LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

alpha-Amyrin

Systematic Name

Synonyms

LM ID

LMPR0106170001

Formula

C₃₀H₅₀O

Exact Mass

Calculate m/z

426.386165

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

α-Amyrin is a triterpenoid that has been found in B. copallifera and has diverse biological activities.^1,2,3,4 It inhibits HIV-1 reverse transcriptase (IC50 = 3.3 µM).¹ α-Amyrin inhibits the proliferation of B16 2F2 melanoma cells and LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages (IC50s = 50 and 8.98 µM, respectively).^2,3 It reduces myeloperoxidase (MPO) activity, indicating a decrease in polymorphonuclear leukocyte (PMN) infiltration, and ear edema induced by phorbol 12-myristate 13-acetate (TPA) in mice (ID50s = 0.45 and 0.31 mg/ear, respectively).⁴

This information has been provided by Cayman Chemical

References

1. Romero-Estrada, A., Maldonado-Magaña, A., González-Christen, J., et al. Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera. BMC Complement. Altern. Med. 16(1), 422 (2016).

2. Akihisa, T., Ogihara, J., Kato, J., et al. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids 36(5), 507-512 (2001).

3. Hata, K., Hori, K., and Takahashi, S. Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line. J. Nat. Prod. 65(5), 645-648 (2002).

4. Otuki, M.F., Vieira-Lima, F., Malheiros, Â., et al. Topical antiinflammatory effects of the ether extract from Protium kleinii and α-amyrin pentacyclic triterpene. Eur. J. Pharmacol. 507(1-3), 253-259 (2005).

String Representations

InChiKey (Click to copy)

FSLPMRQHCOLESF-SFMCKYFRSA-N

InChi (Click to copy)

InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-25,31H,10-18H2,1-8H3/t19-,20+,22+,23-,24+,25+,27-,28+,29-,30-/m1/s1

SMILES (Click to copy)

[C@@]12(C)CC[C@@]3([H])C(C)(C)[C@H](CC[C@]3(C)[C@@]1([H])CC=C1[C@]3([H])[C@@H](C)[C@@H](CC[C@@]3(CC[C@@]21C)C)C)O