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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

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

Molecular Formula C30H50O
Molecular Weight 426.7174
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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
Record UNII
E8SUT3IMRZ
Record Status Validated (UNII)
Record Version