CELASTROL METHYL ESTER

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H40O4
Molecular Weight	464.6362
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

InChI

InChIKey=JFACETXYABVHFD-WXPPGMDDSA-N

InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C30H40O4
Molecular Weight	464.6362
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19096011
Curator's Comment: description was created based on several sources, including https://www.nature.com/nature/journal/v173/n4417/abs/1731237b0.html | https://www.ncbi.nlm.nih.gov/pubmed/25308129

Pristimerin, the methyl ester of celasterol, is a triterpenoid quinone methide isolated from Pristimerae indica. Pristimerin shows anticancer activity in vitro towards myeloma, prostate, breast, ovarian cancer cell lines and inhibits xenografted plasmacytoma tumors in mice. In a rat model of adjuvant arthritis, pristimerin effectively inhibited both arthritic inflammation and cartilage and bone damage in the joints. Pristimerin acts by inhibiting NF-kB signaling pathway and the 26S proteasome.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
26S proteosome 7 Target ID: CHEMBL2364701 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17541980	Inhibitor 8504	3.0 µM [IC50]
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19096011	Inhibitor 8504
Vascular endothelial growth factor receptor 2 112 Target ID: P35968 Gene ID: 3791.0 Gene Symbol: KDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22669041	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17541980 https://www.ncbi.nlm.nih.gov/pubmed/16093444 https://www.ncbi.nlm.nih.gov/pubmed/19096011	Primary		Preclinical	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25308129	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pristimerin, a naturally occurring triterpenoid, protects against autoimmune arthritis by modulating the cellular and soluble immune mediators of inflammation and tissue damage.	2014-12	25308129
Pristimerin, a triterpenoid, inhibits tumor angiogenesis by targeting VEGFR2 activation.	2012-06-05	22669041
Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo.	2009-04-23	19096011
Pristimerin induces apoptosis by targeting the proteasome in prostate cancer cells.	2008-01-01	17541980

Patents

Sample Use Guides

In Vivo Use Guide

In a study of human myeloma xenograft tumors in nude mice, a liposomal formulation of the pristimerin was developed, successfully incorporating 98.7% of the drug and given by intravenous tail vein injection. Statistically significant tumor growth inhibition occurred at pristimerin doses of 2 to 3 mg/kg intravenously twice weekly.

Route of Administration: Intravenous

In Vitro Use Guide

Cytotoxicity of pristimerin towards human myeloma cell lines U266, H929, KMS18, OPM1 was assessed by MTT assay at 72 hours. The median IC50 of pristimerin against myeloma cell lines is approximately 200 nM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:35:03 GMT 2025` Edited by `admin` on `Mon Mar 31 23:35:03 GMT 2025`
Record UNII	28ZK7PR57S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CELASTROL METHYL ESTER

Common Name

English

PRISTIMERIN

Preferred Name

English

24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-9,13-DIMETHYL-2-OXO-, METHYL ESTER, (9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-

Systematic Name

English

NSC-99281

Code

English

(9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-3-HYDROXY-9,13-DIMETHYL-2-OXO-24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID

Systematic Name

English

CELASTROL METHYL ESTER [MI]

Common Name

English

Code System Code Type Description

CAS

1258-84-0