Celastrol
(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
Molecular Identity
Celastrol
(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
PubChem CID: 122724
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.
2D Structure
Properties
C29H38O4
Molecular Formula
450.60
Molecular Weight
g/mol
450.2770
Exact Mass
Da
5.9
XLogP
Above Lipinski threshold
74.6
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
4
H-Bond Acceptors
1100
Complexity
SMILES
Canonical SMILES
SMILES: CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)OIsomeric SMILES
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)OSynonyms(20)
celastrol34157-83-0TripterinTripterine(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 acidCHEBI:63959L8GG98663LNSC-70931DTXSID2040993D: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 AcidRefChem:124284DTXCID0020993MFCD03424073
Data from PubChem (NCBI)
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