1.0 2011-09-21 00:22:55 UTC 2015-07-21 06:57:28 UTC FDB022989 Celastrol Celastrol, a plant-derived triterpene, has antioxidant and anti-inflammatory activity that may prevent neuronal degeneration in Alzheimer's disease (AD). In the brains of patients with AD signs of neuronal degeneration are accompanied by markers of microglial activation, inflammation, and oxidant damage. The presence of nitrotyrosine in the cell bodies of neurons in AD suggests that peroxynitrite contributes to the pathogenesis of the disease. In low nanomolar concentrations celastrol was found to suppress the production by human monocytes and macrophages of the pro-inflammatory cytokines TNF-alpha and IL-1beta. Celastrol also decreased the induced expression of class II MHC molecules by microglia. In macrophage lineage cells and endothelial cells celastrol decreased induced but not constitutive NO production. Celastrol suppresses adjuvant arthritis in the rat, demonstrating in vivo anti-inflammatory activity. Low doses of celastrol administered to rats significantly improved their performance in memory, learning and psychomotor activity tests. The potent antioxidant and anti-inflammatory activities of celastrol, and its effects on cognitive functions, suggest that the drug may be useful to treat neurodegenerative diseases accompanied by inflammation, such as AD. (PMID: 11513350) [HMDB] (20alpha)-3-hydroxy-2-oxo-D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oate (20alpha)-3-hydroxy-2-oxo-D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid (2R,4AS,6as,12br,14as,14br)-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-2-picenecarboxylate (2R,4AS,6as,12br,14as,14br)-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-2-picenecarboxylic acid 1,2,3,4,4a,5,6,6a, 11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b, 14a-hexamethyl-11-oxo-2-Picenecarboxylic acid 3-Hydroxy-9b,13a-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate 3-Hydroxy-9b,13a-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid 3-Hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate 3-Hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid 3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate 3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid celastrol Tripterine C29H38O4 450.6096 450.277009704 (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid triterpene 34157-83-0 [H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(C)=C(O)C(=O)C=C4[C@]3(C)CC[C@@]21C)C(O)=O InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1 KQJSQWZMSAGSHN-JJWQIEBTSA-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 Carboxylic acids Cyclic ketones Enols Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic ketone Enol Hydrocarbon derivative Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Triterpenoid monocarboxylic acid pentacyclic triterpenoid Solid logp 6.10 ALOGPS logs -5.29 ALOGPS solubility 2.33e-03 g/l ALOGPS logp 5.33 ChemAxon pka_strongest_acidic 4.78 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid ChemAxon average_mass 450.6096 ChemAxon mono_mass 450.277009704 ChemAxon smiles [H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(C)=C(O)C(=O)C=C4[C@]3(C)CC[C@@]21C)C(O)=O ChemAxon formula C29H38O4 ChemAxon inchi InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1 ChemAxon inchikey KQJSQWZMSAGSHN-JJWQIEBTSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 132.75 ChemAxon polarizability 51.31 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 22927 Specdb::CMs 38403 Specdb::CMs 161429 Specdb::MsMs 316915 Specdb::MsMs 316916 Specdb::MsMs 316917 Specdb::MsMs 363286 Specdb::MsMs 363287 Specdb::MsMs 363288 Specdb::MsMs 439775 Specdb::MsMs 449923 Specdb::MsMs 449924 Specdb::MsMs 449925 Specdb::MsMs 2254147 Specdb::MsMs 2254364 Specdb::MsMs 2256221 Specdb::MsMs 2425255 Specdb::MsMs 2425256 Specdb::MsMs 2425257 Specdb::MsMs 2510464 Specdb::MsMs 2510465 Specdb::MsMs 2510466 HMDB02385 #<Reference:0x000055ce32ab11b0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823