EPILUPEOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H50O
Molecular Weight	426.7174
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(=C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12

InChI

InChIKey=MQYXUWHLBZFQQO-ISZJTHHZSA-N

InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24+,25+,27+,28-,29+,30+/m0/s1

HIDE SMILES / InChI

Description

Epilupeol is a plant-derived lupane-type 3α-hydroxy triterpenoid. Epilupeol has been little studied, although its anti-inflammatory, antitubercular, and cytotoxic activities have been described.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 105	Primary		Basic research	Unknown

PubMed

Show entries

Title	Date	PubMed
Antitubercular activity of triterpenoids from Asteraceae flowers.	2005 Jan	15635183
Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis.	2005 Mar	15770539
Chemical and biological investigations of Delonix regia (Bojer ex Hook.) Raf.	2010 Jun	21134857
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.	2012 Apr 27	22462772
In vitro antiprotozoal activity of triterpenoid constituents of Kleinia odora growing in Saudi Arabia.	2013 Jul 31	23912274

Showing 1 to 5 of 6 entries

Previous1 2Next

Patents

Sample Use Guides

In Vivo Use Guide

Application of 3-epilupeol (2, 1, 0.5, 0.2 or 0.1 mg/ ear; ID50 - 0.4 mg) inhibited in a dose-dependent manner the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (TPA-induced auricular edema in mouse model)

Route of Administration: Otic (auricular)

In Vitro Use Guide

Minimum inhibitory concentration against Mycobacterium tuberculosis strain H37Rv for 3-epilupeol was 4 ug/ml. Cytotoxicity of 3-epilupeol against Vero cells gave an IC50 value of over 62.5 μg/ml, suggesting some degree of selectivity for M. tuberculosis.

Show entries

Name

Type

Language

EPILUPEOL

Common Name

English

3-EPI-LUPEOL

Preferred Name

English

LUP-20(30)-EN-3.ALPHA.-OL

Common Name

English

LUP-20(29)-EN-3.ALPHA.-OL

Common Name

English

3-EPILUPEOL

Common Name

English

Showing 1 to 5 of 6 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

CAS

4439-99-0

PRIMARY

PUBCHEM

5270628

PRIMARY

EPA CompTox

DTXSID701318679

PRIMARY

FDA UNII

E8SUT3IMRZ

PRIMARY

Showing 1 to 4 of 4 entries

Previous1Next

SUBSTANCE RECORD


					E8SUT3IMRZ

EPILUPEOL