Betulinic acid

SKU: orb1304966

Description

Betulinic acid (ALS-357) is a lupane-type triterpene derived from birch bark, exhibiting antiretroviral, antimalarial, and anti-inflammatory activities. Its anticancer potential, studied in vitro and in vivo, is linked to topoisomerase inhibition, making it a compound of interest for oncology and infectious disease research.

Research Area

Cell Biology

Key Properties

• CAS Number: 472-15-1
• MW: 456.72
• Purity: >98%
• Formula: C₃₀H₄₈O₃
• SMILES: C(O)(=O)[C@]12[C@@]([C@@]3([C@@](C)(CC1)[C@@]4(C)[C@](CC3)([C@]5(C)[C@@](CC4)(C(C)(C)[C@@H](O)CC5)[H])[H])[H])([C@H](C(C)=C)CC2)[H]
• Target: Parasite,Endogenous Metabolite,HIV Protease,Mitophagy,NF-κB,Apoptosis,Autophagy,Topoisomerase,Aminopeptidase
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).

Bioactivity

• Target IC50:
  Aminopeptidase N:7.3 μM|Topo I (eukaryotic):5 μM|HIV-1:1.4 μM(EC50)
• In Vivo:
  As an anti-melanoma agent, Betulinic acid inhibits the activity of aminopeptidase N (IC50: 7.3 μM). It exhibits anti-HIV properties by blocking HIV replication in H9 lymphocytes (EC50: 1.4 μM) and inhibiting the growth of uninfected H9 cells (IC50: 13 μM). Moreover, Betulinic acid shows potential as an anti-cancer candidate, suppressing the activity of eukaryotic topoisomerase I (IC50: 5 μM).
• In Vitro:
  In LNCaP cell cultures of athymic nude mice, Betulinic acid inhibits the growth of prostate cancer cells and tumors (xenografts). This inhibitory effect is partly due to the downregulation of protease-dependent Sp1/3/4 and several SP-regulated genes.

Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Topoisomerase, NF-kB, NFkB, NFκB, NF-κB, Nuclear factor-κB, Nuclear factor-kappaB, Mitochondrial Autophagy, Mitophagy, Lupatic acid, inhibit, Endogenous Metabolite, EndogenousMetabolite, Eukaryotic topoisomerase I, Inhibitor, Human immunodeficiency virus, HIVProtease, HIV-1, HIV Protease, HIV, Betulic acid, Betulinic acid, Apoptosis, Autophagy, ALS357, ALS-357, ALS 357, Aminopeptidase N

Compound Identifiers

PubChem CID

64971