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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

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antitubercular activity of triterpenoids from Asteraceae flowers.
2005 Jan
Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis.
2005 Mar
Chemical and biological investigations of Delonix regia (Bojer ex Hook.) Raf.
2010 Jun
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
2012 Apr 27
In vitro antiprotozoal activity of triterpenoid constituents of Kleinia odora growing in Saudi Arabia.
2013 Jul 31
Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera.
2016 Oct 26
Patents

Sample Use Guides

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)
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
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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
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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