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CHEBI:63959 - celastrol

Default Structure
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
Celastrus hypoleucus (ncbitaxon:489980) root (BTO:0001188) PubMed (15593077)
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (11809076)
Celastrus paniculatus (ncbitaxon:994668) root (BTO:0001188) DOI (10.1016/0031-9422(90)80182-G) Previous component: root outer bark;
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
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:
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
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.
Applications:
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
(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
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
TripterineChemIDplus
Manual XrefsDatabases
HMDB0002385HMDB
KR20100097843Patent
US2011263693Patent
Registry NumbersSources
Reaxys:2194425Reaxys
CAS:34157-83-0ChemIDplus
Citations