Record Information
public_id FDB001532
Chemical Information
name Betulinic acid
description Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis.; Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53.
cas_number 472-15-1
Properties
created_at 2010-04-08 22:05:00
updated_at 2013-08-28 07:38:40
moldb_smiles CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12)C(O)=O
moldb_formula C30H48O3
moldb_average_mass 456.7003
moldb_inchi 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)
moldb_mono_mass 456.360345402
moldb_inchikey InChIKey=QGJZLNKBHJESQX-UHFFFAOYSA-N
moldb_iupac 17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid
Structure Thumb
Synonyms
Synonym Source
3-Hydroxylup-20(29)-en-28-oic acid biospider
3beta-Hydroxy-20(29)-lupaene-28-oic acid biospider
Betulic acid biospider
Lup-20(29)-en-28-oic acid, 3β-hydroxy- biospider
Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)- biospider
Lup-20(29)-en-28-oic acid, 3beta-hydroxy- biospider
Mairin biospider