CHEBI:63959 - celastrol

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ChEBI Name celastrol
ChEBI ID CHEBI:63959
Definition 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-α-induced NFκB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 μM).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C29H38O4
Net Charge 0
Average Mass 450.60960
Monoisotopic Mass 450.277
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
InChIKey KQJSQWZMSAGSHN-JJWQIEBTSA-N
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
Metabolite of Species Details
Tripterygium wilfordii (NCBI:txid458696) Found in root (BTO:0001188). Root extract See: PubMed
Tripterygium wilfordii (NCBI:txid458696) Found in root (BTO:0001188). Previous component: root bark; See: DOI
Celastrus hypoleucus (NCBI:txid489980) Found in root (BTO:0001188). See: PubMed
Celastrus orbiculatus (NCBI:txid85181) Found in root (BTO:0001188). See: PubMed
Celastrus paniculatus (NCBI:txid994668) Found in root (BTO:0001188). Previous component: root outer bark; See: DOI
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application(s): anti-inflammatory drug
A substance that reduces or suppresses inflammation.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(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 ChEBI
3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid ChEBI
D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)- ChemIDplus
Tripterine ChemIDplus
Manual Xrefs Databases
HMDB0002385 HMDB
KR20100097843 Patent
US2011263693 Patent
View more database links
Registry Numbers Types Sources
2194425 Reaxys Registry Number Reaxys
34157-83-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11809076 PubMed citation Europe PMC
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Last Modified
10 September 2012