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Cudraflavone B

CAT: 0804-HY-N10009Size: 1 EachDry Ice: NoHazardous: No
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Description
Cudraflavone B is a prenylated flavonoid with anti-inflammatory and anti-tumor properties. Cudraflavone B is also a dual inhibitor of COX-1 and COX-2. Cudraflavone B blocks the translocation of nuclear factor κB (NF-κB) from the cytoplasm to the nucleus in macrophages. Thus, Cudraflavone B inhibits tumor necrosis factor α (TNFα) gene expression and secretion. Cudraflavone B also triggers the mitochondrial apoptotic pathway, activates NF-κB, the MAPK p38, and ERK, and induced the expression of SIRT1. Thus Cudraflavone B inhibits the growth of human oral squamous cell carcinoma cells[1][2].
CAS Number
19275-49-1
UNSPSC
12352005
Target
COX; ERK; NF-κB; p38 MAPK; Sirtuin; TNF Receptor
Type
Natural Products
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; MAPK/ERK Pathway; NF-κB; Stem Cell/Wnt
Applications
COVID-19-anti-virus
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/cudraflavone-b.html
Solubility
10 mM in DMSO
Smiles
O=C1C2=C(C3=C(C=C2OC(C4=C(O)C=C(O)C=C4)=C1C/C=C(C)\C)OC(C)(C)C=C3)O
Molecular Formula
C25H24O6
Molecular Weight
420.45
References & Citations
[1]Hošek J, et al. Natural compound cudraflavone B shows promising anti-inflammatory properties in vitro. J Nat Prod. 2011 Apr 25;74 (4) :614-9. |[2]Lee HJ, et al. Growth inhibition and apoptosis-inducing effects of cudraflavone B in human oral cancer cells via MAPK, NF-κB, and SIRT1 signaling pathway. Planta Med. 2013 Sep;79 (14) :1298-306.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
COX-1; COX-2; ERK; NF-κB; p38 MAPK; SIRT1; TNFRSF1A/CD120a

Chemical Information

Cudraflavone B

Cudraflavone B is an extended flavonoid that consists of a pyranochromane skeleton that is 2H,6H-pyrano[3,2-g]chromen-6-one substituted by geminal methyl groups at position 2, a 2,4-dihydroxyphenyl group at position 8, a hydroxy group at position 5 and a prenyl group at position 7. Isolated from Morus alba and Morus species it exhibits anti-inflammatory activity. It has a role as an anti-inflammatory agent and a plant metabolite. It is a trihydroxyflavone, an extended flavonoid and a pyranochromane.

CAS Number19275-49-1
PubChem CID5319925
IUPAC Name8-(2,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
Molecular FormulaC25H24O6
Molecular Weight420.5
XLogP5.5
Topological Polar Surface Area96.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Heavy Atom Count31
Formal Charge0
Complexity805
SMILES
CC(=CCC1=C(OC2=CC3=C(C=CC(O3)(C)C)C(=C2C1=O)O)C4=C(C=C(C=C4)O)O)C
InChI
InChI=1S/C25H24O6/c1-13(2)5-7-17-23(29)21-20(30-24(17)15-8-6-14(26)11-18(15)27)12-19-16(22(21)28)9-10-25(3,4)31-19/h5-6,8-12,26-28H,7H2,1-4H3
InChIKey
XIWCDUHPYMOFIL-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Cudraflavone B
CAS: 19275-49-1
CID: 5319925
Formula: C25H24O6
MW: 420.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight420.5
XLogP35.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass420.15728848
Monoisotopic Mass420.15728848
Topological Polar Surface Area96.2 Ų
Heavy Atom Count31
Formal Charge0
Complexity805
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

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