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Kahweol acetate

CAT: 0804-HY-N7210Size: InquireDry Ice: NoHazardous: No
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CAS Number
81760-47-6
UNSPSC Description
Kahweol acetate, a bioactive compound found in coffee, has been identified for its potent anti-cancer properties, particularly in inhibiting the proliferation and migration of prostate cancer cells. Alongside cafestol, it shows dose-dependent effects in suppressing tumor growth and metastasis in both in vitro and in vivo studies. Mechanistically, kahweol acetate and cafestol induce apoptosis, inhibit epithelial-mesenchymal transition, and reduce androgen receptor activity, especially in androgen receptor-positive cells. They also downregulate chemokine receptors CCR2 and CCR5, crucial for cancer progression, without altering their ligand levels. These findings suggest that kahweol acetate, in combination with cafestol, may serve as promising therapeutic agents against prostate cancer[1].
Target Antigen
Apoptosis
Type
Natural Products
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
cancer
Assay Protocol
https://www.medchemexpress.com/kahweol-acetate.html
Smiles
OC[C@@]([C@]1([H])CC2)(OC(C)=O)C[C@](CC[C@@]34[H])(C1)[C@]2([H])[C@]3(C)C=CC5=C4C=CO5
Molecular Weight
356.46
References & Citations
[1]Coffee diterpenes kahweol acetate and cafestol synergistically inhibit the proliferation and migration of prostate cancer cells
Shipping Conditions
Room temperature
Clinical Information
No Development Reported

Chemical Information

Kahweol Acetate

found in coffee; structure given in first source

CAS Number81760-47-6
PubChem CID157914
IUPAC Name[(4S,12S,13R,16R,17R)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-yl]methyl acetate
Molecular FormulaC22H28O4
Molecular Weight356.5
XLogP4
Topological Polar Surface Area59.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Heavy Atom Count26
Formal Charge0
Complexity644
SMILES
CC(=O)OC[C@]1(CC23CC[C@@H]4C5=C(C=C[C@]4([C@@H]2CC[C@@H]1C3)C)OC=C5)O
InChI
InChI=1S/C22H28O4/c1-14(23)26-13-22(24)12-21-9-5-17-16-7-10-25-18(16)6-8-20(17,2)19(21)4-3-15(22)11-21/h6-8,10,15,17,19,24H,3-5,9,11-13H2,1-2H3/t15-,17-,19+,20-,21?,22+/m1/s1
InChIKey
OJLWVPDNBQAHRT-PCEBFAEYSA-N
Chemical Structure
2D Structure
2D structure of Kahweol Acetate
CAS: 81760-47-6
CID: 157914
Formula: C22H28O4
MW: 356.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight356.5
XLogP34
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass356.19875937
Monoisotopic Mass356.19875937
Topological Polar Surface Area59.7 Ų
Heavy Atom Count26
Formal Charge0
Complexity644
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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