Celastrol
PubChem CID: 122724
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| Compound 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, NSC 70931, UNII-L8GG98663L, CHEBI:63959, L8GG98663L, CELASTROL [MI], NSC70931, MFCD03424073, NSC-70931, DTXSID2040993, 34157-83-0 (castrol), 3-hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid, compound 2 [PMID: 28621943], Celastrol (>85%), D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-, Celastrol, Celastrus scandens, C29H38O4, compound 2 (PMID: 28621943), (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-, (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, 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, SR-05000002679, MLS002701906, 3-Hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-oic Acid, Celastrol?, Celastrol (Standard), Spectrum_000335, Pristimerin (Celastrol), Spectrum2_000150, Spectrum3_000233, Spectrum4_001966, Spectrum5_000805, SCHEMBL14954, BSPBio_001905, KBioGR_002436, KBioSS_000815, SPECTRUM201664, MLS006011086, DivK1c_000718, SPBio_000260, DTXCID0020993, GTPL10386, KBio1_000718, KBio2_000815, KBio2_003383, KBio2_005951, KBio3_001405, NINDS_000718, BDBM205457, GLXC-02518, HMS1923A13, HMS3649E12, HMS3884G09, BCP07973, EX-A7823, CCG-39919, HB4605, HY-13067R, s1290, Celastrol, >=98% (HPLC), solid, AKOS025311497, AC-6031, CS-0409, FC19885, GS-6082, IDI1_000718, NCGC00178913-01, NCGC00178913-02, NCGC00178913-04, NCGC00178913-05, NCGC00178913-14, HY-13067, NCI60_038570, SMR004702874, 1ST157285, C2737, H10498, AK-693/21141017, Q5057534, SR-05000002679-1, SR-05000002679-3, SR-05000002679-4, 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-9I2,13I+--dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate, (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-picenecarboxylate, 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-tetradecahydro-picene-2-carboxylic 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-, (9BETA,13ALPHA,14BETA,20ALPHA)-, 3-Hydroxy-2-oxo-24-nor-D:A-friedooleana-1(10),3,5,7-tetraen-29-oic acid, Tripterin, (9b,13a,14b,20a)-3-Hydroxy-9,13-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-9I2,13I+--dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 74.6 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CCC2CCC3C(CCC4C5CCCCC5CCC43)C2C1 |
| Deep Smiles | O=CC=CC=CC=C[C@@]6C)CC[C@@][C@]6C)CC[C@@][C@H]6C[C@@]C)CC6))C=O)O)))))C)))))C))))))))C=C6O))C |
| Heavy Atom Count | 33.0 |
| Classyfire Class | Prenol lipids |
| Description | 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] |
| Scaffold Graph Node Level | OC1CCC2CCC3C(CCC4C5CCCCC5CCC43)C2C1 |
| Classyfire Subclass | Triterpenoids |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 1100.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 6.0 |
| Uniprot Id | n.a., Q00613, P0C6X7, Q06124, P29350, P18031, P35236, O42275, P81908, Q9Y6L6, Q9NPD5, O14746, P08238, Q9UGC6, E9QYP0, P60484, Q12913, P23469, P17706, Q7BGE6, P22736 |
| Iupac Name | (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 |
| Prediction Hob | 0.0 |
| Class | Prenol lipids |
| Veber Rule | True |
| Classyfire Superclass | Lipids and lipid-like molecules |
| Target Id | NPT1583, NPT206, NPT205, NPT178, NPT2570, NPT144, NPT1210 |
| Xlogp | 5.9 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Triterpenoids |
| Gsk 4 400 Rule | False |
| Molecular Formula | C29H38O4 |
| Scaffold Graph Node Bond Level | O=C1C=CC2=CC=C3C(CCC4C3CCC3CCCCC34)C2=C1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | KQJSQWZMSAGSHN-JJWQIEBTSA-N |
| Silicos It Class | Moderately soluble |
| Fcsp3 | 0.6551724137931034 |
| Logs | -3.468 |
| Rotatable Bond Count | 1.0 |
| State | Solid |
| Logd | 3.34 |
| Synonyms | (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, (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, (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, 3-Hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-Oic acid, Tripterin, (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, 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, celastrol, triterpene |
| Substituent Name | Polycyclic triterpenoid, Triterpenoid, Cyclic ketone, Ketone, Monocarboxylic acid or derivatives, Enol, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aliphatic homopolycyclic compound |
| Esol Class | Poorly soluble |
| Functional Groups | CC(=O)O, CC1=C(O)C(=O)C=C2CC(C)=CC=C21 |
| Compound Name | Celastrol |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 450.277 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 450.277 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 450.6 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -6.310037800000003 |
| 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 |
| Smiles | CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C)O |
| Nring | 5.0 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Triterpenoids |
| Np Classifier Superclass | Triterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Angelica Keiskei (Plant) Rel Props:Source_db:npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Barringtonia Acutangula (Plant) Rel Props:Reference:ISBN:9770972795006 - 3. Outgoing r'ship
FOUND_INto/from Berberis Lambertii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Celastrus Orbiculatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Celastrus Paniculatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Centella Asiatica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
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FOUND_INto/from Dipterocarpus Costatus (Plant) Rel Props:Reference:ISBN:9788172363178 - 9. Outgoing r'ship
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FOUND_INto/from Litsea Gracilipes (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 18. Outgoing r'ship
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FOUND_INto/from Polyalthia Longifolia (Plant) Rel Props:Reference:ISBN:9780387706375 - 20. Outgoing r'ship
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FOUND_INto/from Taraxacum Officinale (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 25. Outgoing r'ship
FOUND_INto/from Taraxacum Platycarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 26. Outgoing r'ship
FOUND_INto/from Terminalia Bellirica (Plant) Rel Props:Reference:ISBN:9788172363093 - 27. Outgoing r'ship
FOUND_INto/from Terminalia Chebula (Plant) Rel Props:Reference:ISBN:9788172363093 - 28. Outgoing r'ship
FOUND_INto/from Thunbergia Grandiflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 29. Outgoing r'ship
FOUND_INto/from Triadica Sebifera (Plant) Rel Props:Reference:ISBN:9780387706375 - 30. Outgoing r'ship
FOUND_INto/from Trichosanthes Kirilowii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 31. Outgoing r'ship
FOUND_INto/from Tripterygium Wilfordii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 32. Outgoing r'ship
FOUND_INto/from Vitex Negundo (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/27118321 - 33. Outgoing r'ship
FOUND_INto/from Zanthoxylum Syncarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all