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Lanosterol (FDB013802)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-05mo-9731200000-b1bc6bb68e352e3bd6872015-03-01View Spectrum
GC-MSLanosterol, 1 TMS, GC-MS Spectrumsplash10-0a4l-4910000000-0fe7f84c95ab0a849fe9Spectrum
GC-MSLanosterol, non-derivatized, GC-MS Spectrumsplash10-03dl-2953300000-ae1832f19369485ff53cSpectrum
GC-MSLanosterol, non-derivatized, GC-MS Spectrumsplash10-0aou-9820200000-573525b346ad3c9eef59Spectrum
GC-MSLanosterol, non-derivatized, GC-MS Spectrumsplash10-0a4l-4910000000-0fe7f84c95ab0a849fe9Spectrum
GC-MSLanosterol, non-derivatized, GC-MS Spectrumsplash10-0a4l-2910000000-c67a1f122f33698a14f6Spectrum
Predicted GC-MSLanosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-1009400000-e2b516142f5128a7b5f6Spectrum
Predicted GC-MSLanosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3002900000-35e63c0bf6f033cb847cSpectrum
Predicted GC-MSLanosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLanosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0a6r-0110900000-5e42e1f2d9ad534c003c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0a4i-0230900000-10f58fa6e118cd7c59972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-1791800000-178153ad92eececb33c42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0a4i-2980300000-6ce95c7f8b15b35475af2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-0a4j-2950100000-48f86ff7a22c596aa44d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0592-3940000000-c35d0cb6a2e4e291e8f82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-0592-3920000000-d717fdd3322a881bef992020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-0592-4910000000-4c6d07e3a8e48ae885802020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0a4j-5900000000-4c8b72037dbeae9a46d12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-067m-8900000000-522b8688d50362297c412020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 62V, positivesplash10-0aou-9700000000-70d433827c1a6dab0c412020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-05ox-9500000000-5b122dea636d3e3b59162020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 90V, positivesplash10-05r3-9500000000-0c1c5cbd994f8406f30e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 111V, positivesplash10-05r3-9600000000-5cb8ae11d071fa19f2062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0ktf-0392000000-03cda521ce6e102d92e42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-059j-2900000000-8086693fb040e5ed75012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0a4i-4900000000-c58ff2dc28c6ba6399972020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-01vk-0900000000-805937445cceda0cd70a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 29V, positivesplash10-0aor-0900000000-22d304b445b737121aa72020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-2cfcf7ce4b5b21140eae2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdi-2139500000-9a25961000db9796d6da2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-4259100000-9f7f26265abec4122e352016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-77a57cecc2069bee19262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-5b0f06bf8120e780e30c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-421e305d47b29da427d22016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
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.