Compound: celastrol
SMILES: O=C1C(O)=C(C2=CC=C3[C@](C2=C1)(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@@](C(=O)O)(C)CC5)C)C)C)C)C
InChIKey: KQJSQWZMSAGSHN-JJWQIEBTSA-N
Synonyms: celastrol, 34157-83-0, Tripterin, Tripterine, (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, (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid, L8GG98663L, NSC-70931, DTXSID2040993, CHEBI:63959, D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-, 3-Hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-oic Acid, RefChem:124284, DTXCID0020993, MFCD03424073, NSC70931, Celastrol (>85%), 3-hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid, Celastrol, Celastrus scandens, SR-05000002679, MLS002701906, NSC 70931, UNII-L8GG98663L, Celastrol?, 34157-83-0 (castrol), Celastrol,Tripterin, Celastrol (Standard), Spectrum_000335, Pristimerin (Celastrol), CELASTROL [MI], Spectrum2_000150, Spectrum3_000233, Spectrum4_001966, Spectrum5_000805, SCHEMBL14954, BSPBio_001905, KBioGR_002436, KBioSS_000815, SPECTRUM201664, MLS006011086, DivK1c_000718, SPBio_000260, orb1304608, orb3140252, GTPL10386, KBio1_000718, KBio2_000815, KBio2_003383, KBio2_005951, KBio3_001405, NINDS_000718, BDBM205457, GLXC-02518, HMS1923A13, HMS3649E12, HMS3884G09, HMS6019F07, EX-A7823, CCG-39919, EBC-11155, HB4605, HY-13067R, MSK157285, s1290, Celastrol, >=98% (HPLC), solid, AKOS025311497, AC-6031, compound 2 [PMID: 28621943], CS-0409, FC19885, GS-6082, IDI1_000718, NCGC00178913-01, NCGC00178913-02, NCGC00178913-04, NCGC00178913-05, NCGC00178913-14, NCGC00178913-15, HY-13067, NCI60_038570, SMR004702874, SY028490, C2737, H10498, AK-693/21141017, Q5057534, SR-05000002679-1, SR-05000002679-3, SR-05000002679-4, (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, 24-NOR-D:A-FRIEDOOLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-2-OXO-, 3-Hydroxy-2-oxo-24-nor-D:A-friedooleana-1(10),3,5,7-tetraen-29-oic acid, (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylicacid, (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, (9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24, 25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic 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, 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-, (2R,4aS,6aS,12bR,14aS,14bR)-, 2-Picenecarboxylic acid,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-, 24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-9,13-DIMETHYL-2-OXO-, (9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-, 3-Hydroxy-9.beta.,13.alpha.-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
Theoretical properties:
molecular_formula: C29H38O4
molecular_weight: 450.6 g/mol
exact_mass: 450.27700969 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 33
topological_polar_surface_area: 74.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Celastrol is a pentacyclic triterpenoid that is 24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid bearing an oxo substituent at position 2, a hydroxy substituent at position 3 and two methyl groups at positions 9 and 13. An antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF-alpha-induced NFB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 M). It has a role as an antioxidant, a metabolite, an anti-inflammatory drug, an antineoplastic agent, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and a Hsp90 inhibitor. It is a monocarboxylic acid and a pentacyclic triterpenoid.", "chebi": "A pentacyclic triterpenoid that is 24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid bearing an oxo substituent at position 2, a hydroxy substituent at position 3 and two methyl groups at positions 9 and 13. An antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF-\u03b1-induced NF\u03baB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 \u03bcM).", "chembl": "CELASTROL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Celastrol (tripterine) is a bioactive chemical compound isolated from the roots of Tripterygium wilfordii (Thunder duke vine) and Tripterygium regelii (Regel's threewingnut). Celastrol is a pentacyclic nortriterpen quinone and belongs to the family of quinone methides. It has been used for centuries as a traditional Chinese medicine. In recent years, celastrol has been widely studied for its anti-inflammatory, anticancer, antioxidant, and antibacterial properties.\nIn mice, celastrol is an NR4A1 agonist that alleviates inflammation and induces autophagy. It also influences metabolic regulation by enhancing IL1R1 expression, which is the receptor for the cytokine interleukin-1 (IL-1). IL1R1 knock-out mice exposed to celastrol exhibit no leptin-sensitizing or anti-obesity effect.\nIn in vitro and in vivo animal experiments, celastrol exhibits antibacterial, antioxidant, anti-inflammatory, anticancer, and insecticidal properties. It has been shown to have obesity-controlling effects in mice by inhibiting negative regulators of leptin. Celastrol has also shown to possess anti-diabetic effects on diabetic nephropathy and improve whole-body insulin resistance, through the inhibition of NF-\u03baB signaling in the hypothalamus.\nCelastrol inhibits the IKK-NF-\u03baB signaling pathway via multiple molecular mechanisms, including the direct inhibition of IKK\u03b1 and IKK\u03b2 kinases, inactivation of CDC37 and p23 (HSP90 chaperone proteins), suppression of proteasome function and activation of HSF1, which triggers the heat shock response. The available evidence indicates that celastrol covalently binds to the thiol groups of cysteine residues within its molecular targets.\nCelastrol also has demonstrated in vitro inhibitory effects against the carbapenemase of carbapenem-resistant Klebsiella pneumoniae (CRE), particularly when used in combination with thymol, a monoterpene."}