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CHEBI:63959 - celastrol

ChEBI IDCHEBI:63959
ChEBI Namecelastrol
Stars
DefinitionA 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-α-induced NFκB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 μM).
Last Modified10 September 2012
SubmitterSteve
DownloadsMolfile
FormulaC29H38O4
Net Charge0
Average Mass450.619
Monoisotopic Mass450.27701
SMILES[H][C@@]12C[C@](C)(C(=O)O)CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(=CC(=O)C(O)=C4C)[C@]3(C)CC[C@@]21C
InChIInChI=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
InChIKeyKQJSQWZMSAGSHN-JJWQIEBTSA-N
Species of MetaboliteComponentSourceComments
Tripterygium wilfordii (ncbitaxon:458696)
root (BTO:0001188) DOI (10.1186/1471-2202-6-1) Previous component: root bark;
root (BTO:0001188) PubMed (21486005) Root extract
Celastrus paniculatus (ncbitaxon:994668) root (BTO:0001188) DOI (10.1016/0031-9422(90)80182-G) Previous component: root outer bark;
Celastrus hypoleucus (ncbitaxon:489980) root (BTO:0001188) PubMed (15593077)
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (11809076)
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
ChEBI Ontology
Outgoing Relation(s)
celastrol (CHEBI:63959) has role anti-inflammatory drug (CHEBI:35472)
celastrol (CHEBI:63959) has role antineoplastic agent (CHEBI:35610)
celastrol (CHEBI:63959) has role antioxidant (CHEBI:22586)
celastrol (CHEBI:63959) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
celastrol (CHEBI:63959) has role Hsp90 inhibitor (CHEBI:63962)
celastrol (CHEBI:63959) has role metabolite (CHEBI:25212)
celastrol (CHEBI:63959) is a monocarboxylic acid (CHEBI:25384)
celastrol (CHEBI:63959) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(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
Synonyms  Source
TripterineChemIDplus
3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acidChEBI
D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-ChemIDplus
(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 acidChEBI
Manual XrefsDatabases
US2011263693Patent
KR20100097843Patent
HMDB0002385HMDB
Registry NumbersSources
Reaxys:2194425Reaxys
CAS:34157-83-0ChemIDplus
Citations