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Bilobetin

CAT: 0804-HY-N2118-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2118-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Bilobetin, an active component of Ginkgo biloba, can reduce blood lipids and improve the effects of insulin. Bilobetin ameliorated insulin resistance, increased the hepatic uptake and oxidation of lipids, reduced very-low-density lipoprotein triglyceride secretion and blood triglyceride levels, enhanced the expression and activity of enzymes involved in β-oxidation and attenuated the accumulation of triglycerides and their metabolites in tissues. Bilobetin also increased the phosphorylation, nuclear translocation and activity of PPARα accompanied by elevated cAMP level and PKA activity[1].
CAS Number
521-32-4
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Akt; ERK; p38 MAPK; PKA; PPAR
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; MAPK/ERK Pathway; Metabolic Enzyme/Protease; PI3K/Akt/mTOR; Stem Cell/Wnt; TGF-beta/Smad; Vitamin D Related/Nuclear Receptor
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/bilobetin.html
Purity
99.71
Solubility
DMSO : 250 mg/mL (ultrasonic)
Smiles
O=C1C=C(C2=CC=C(O)C=C2)OC3=C(C4=CC(C5=CC(C6=C(O)C=C(O)C=C6O5)=O)=CC=C4OC)C(O)=CC(O)=C13
Molecular Formula
C31H20O10
Molecular Weight
552.48
Precautions
H302, H315, H319, H335
References & Citations
[1]Kou XH, et al. Bilobetin ameliorates insulin resistance by PKA-mediated phosphorylation of PPARα in rats fed a high-fat diet. Br J Pharmacol. 2012 Apr;165 (8) :2692-706.|[2]Wang Q, et al. Bilobetin induces kidney injury by influencing cGMP-mediated AQP-2 trafficking and podocyte cell cycle arrest. Phytomedicine. 2019 Nov;64:153073. |[3]Negm WA, et al. The Mechanistic Perspective of Bilobetin Protective Effects against Cisplatin-Induced Testicular Toxicity: Role of Nrf-2/Keap-1 Signaling, Inflammation, and Apoptosis. Biomedicines. 2022 May 13;10 (5) :1134|[4]Han Ki Lee, et al. Bilobetin induces apoptosis in human hepatocellular carcinoma cells via ROS level elevation and inhibition of CYP2J2.Arabian Journal of Chemistry. Volume 16, Issue 9, September 2023, 105094. |[5]Wang C, et al. Inhibition of Insulin-Like Growth Factor-1–Induced Sebum Production by Bilobetin in Cultured Human Sebocytes [J]. Annals of Dermatology, 2019, 31 (3) : 294.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
PKA; PPARα

Chemical Information

Bilobetin

Bilobetin is a flavonoid oligomer.

CAS Number521-32-4
PubChem CID5315459
IUPAC Name8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Molecular FormulaC31H20O10
Molecular Weight552.5
XLogP5.4
Topological Polar Surface Area163
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count41
Formal Charge0
Complexity1060
SMILES
COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)O
InChI
InChI=1S/C31H20O10/c1-39-24-7-4-15(26-12-22(37)29-19(34)9-17(33)10-27(29)40-26)8-18(24)28-20(35)11-21(36)30-23(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3
InChIKey
IWEIJEPIYMAGTH-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Bilobetin
CAS: 521-32-4
CID: 5315459
Formula: C31H20O10
MW: 552.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight552.5
XLogP35.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass552.10564683
Monoisotopic Mass552.10564683
Topological Polar Surface Area163 Ų
Heavy Atom Count41
Formal Charge0
Complexity1060
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
573969Bilobetin

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