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Identification
NameLanosterol
Accession NumberDB03696  (EXPT02002)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1J05Z83K3M
CAS number79-63-0
WeightAverage: 426.7174
Monoisotopic: 426.386166222
Chemical FormulaC30H50O
InChI KeyInChIKey=CAHGCLMLTWQZNJ-RGEKOYMOSA-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+/m0/s1
IUPAC Name
(2R,5R,7S,11S,14S,15R)-2,6,6,11,15-pentamethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
SMILES
C[C@@H](CCC=C(C)C)[C@@H]1CC[C@]2(C)C3=C(CC[C@]12C)[C@]1(C)CC[C@@H](O)C(C)(C)[[email protected]]1CC3
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tirucallane and euphane triterpenoids. These are triterpenoids with a structure based either on the tirucallane or the euphane skeleton. They are obtained by backbone rearrangement of a dammarane-based precursor.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTirucallane and euphane triterpenoids
Alternative Parents
Substituents
  • Tirucallane-euphane triterpenoid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point140.5 °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
Polarizability55.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23