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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 10:51:01 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006839
Secondary Accession Numbers
  • HMDB06839
Metabolite Identification
Common Name24,25-Dihydrolanosterol
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.
Structure
Data?1582752409
Synonyms
ValueSource
LanostenolChEBI
(3beta,20S)-Isomer OF lanostenolHMDB
(3beta,5XI,14xi)-isomer OF lanostenolHMDB
5 alpha-Lanost-8-en-3 beta-olHMDB
Chemical FormulaC30H52O
Average Molecular Weight428.7333
Monoisotopic Molecular Weight428.401816286
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number79-62-9
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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.98ALOGPS
logP8.11ChemAxon
logS-6.4ALOGPS
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
Polarizability55.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.23631661259
DarkChem[M-H]-203.19431661259
DeepCCS[M-2H]-238.87130932474
DeepCCS[M+Na]+213.27130932474
AllCCS[M+H]+215.232859911
AllCCS[M+H-H2O]+213.432859911
AllCCS[M+NH4]+216.832859911
AllCCS[M+Na]+217.332859911
AllCCS[M-H]-210.332859911
AllCCS[M+Na-2H]-212.832859911
AllCCS[M+HCOO]-215.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
24,25-Dihydrolanosterol[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])CC33101.1Standard polar33892256
24,25-Dihydrolanosterol[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])CC33325.0Standard non polar33892256
24,25-Dihydrolanosterol[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])CC33291.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
24,25-Dihydrolanosterol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]1CC33339.5Semi standard non polar33892256
24,25-Dihydrolanosterol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]1CC33549.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol EI-B (Non-derivatized)splash10-0002-2964200000-c6d292b0916d62ea85262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol EI-B (Non-derivatized)splash10-06r6-9720200000-8c73cf86594c8bf58e5d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol GC-EI-TOF (Non-derivatized)splash10-0a4m-2911000000-583cb85e7235ac83846d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol EI-B (Non-derivatized)splash10-0002-2964200000-c6d292b0916d62ea85262018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol EI-B (Non-derivatized)splash10-06r6-9720200000-8c73cf86594c8bf58e5d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 24,25-Dihydrolanosterol GC-EI-TOF (Non-derivatized)splash10-0a4m-2911000000-583cb85e7235ac83846d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24,25-Dihydrolanosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2009700000-9daf045c9466c158bfdc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24,25-Dihydrolanosterol GC-MS (1 TMS) - 70eV, Positivesplash10-0079-3002900000-8f7b1a32f2ba2b44c8862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24,25-Dihydrolanosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24,25-Dihydrolanosterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 10V, Positive-QTOFsplash10-03fr-0002900000-b6caf9510eaf7f5d77a12016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 20V, Positive-QTOFsplash10-06vr-5149500000-411cd14a48ee6ca819052016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 40V, Positive-QTOFsplash10-0a4i-7139100000-af6f3530e7230f55ca5f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 10V, Negative-QTOFsplash10-004i-0000900000-a78041e281b8666a6d8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 20V, Negative-QTOFsplash10-004i-0000900000-019027469288cff3e4db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 40V, Negative-QTOFsplash10-01ot-2009500000-1e22a1853a0758a79a682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 10V, Positive-QTOFsplash10-004i-9102800000-e68b28d1d8c37f5b2fd52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 20V, Positive-QTOFsplash10-0a6r-9121300000-99597bbf71b616f6496b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 40V, Positive-QTOFsplash10-0avl-9643000000-fc3e8e224659df0644ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 10V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 20V, Negative-QTOFsplash10-004i-0000900000-ed006f256d0151ef06142021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24,25-Dihydrolanosterol 40V, Negative-QTOFsplash10-004i-0000900000-f875a9421ee03ba66ef72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004614
KNApSAcK IDC00023781
Chemspider ID389460
KEGG Compound IDC05109
BioCyc IDCPD-8606
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440560
PDB IDNot Available
ChEBI ID28113
Food Biomarker OntologyNot Available
VMH IDC05109
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Lanosterol + NADPH + Hydrogen Ion → 24,25-Dihydrolanosterol + NADPdetails