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Record Information
Version4.0
Creation Date2008-08-13 10:51:01 UTC
Update Date2017-09-27 08:24:48 UTC
HMDB IDHMDB0006839
Secondary Accession Numbers
  • HMDB06839
Metabolite Identification
Common Name24,25-Dihydrolanosterol
Description24,25-Dihydrolanosterol is involved in the biosynthesis of steriods. 24,25-Dihydrolanosterol is reversibly converted to lanosterol by delta24-sterol reductase [EC:1.3.1.72].
Structure
Thumb
Synonyms
ValueSource
LanostenolChEBI
(3beta,20S)-Isomer OF lanostenolMeSH
(3beta,5XI,14xi)-isomer OF lanostenolMeSH
5 alpha-Lanost-8-en-3 beta-olMeSH
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name24,25-dihydrolanosterol
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
DescriptionThis compound 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

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-2964200000-c6d292b0916d62ea8526View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06r6-9720200000-8c73cf86594c8bf58e5dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4m-2911000000-583cb85e7235ac83846dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0002900000-b6caf9510eaf7f5d77a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vr-5149500000-411cd14a48ee6ca81905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7139100000-af6f3530e7230f55ca5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-a78041e281b8666a6d8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-019027469288cff3e4dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-2009500000-1e22a1853a0758a79a68View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot Available
Displaying entries 1 - 5 of 23 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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
Lanosterin + NADPH + Hydrogen Ion → 24,25-Dihydrolanosterol + NADPdetails