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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 of EPILUPEOL

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

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera.
2016 Oct 26
Patents

Patents

US20140023721A1
1

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.
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
SUBSTANCE RECORD
Structure of EPILUPEOL
NIH
NCATS
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