Lanosterol

Identification

Name
Lanosterol
Accession Number
DB03696  (EXPT02002)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
1J05Z83K3M
CAS number
79-63-0
Weight
Average: 426.7174
Monoisotopic: 426.386166222
Chemical Formula
C30H50O
InChI Key
CAHGCLMLTWQZNJ-BQNIITSRSA-N
InChI
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
IUPAC Name
(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULanosterol synthaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01251
KEGG Compound
C01724
PubChem Compound
246983
PubChem Substance
46506323
ChemSpider
216175
ChEBI
16521
ChEMBL
CHEMBL225111
IUPHAR
2746
Guide to Pharmacology
GtP Drug Page
HET
LAN
PDB Entries
1w6k / 4lxj

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000376 mg/mLALOGPS
logP7.72ALOGPS
logP7.71ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.54 m3·mol-1ChemAxon
Polarizability54.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9825
Caco-2 permeable+0.8378
P-glycoprotein substrateSubstrate0.6817
P-glycoprotein inhibitor IInhibitor0.5585
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.7423
CYP450 2C9 substrateNon-substrate0.7988
CYP450 2D6 substrateNon-substrate0.8856
CYP450 3A4 substrateSubstrate0.7771
CYP450 1A2 substrateNon-inhibitor0.9088
CYP450 2C9 inhibitorNon-inhibitor0.8612
CYP450 2D6 inhibitorNon-inhibitor0.9483
CYP450 2C19 inhibitorNon-inhibitor0.7681
CYP450 3A4 inhibitorNon-inhibitor0.864
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5784
Ames testNon AMES toxic0.8954
CarcinogenicityNon-carcinogens0.9335
BiodegradationNot ready biodegradable0.9861
Rat acute toxicity2.5576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7863
hERG inhibition (predictor II)Non-inhibitor0.7617
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0a4l-4910000000-0fe7f84c95ab0a849fe9
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03dl-2953300000-ae1832f19369485ff53c
GC-MS Spectrum - EI-BGC-MSsplash10-0aou-9820200000-573525b346ad3c9eef59
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4l-4910000000-0fe7f84c95ab0a849fe9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4l-2910000000-c67a1f122f33698a14f6
Mass Spectrum (Electron Ionization)MSsplash10-05mo-9731200000-b1bc6bb68e352e3bd687
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

Taxonomy

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
3-beta-hydroxysteroids / 14-alpha-methylsteroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Triterpenoid / 14-alpha-methylsteroid / 3-beta-hydroxysteroid / Hydroxysteroid / 3-hydroxysteroid / Steroid / Cyclic alcohol / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-sterol, tetracyclic triterpenoid (CHEBI:16521) / Cholesterol and derivatives (C01724) / Cholesterol and derivatives (LMST01010017)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Lanosterol synthase activity
Specific Function
Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
Gene Name
LSS
Uniprot ID
P48449
Uniprot Name
Lanosterol synthase
Molecular Weight
83308.065 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:31