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Description: Betulinic acid (also known as ALS-357; LS-357; Mairin; Lupatic acid; Betulic acid) is a naturally occuring pentacyclic triterpenoid extracted from Syzigium claviflorum that displays anti-HIV and antitumor activity. Betulinic acid acts as an inhibitor of HIV-1 with an EC50 of 1.4 u M. Betulinic acid selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic acid also displays TGR5 agonist activity (EC50 =1.04 uM).
References: Planta Med. 1998 Oct; 64(7):655-7; J Nat Prod. 1994 Feb; 57(2):243-7.
Chemical Name: (1R, 3aS, 5aR, 5bR, 7aR, 9S, 11aR, 11bR, 13aR, 13bR)-9-hydroxy-5a, 5b, 8, 8, 11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
InChi Key: QGJZLNKBHJESQX-FZFNOLFKSA-N
InChi Code: 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 Code: O=C([C]1(CC[CH]2C(C)=C)[C]2([H])[C]3([H])CC[C]4([H])[C]5(C)CC[CH](O)C(C)(C)[C]5([H])CC[C]4(C)[C]3(C)CC1)O
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