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Structure Database (LMSD)

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Common Name

Betulinic acid

Systematic Name

3β-Hydroxy-lup-20(29)-en-28-oic acid

Synonyms

LM ID

LMPR0106140004

Formula

C₃₀H₄₈O₃

Exact Mass

Calculate m/z

456.360345

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Betulinic acid is a natural plant triterpenoid that is structurally related to mammalian bile acids. It is an agonist of the G protein-coupled bile acid receptor TGR5 (EC50 = 1 µM), which might be linked with its ability to alter gene expression and fatty liver development in cells and mice given ethanol.^1,2,3 Betulinic acid also reduces NF-κB signaling and expression of microRNA-33 in LPS-treated macrophages, increasing levels of the ATP-binding cassette (ABC) cholesterol transporter ABCA1.4 It also inhibits replication of HIV-1 (IC50 = 1.4 µM) and has cytotoxic effects against cancer cells.^3,5

This information has been provided by Cayman Chemical

References

1. Mullauer, F.B., Kessler, J.H., and Medema, J.P. Betulin is a potent anti-tumor agent that is enhanced by cholesterol. PLoS One 4(4), (2009).

2. Kashiwada, Y., Hashimoto, F., Cosentino, L.M., et al. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J. Med. Chem. 39(5), 1016-1017 (1996).

3. Wan, Y., Jiang, S., Lian, L.H., et al. Betulinic acid and betulin ameliorate acute ethanol-induced fatty liver via TLR4 and STAT3 in vivo and in vitro. Int. Immunopharmacol. 17(2), 184-190 (2013).

4. Zhao, G.J., Tang, S.L., Lv, Y.C., et al. Antagonism of betulinic acid on LPS-mediated inhibition of ABCA1 and cholesterol efflux through inhibiting nuclear factor-kappaB signaling pathway and miR-33 expression. PLoS One 8(9), e474782 (2013).

5. Genet, C., Strehle, A., Schmidt, C., et al. Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: Potential impact in diabetes. J. Med. Chem. 53(1), 178-190 (2010).

String Representations

InChiKey (Click to copy)

QGJZLNKBHJESQX-FZFNOLFKSA-N

InChi (Click to copy)

InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

SMILES (Click to copy)

C1[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])CC[C@@]2([C@@]4([C@](CC[C@@]32C)(C(O)=O)CC[C@H]4C(C)=C)[H])[H])C(C)(C)[C@@H](O)C1