Record Information
Version1.0
Creation date2010-04-08 22:10:55 UTC
Update date2020-09-17 15:38:52 UTC
Primary IDFDB013802
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLanosterol
DescriptionLanosterin, also known as botalan base 138 or lanosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, lanosterin is considered to be a sterol lipid molecule. Lanosterin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number79-63-0
Structure
Thumb
Synonyms
SynonymSource
(3beta)-Lanosta-8,24-dien-3-olChEBI
(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-olChEBI
4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b)-Lanosta-8,24-dien-3-olGenerator
(3β)-Lanosta-8,24-dien-3-olGenerator
(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-olGenerator
4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-olGenerator
4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-olGenerator
(3 beta)-Lanosta-8,24-dien-3-olHMDB
(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-olHMDB
Botalan base 138HMDB
Lanosta-8,24-dien-3-olHMDB
Lanosta-8,24-dien-3beta-olHMDB
Lanosta-8,24-dienolHMDB
LanosterolHMDB
LansterHMDB
4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-olMeSH, HMDB
KryptosterolMeSH, HMDB
LanosterinChEBI
3beta-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3beta-Hydroxylanosta-8,24-dieneHMDB
3β-Hydroxy-lansota-8,24-dien-21-oic acidHMDB
3β-Hydroxylanosta-8,24-dieneHMDB
4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-olHMDB
4,4,14α-Trimethylcholesta-8,24-dien-3β-olHMDB
5alpha-Lanosta-8,24-dien-3beta-olHMDB
5α-Lanosta-8,24-dien-3β-olHMDB
Lanosta-8,24-dien-3β-olHMDB
Lanostadien-3beta-olHMDB
Lanostadien-3β-olHMDB
(3beta,5alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-olbiospider
(3β,5α)-4,4,14-trimethylcholesta-8,24-dien-3-olGenerator
(3β)-lanosta-8,24-dien-3-olGenerator
3beta-Hydroxy-8,24-lanostadienebiospider
4,4',14α-trimethyl-5α-cholesta-8,24-dien-3β-olGenerator
8,24-Lanostadien-3beta-olbiospider
Cryptosteroldb_source
Isocholesteroldb_source
Lanosta-8,24-dien-3-ol, (3β)-biospider
Lanosta-8,24-dien-3β-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity134.54 m³·mol⁻¹ChemAxon
Polarizability55.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O
IUPAC name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
InChI IdentifierInChI=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
InChI KeyCAHGCLMLTWQZNJ-BQNIITSRSA-N
Isomeric 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
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
Classification
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.44%; H 11.81%; O 3.75%DFC
Melting PointMp 140-141°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical Rotation[a]17D +58 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-2953300000-ae1832f19369485ff53cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0aou-9820200000-573525b346ad3c9eef59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4l-2910000000-c67a1f122f33698a14f6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0a6r-0110900000-5e42e1f2d9ad534c003cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0a4i-0230900000-10f58fa6e118cd7c5997JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-1791800000-178153ad92eececb33c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0a4i-2980300000-6ce95c7f8b15b35475afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-0a4j-2950100000-48f86ff7a22c596aa44dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0592-3940000000-c35d0cb6a2e4e291e8f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0592-3920000000-d717fdd3322a881bef99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-0592-4910000000-4c6d07e3a8e48ae88580JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0a4j-5900000000-4c8b72037dbeae9a46d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-067m-8900000000-522b8688d50362297c41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 62V, positivesplash10-0aou-9700000000-70d433827c1a6dab0c41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-05ox-9500000000-5b122dea636d3e3b5916JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 90V, positivesplash10-05r3-9500000000-0c1c5cbd994f8406f30eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 111V, positivesplash10-05r3-9600000000-5cb8ae11d071fa19f206JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0ktf-0392000000-03cda521ce6e102d92e4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-059j-2900000000-8086693fb040e5ed7501JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0a4i-4900000000-c58ff2dc28c6ba639997JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-01vk-0900000000-805937445cceda0cd70aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0aor-0900000000-22d304b445b737121aa7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-2cfcf7ce4b5b21140eaeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-2139500000-9a25961000db9796d6daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4259100000-9f7f26265abec4122e35JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-77a57cecc2069bee1926JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-5b0f06bf8120e780e30cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-421e305d47b29da427d2JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd687JSpectraViewer | MoNA
ChemSpider ID216175
ChEMBL IDCHEMBL225111
KEGG Compound IDC01724
Pubchem Compound ID246983
Pubchem Substance IDNot Available
ChEBI ID16521
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01251
CRC / DFC (Dictionary of Food Compounds) IDJHN22-K:JHN22-K
EAFUS IDNot Available
Dr. Duke IDLANOSTEROL
BIGG ID38253
KNApSAcK IDC00003657
HET IDLAN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLanosterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Enzymes
NameGene NameUniProt ID
Lanosterol synthaseLSSP48449
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.