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Brevilin A (Standard)

CAT: 0804-HY-N2959R-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2959R-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Brevilin A (Standard) is the analytical standard of Brevilin A. This product is intended for research and analytical applications. Brevilin A is an orally active STAT3/JAK inhibitor (STAT3 IC50= 10.6 μM) . Brevilin A shows anti-tumor activity, anti-proliferative activity to cancer cells, and can induce apoptosis and autophagy[1][2].
CAS Number
16503-32-5
UNSPSC
12352005
Target
Apoptosis; Autophagy; JAK; Reference Standards; STAT
Type
Reference Standards
Related Pathways
Apoptosis; Autophagy; Epigenetics; JAK/STAT Signaling; Others; Protein Tyrosine Kinase/RTK; Stem Cell/Wnt
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/brevilin-a-standard.html
Smiles
C/C=C(C)\C(O[C@H]1[C@@]([C@@H]2C)([H])[C@@](OC2=O)([H])C[C@@H](C)[C@@]3([H])[C@]1(C(C=C3)=O)C)=O
Molecular Formula
C20H26O5
Molecular Weight
346.42
References & Citations
[1]Chen X, et al. Brevilin A, a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells. PLoS One. 2013 May 21;8 (5) :e63697.|[2]You P, et al. Brevilin A induces apoptosis and autophagy of colon adenocarcinoma cell CT26 via mitochondrial pathway and PI3K/AKT/mTOR inactivation. Biomed Pharmacother. 2018 Feb;98:619-625.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Brevilin A

(3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8-trimethyl-2,5-dioxo-3H,3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate has been reported in Arnica longifolia with data available.

CAS Number16503-32-5
PubChem CID12302076
IUPAC Name[(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate
Molecular FormulaC20H26O5
Molecular Weight346.4
XLogP2.3
Topological Polar Surface Area69.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count25
Formal Charge0
Complexity676
SMILES
C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H](C(=O)O[C@@H]2C[C@H]([C@H]3[C@]1(C(=O)C=C3)C)C)C
InChI
InChI=1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1
InChIKey
KUPPZVXLWANEJJ-UXPPPGSFSA-N
Chemical Structure
2D Structure
2D structure of Brevilin A
CAS: 16503-32-5
CID: 12302076
Formula: C20H26O5
MW: 346.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight346.4
XLogP32.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass346.17802393
Monoisotopic Mass346.17802393
Topological Polar Surface Area69.7 Ų
Heavy Atom Count25
Formal Charge0
Complexity676
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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