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Chemical Entities of Biological Interest Ontology

Last uploaded: January 1, 2025
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Id http://purl.obolibrary.org/obo/CHEBI_63959
http://purl.obolibrary.org/obo/CHEBI_63959
Preferred Name

celastrol
Definitions
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 NFkappaB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 muM).
Synonyms
Tripterine
D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-
3-hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-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-picenecarboxylic acid
(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
Type http://www.w3.org/2002/07/owl#Class

All Properties

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-alpha-induced NFkappaB activation. Also shown to inhibit topoisomerase II activity in vitro (IC50 = 7.41 muM).
label
celastrol
prefLabel
celastrol
database_cross_reference
HMDB:HMDB0002385
PMID:21850367
CAS:34157-83-0
Patent:KR20100097843
PMID:21425580
PMID:15593077
PMID:20954803
PMID:20934245
Patent:US2011263693
PMID:21666907
PMID:21865725
PMID:21134410
Reaxys:2194425
PMID:21866552
PMID:11809076
PMID:21569548
PMID:21466843
PMID:22334592
PMID:22206928
PMID:22087583
PMID:21414301
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notation
CHEBI:63959
in_subset
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
has_related_synonym
Tripterine
D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-
3-hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-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-picenecarboxylic acid
id
CHEBI:63959
charge
0
has_obo_namespace
chebi_ontology
formula
C29H38O4
subClassOf
inchikey
KQJSQWZMSAGSHN-JJWQIEBTSA-N
mass
450.60960
monoisotopicmass
450.27701
type
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
has role
has_exact_synonym
(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
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