Record Information
Version1.0
Creation date2010-04-08 22:06:19 UTC
Update date2018-05-28 22:44:59 UTC
Primary IDFDB004614
Secondary Accession Numbers
  • FDB005166
Chemical Information
FooDB Name3beta-Lanostenol
Description24,25-Dihydrolanosterol, also known as lanostenol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 24,25-dihydrolanosterol is considered to be a sterol lipid molecule. 24,25-Dihydrolanosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number79-62-9
Structure
Thumb
Synonyms
SynonymSource
LanostenolChEBI
(3beta,20S)-Isomer OF lanostenolHMDB
(3beta,5XI,14xi)-isomer OF lanostenolHMDB
5 alpha-Lanost-8-en-3 beta-olHMDB
(3beta)-Lanost-8-en-3-olbiospider
24-Dihydrolanosterolbiospider
24,25-Dihydrolanosterolbiospider
3b-Lanostenoldb_source
4,4,14-Trimethylcholest-8-en-3beta-olmanual
Dihydrolanosteroldb_source
Lanost-8-en-3beta-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.98ALOGPS
logP8.11ChemAxon
logS-6.5ALOGPS
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 Count5ChemAxon
Refractivity133.69 m³·mol⁻¹ChemAxon
Polarizability55.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H52O
IUPAC name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
InChI IdentifierInChI=1S/C30H52O/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/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
InChI KeyMBZYKEVPFYHDOH-BQNIITSRSA-N
Isomeric SMILES[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3
Average Molecular Weight428.7333
Monoisotopic Molecular Weight428.401816286
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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNeedles (MeOH)CCD
Mass CompositionNot Available
Melting PointMp 148° (146°)CCD
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a] 19D +63 ( CHCl3)CCD
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2964200000-c6d292b0916d62ea8526JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06r6-9720200000-8c73cf86594c8bf58e5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4m-2911000000-583cb85e7235ac83846dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2964200000-c6d292b0916d62ea8526JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06r6-9720200000-8c73cf86594c8bf58e5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4m-2911000000-583cb85e7235ac83846dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2009700000-9daf045c9466c158bfdcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-3002900000-8f7b1a32f2ba2b44c886JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0002900000-b6caf9510eaf7f5d77a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vr-5149500000-411cd14a48ee6ca81905JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7139100000-af6f3530e7230f55ca5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-a78041e281b8666a6d8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-019027469288cff3e4dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-2009500000-1e22a1853a0758a79a68JSpectraViewer
ChemSpider ID389460
ChEMBL IDNot Available
KEGG Compound IDC05109
Pubchem Compound ID440560
Pubchem Substance IDNot Available
ChEBI ID28113
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06839
CRC / DFC (Dictionary of Food Compounds) IDLXM30-K:LXM33-N
EAFUS IDNot Available
Dr. Duke ID24-DIHYDROLANOSTEROL|LANOSTENOL|LANOST-8-EN-3-BETA-OL
BIGG IDNot Available
KNApSAcK IDC00023781
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).