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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:09 UTC
HMDB IDHMDB0001286
Secondary Accession Numbers
  • HMDB01286
Metabolite Identification
Common Name4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol
Description4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol, also known as 14-demethyllanosterol or 4,4-dimethyl-8,24-cholestadienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752189
Synonyms
ValueSource
(3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-olHMDB
14-DemethyllanosterolHMDB
4,4-Dimethyl-5 alpha -cholesta-8,24-dien-3 beta -olHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-olHMDB
4,4-Dimethyl-5-alpha-cholesta-8,24-dien-3-beta-olHMDB
4,4-Dimethyl-5a-cholesta-8,24-dien-3b-olHMDB
4,4-Dimethyl-5alpha -cholesta-8,24-dien-3-beta -olHMDB
4,4-Dimethyl-5alpha-cholest-7-en-3beta-olHMDB
4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-olHMDB
4,4-Dimethyl-8,24-cholestadienolHMDB
4,4-DimethylzymosterolHMDB
4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomerHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry Number7448-02-4
SMILES
[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1
InChI KeyCHGIKSSZNBCNDW-GKBRUXRCSA-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
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.00054 g/LALOGPS
logP7.14ALOGPS
logP7.41ChemAxon
logS-5.9ALOGPS
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
Refractivity130.07 m³·mol⁻¹ChemAxon
Polarizability53.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pk-1009000000-715a7edb03ab16ddaa67Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06di-3003900000-b4d1997a0f59b226076eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-5831f1297a9ddaefca1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2139100000-1571d65e1b255cf2e4d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0170-3339000000-9b79492ac4a81d9025ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-e0f073ba6b1bddb613bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-276fec1a6d98e42e92a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1009000000-9afa67f4cfe32f1b2acdSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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
FoodDB IDFDB022534
KNApSAcK IDNot Available
Chemspider ID25994967
KEGG Compound IDC05108
BioCyc IDNot Available
BiGG ID45128
Wikipedia LinkNot Available
METLIN ID6135
PubChem Compound50990081
PDB IDNot Available
ChEBI ID18364
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP → 4,4-Dimethylcholesta-8,14,24-trienol + NADPHdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP → 4,4-Dimethylcholesta-8,14,24-trienol + NADPH + Hydrogen Iondetails
General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen → 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol + NADP + Waterdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADH + Hydrogen Ion + Oxygen → 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD + Waterdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen → 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NADP + Waterdetails
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
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADPdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
C5orf4
Uniprot ID:
Q96IV6
Molecular weight:
Not Available
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen → 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol + NADP + Waterdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADH + Hydrogen Ion + Oxygen → 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD + Waterdetails
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen → 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NADP + Waterdetails