A pentacyclic triterpenoid with diverse biological activities
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Isomer(s)
10072Ursolic Acid
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3-epi Ursolic Acid

Item No. 36528

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3α-hydroxy-urs-12-en-28-oic acid
CAS Number
989-30-0
Synonyms
  • 3-Epiursolic Acid
  • α-Ursolic Acid
Molecular Formula
C30H48O3
Formula Weight
456.7
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
OC([C@]12[C@]([C@H]([C@@H](CC2)C)C)([H])C3=CC[C@@]([C@@]4([C@@](C(C)([C@@H](CC4)O)C)([H])CC5)C)([H])[C@]5(C)[C@@]3(CC1)C)=O
InChi Code
InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23-,24+,27+,28-,29-,30+/m1/s1
InChi Key
WCGUUGGRBIKTOS-XHINXETDSA-N
Origin
Plant/Eriobotrya japonica (Thunb.) Lindl.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    3-epi Ursolic acid is a pentacyclic triterpenoid that has been found in M. lingua and has diverse biological activities.1,2,3,4 It inhibits glycogen phosphorylase and cathepsin L but not cathepsin B (IC50s = 19, 6.5, and >250 µM, respectively).1,2 3-epi Ursolic acid (20-50 µM) inhibits entry of bovine parainfluenza virus 3 into MDBK cells.3 It also inhibits the proliferation of MCF-7 breast cancer cells (IC50 = 18.6 µg/ml).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wen, X., Sun, H., Liu, J., et al. Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: Synthesis, structure-activity relationships, and X-ray crystallographic studies. J. Med. Chem. 51(12), 3540-3554 (2008).

    2. Ramalho, S.D., De Sousa, L.R.F., Nebo, L., et al. Triterpenoids as novel natural inhibitors of human cathepsin L. Chem. Biodivers. 11(9), 1354-1363 (2014).

    3. Pan, W., Hui, N., Wang, H., et al. Entry of bovine parainfluenza virus type 3 into MDBK cells occurs via clathrin-mediated endocytosis and macropinocytosis in a acid-dependent manner. Vet. Microbiol. 259, 109148 (2021).

    4. Qamar, K.A., Dar, A., Siddiqui, B.S., et al. Antiproliferative effects of Ocimum basilicum methanolic extract and fractions, aleanolic acid and 3-epi-ursolic acid. Curr. Tradit. Med. 6(2), 134-146 (2020).