Vinaxanthone

Vinaxanthone (SM-345431) is a potent and selective semaphorin3A, phospholipase C (PLC) and FabI inhibitor, with IC50s of 0.1-0.2 μM and 0.9 mM for semaphorin3A and FabI. Vinaxanthone inhibits the substrate (t-o-NAC thioester) and the cofactor (NADPH) with Kis of 3.1 μM and 1.0 μM, respectively. Vinaxanthone can be used to handle infections caused by multidrug-resistant pathogens[1][2][3].

Product Specifications

CAS Number

[133293-89-7]

Product Name Alternative

SM-345431

UNSPSC

12352005

Target

Bacterial; Phospholipase

Type

Natural Products

Related Pathways

Anti-infection; Metabolic Enzyme/Protease

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/vinaxanthone.html

Purity

98.77

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C(C(O)=C(C=C1OC=C2C3=C(C(C)=O)C4=C(C(C5=C(C(O)=O)C(O)=C(O)C=C5O4)=O)C=C3C(C)=O)O)=C1C2=O)O

Molecular Formula

C28H16O14

Molecular Weight

576.42

References & Citations

[1]Masahiro Aoki, et al. Structure of a novel phospholipase C inhibitor, vinaxanthone (Ro 09-1450), produced by penicillium vinaceum. Tetrahedron Letters. 1991, 32 (36) :4737-4740. |[2]Liang Zhang, et al. Rewiring of regenerated axons by combining treadmill training with semaphorin3A inhibition. Mol Brain. 2014 Mar 10; 7:14. |[3]Zheng CJ, et al. Vinaxanthone, a new FabI inhibitor from Penicillium sp. J Antimicrob Chemother. 2009 May;63 (5) :949-53.|[4]Omoto M, Yoshida S, Miyashita H, Kawakita T, Yoshida K, Kishino A, Kimura T, Shibata S, Tsubota K, Okano H, Shimmura S. The semaphorin 3A inhibitor SM-345431 accelerates peripheral nerve regeneration and sensitivity in a murine corneal transplantation model. PLoS One. 2012;7 (11) :e47716. |[5]Sang Y, et al. Semaphorin3A-Inhibitor Ameliorates Doxorubicin-Induced Podocyte Injury. Int J Mol Sci. 2020 Jun 8;21 (11) :4099. |[6]Sang Y, et al. Semaporin3A inhibitor ameliorates renal fibrosis through the regulation of JNK signaling. Am J Physiol Renal Physiol. 2021 Dec 1;321 (6) :F740-F756.