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

Structure Search

SMILES

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

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

Molecular Formula	C30H50O
Molecular Weight	426.7174
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784308
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23196020 | https://www.ncbi.nlm.nih.gov/pubmed/15635183 | https://www.ncbi.nlm.nih.gov/pubmed/15770539

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-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784308	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784308 https://www.ncbi.nlm.nih.gov/pubmed/23196020	Primary		Basic research	Unknown Approved Use Unknown

PubMed

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
In vitro antiprotozoal activity of triterpenoid constituents of Kleinia odora growing in Saudi Arabia.	2013 Jul 31	23912274

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 03:31:13 GMT 2023` Edited by `admin` on `Sat Dec 16 03:31:13 GMT 2023`
Record UNII	E8SUT3IMRZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EPILUPEOL

Common 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

3-EPI-LUPEOL

Common Name

English

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

Common Name

English

Code System Code Type Description

CAS

4439-99-0

Created by admin on Sat Dec 16 03:31:13 GMT 2023 , Edited by admin on Sat Dec 16 03:31:13 GMT 2023

PRIMARY

PUBCHEM

5270628

Created by admin on Sat Dec 16 03:31:13 GMT 2023 , Edited by admin on Sat Dec 16 03:31:13 GMT 2023

PRIMARY

EPA CompTox

DTXSID701318679

Created by admin on Sat Dec 16 03:31:13 GMT 2023 , Edited by admin on Sat Dec 16 03:31:13 GMT 2023

PRIMARY

FDA UNII

E8SUT3IMRZ

Created by admin on Sat Dec 16 03:31:13 GMT 2023 , Edited by admin on Sat Dec 16 03:31:13 GMT 2023

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27784308Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23196020 | https://www.ncbi.nlm.nih.gov/pubmed/15635183 | https://www.ncbi.nlm.nih.gov/pubmed/15770539

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784308
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23196020 | https://www.ncbi.nlm.nih.gov/pubmed/15635183 | https://www.ncbi.nlm.nih.gov/pubmed/15770539