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Lanosterol

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Identification

Generic Name
Lanosterol
DrugBank Accession Number
DB03696
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 426.7174
Monoisotopic: 426.386166222
Chemical Formula
C30H50O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULanosterol synthaseNot AvailableHumans
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
3-beta-hydroxysteroids / 14-alpha-methylsteroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
14-alpha-methylsteroid / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-sterol, tetracyclic triterpenoid (CHEBI:16521) / Cholesterol and derivatives (C01724) / Cholesterol and derivatives (LMST01010017)
Affected organisms
Not Available

Chemical Identifiers

UNII
1J05Z83K3M
CAS number
79-63-0
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
(1R,3aR,5aR,7S,9aS,11aR)-3a,6,6,9a,11a-pentamethyl-1-[(2R)-6-methylhept-5-en-2-yl]-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9H,9aH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
SMILES
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

References

General References
Not Available
Human Metabolome Database
HMDB0001251
KEGG Compound
C01724
PubChem Compound
246983
PubChem Substance
46506323
ChemSpider
216175
RxNav
1442199
ChEBI
16521
ChEMBL
CHEMBL225111
ZINC
ZINC000003870056
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
LAN
Wikipedia
Lanosterol
PDB Entries
1w6k / 4lxj / 6uez / 7snm

Clinical Trials

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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
Polarizability55.06 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-MSsplash10-03dj-1009400000-e2b516142f5128a7b5f6
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/MSsplash10-054k-9001100000-125c15e67f3a65741f65
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-baa276e1b54ab0ff5f63
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-9012000000-78b49aed79c40a9b38d7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0003900000-96811f70942032ff8bfb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-1007900000-83c1dcb786448299e803
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-9124000000-82a5b199bceb70b760ca
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-224.3788341
predicted
DarkChem Lite v0.1.0
[M-H]-223.1709341
predicted
DarkChem Lite v0.1.0
[M-H]-221.9293341
predicted
DarkChem Lite v0.1.0
[M-H]-231.2178341
predicted
DarkChem Lite v0.1.0
[M-H]-215.27534
predicted
DeepCCS 1.0 (2019)
[M+H]+225.0934341
predicted
DarkChem Lite v0.1.0
[M+H]+223.3778341
predicted
DarkChem Lite v0.1.0
[M+H]+222.4443341
predicted
DarkChem Lite v0.1.0
[M+H]+231.7517341
predicted
DarkChem Lite v0.1.0
[M+H]+217.17073
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.5424341
predicted
DarkChem Lite v0.1.0
[M+Na]+223.4013341
predicted
DarkChem Lite v0.1.0
[M+Na]+222.0443341
predicted
DarkChem Lite v0.1.0
[M+Na]+231.2883341
predicted
DarkChem Lite v0.1.0
[M+Na]+222.94875
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lanosterol synthase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Key enzyme in the cholesterol biosynthesis pathway. Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus (PubMed:14766201, PubMed:26200341, PubMed:7639730). Through the production of lanosterol may regulate lens protein aggregation and increase transparency (PubMed:26200341)
Specific Function
lanosterol synthase activity
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52