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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:10 UTC
HMDB IDHMDB01286
Secondary Accession NumbersNone
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 (14-demethyllanosterol) is an intermediate in sterol biosynthesis. In particular, it is an intermediate in the conversion of lanosterol to zymosterol. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is a substrate for C-4 methyl sterol oxidase, NAD(P)-dependent steroid dehydrogenase, Cytochrome P450 51A1 and Delta(14)-sterol reductase.
Structure
Thumb
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
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 KeyInChIKey=CHGIKSSZNBCNDW-GKBRUXRCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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 Solubility0.000544 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.07 m3·mol-1ChemAxon
Polarizability53.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Alendronate pathwaySMP00095Not Available
Atorvastatin PathwaySMP00131Not Available
Cerivastatin PathwaySMP00111Not Available
CHILD SyndromeSMP00387Not Available
Cholesteryl ester storage diseaseSMP00508Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)SMP00388Not Available
DesmosterolosisSMP00386Not Available
Fluvastatin PathwaySMP00119Not Available
Hyper-IgD syndromeSMP00509Not Available
HypercholesterolemiaSMP00209Not Available
Ibandronate PathwaySMP00079Not Available
Lovastatin PathwaySMP00099Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)SMP00319Not Available
Mevalonic aciduriaSMP00510Not Available
Pamidronate PathwaySMP00117Not Available
Pravastatin PathwaySMP00089Not Available
Risedronate PathwaySMP00112Not Available
Rosuvastatin PathwaySMP00092Not Available
Simvastatin Action PathwaySMP00082Not Available
Smith-Lemli-Opitz Syndrome (SLOS)SMP00389Not Available
Steroid BiosynthesisSMP00023map00100
Wolman diseaseSMP00511Not Available
Zoledronate PathwaySMP00107Not Available
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 IDFDB022534
KNApSAcK IDNot Available
Chemspider ID25994967
KEGG Compound IDC05108
BioCyc ID44-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET
BiGG ID45128
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01286
Metagene LinkHMDB01286
METLIN ID6135
PubChem Compound50990081
PDB IDNot Available
ChEBI ID18364
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