihydroxyflavanone and a monosaccharide derivative. It is functionally related to a (S)-naringenin.

CAS Number529-55-5
PubChem CID92794
IUPAC Name(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Molecular FormulaC21H22O10
Molecular Weight434.4
XLogP0.6
Topological Polar Surface Area166
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count31
Formal Charge0
Complexity623
SMILES
C1[C@H](OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O
InChI
InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1
InChIKey
DLIKSSGEMUFQOK-SFTVRKLSSA-N
Chemical Structure
2D Structure
2D structure of Prunin
CAS: 529-55-5
CID: 92794
Formula: C21H22O10
MW: 434.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight434.4
XLogP30.6
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass434.12129689
Monoisotopic Mass434.12129689
Topological Polar Surface Area166 Ų
Heavy Atom Count31
Formal Charge0
Complexity623
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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