This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Lupeol
DrugBank Accession Number
DB12622
Background

Lupeol has been investigated for the treatment of Acne.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 426.729
Monoisotopic: 426.38616623
Chemical Formula
C30H50O
Synonyms
Not Available
External IDs
  • NSC-90487

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeutrophil elastase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Triterpenoids
Direct Parent
Triterpenoids
Alternative Parents
Steroids and steroid derivatives / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Steroid / Triterpenoid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
secondary alcohol, pentacyclic triterpenoid (CHEBI:6570) / Baccharane triterpenoids, Lupanes (C08628) / Baccharane triterpenoids (LMPR0106130001)
Affected organisms
Not Available

Chemical Identifiers

UNII
O268W13H3O
CAS number
545-47-1
InChI Key
MQYXUWHLBZFQQO-QGTGJCAVSA-N
InChI
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
IUPAC Name
(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
SMILES
[H][C@]12[C@@H](CC[C@]1(C)CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(C)=C

References

General References
Not Available
KEGG Compound
C08628
PubChem Compound
259846
PubChem Substance
347828834
ChemSpider
228079
BindingDB
50377927
ChEBI
6570
ChEMBL
CHEMBL289191
ZINC
ZINC000004081455
Wikipedia
Lupeol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentAcne2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000195 mg/mLALOGPS
logP5.97ALOGPS
logP7.45Chemaxon
logS-6.3ALOGPS
pKa (Strongest Acidic)19.49Chemaxon
pKa (Strongest Basic)-0.84Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area20.23 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity130.91 m3·mol-1Chemaxon
Polarizability53.79 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serine-type endopeptidase activity
Specific Function
Modifies the functions of natural killer cells, monocytes and granulocytes. Inhibits C5a-dependent neutrophil enzyme release and chemotaxis.
Gene Name
ELANE
Uniprot ID
P08246
Uniprot Name
Neutrophil elastase
Molecular Weight
28517.81 Da
References
  1. Mitaine-Offer AC, Hornebeck W, Sauvain M, Zeches-Hanrot M: Triterpenes and phytosterols as human leucocyte elastase inhibitors. Planta Med. 2002 Oct;68(10):930-2. doi: 10.1055/s-2002-34929. [Article]

Drug created at October 20, 2016 23:16 / Updated at June 27, 2022 17:27