1.0 2010-04-08 22:05:00 UTC 2019-11-26 02:56:34 UTC FDB001532 Betulinic acid 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. 3-Hydroxy-(3beta)-lup-20(29)-en-28-Oic acid 3-Hydroxylup-20(29)-en-28-oic acid 3beta-Hydroxy-20(29)-lupaene-28-oic acid 3beta-Hydroxy-lup-20(29)-en-28-Oic acid Betulic acid Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)- Lup-20(29)-en-28-oic acid, 3&beta;-hydroxy- Lup-20(29)-en-28-oic acid, 3beta-hydroxy- Mairin C30H48O3 456.7003 456.360345402 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 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 472-15-1 CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12)C(O)=O 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) QGJZLNKBHJESQX-UHFFFAOYSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Triterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic homopolycyclic compounds 18-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxosteroids Secondary alcohols 18-hydroxysteroid 18-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Steroid Triterpenoid logp 5.34 ALOGPS logs -6.35 ALOGPS solubility 2.04e-04 g/l ALOGPS melting_point 316-318 °C logp 6.64 ChemAxon pka_strongest_acidic 4.75 ChemAxon pka_strongest_basic -0.84 ChemAxon 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 ChemAxon average_mass 456.7003 ChemAxon mono_mass 456.360345402 ChemAxon smiles CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12)C(O)=O ChemAxon formula C30H48O3 ChemAxon 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) ChemAxon inchikey QGJZLNKBHJESQX-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 132.63 ChemAxon polarizability 54.21 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15456 Specdb::CMs 41743 Specdb::CMs 123172 Specdb::CMs 817337 Specdb::CMs 817338 Specdb::CMs 817339 Specdb::CMs 817340 Specdb::CMs 817341 Specdb::MsMs 11750 Specdb::MsMs 11751 Specdb::MsMs 11752 Specdb::MsMs 18422 Specdb::MsMs 18423 Specdb::MsMs 18424 Specdb::MsMs 3403099 Specdb::MsMs 3403100 Specdb::MsMs 3403101 Specdb::MsMs 3403102 Specdb::MsMs 3403103 Specdb::MsMs 3403104 HMDB30094 #<Reference:0x000056127309c0f0> #<Reference:0x000056127309bab0> #<Reference:0x000056127309ae58> #<Reference:0x000056127309a020> #<Reference:0x0000561273099468> #<Reference:0x0000561273098dd8> Abiyuch Type 1 specific Crateva religiosa 202634 Apple Type 1 specific Malus pumila 283210 Black elderberry Type 1 specific Sambucus nigra 4202 Chicory Type 1 specific Cichorium intybus 13427 Common grape Type 1 specific Vitis vinifera 29760 Common persimmon Type 1 specific Diospyros virginiana 13493 Common walnut Type 1 specific Juglans regia 51240 4.0 4.0 4.0 mg/100 g Jackfruit Type 1 specific Artocarpus heterophyllus 3489 Japanese persimmon Type 1 specific Diospyros kaki 35925 Java plum Type 1 specific Syzygium cumini 260142 140.0 170.0 110.0 mg/100 g Jujube Type 1 specific Ziziphus zizyphus 48393 Nance Type 1 specific Byrsonima crassifolia 4270 0.34 0.34 0.34 mg/100 g Olive Type 1 specific Olea europaea 4146 Pomegranate Type 1 specific Punica granatum 22663 175.0 200.0 150.0 mg/100 g Rosemary Type 1 specific Rosmarinus officinalis 39367 Sweet basil Type 1 specific Ocimum basilicum 39350 Winged bean Type 1 specific Psophocarpus tetragonolobus 3891 5300.0 5300.0 5300.0 mg/100 g anti bacterial 145 A substance that kills or slows the growth of bacteria. anti cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. anti carcinomic 162 A substance that inhibits or prevents the proliferation of neoplasms. anti edemic 248 anti helmintic 72 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. anti HIV 333 A substance that destroys or inhibits replication of viruses. anti inflammatory 370 A substance that reduces or suppresses inflammation. anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. anti malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. anti melanomic 425 A substance that inhibits or prevents the proliferation of neoplasms. anti nociceptive 484 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. anti plasmodial 532 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. anti viral 689 A substance that destroys or inhibits replication of viruses. antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. apoptotic 704 cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. phospholipase-A2 inhibitor 1216 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4). prostaglandin synthesis inhibitor 1258 A substance that diminishes the rate of a chemical reaction.