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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:16 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 (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
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[8.7.0.0^{2,7}.0^{11,15}]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[8.7.0.0^{2,7}.0^{11,15}]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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Polarizability53.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available200.81931661259
DarkChem[M-H]-PredictedNot Available201.40931661259
AllCCS[M+H]+PredictedNot Available210.82232859911
AllCCS[M-H]-PredictedNot Available211.61232859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol,1TMS,#13317.8792https://arxiv.org/abs/1905.12712
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol,1TBDMS,#13522.1858https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pk-1009000000-715a7edb03ab16ddaa672017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06di-3003900000-b4d1997a0f59b226076e2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-5831f1297a9ddaefca1b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2139100000-1571d65e1b255cf2e4d32016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0170-3339000000-9b79492ac4a81d9025ec2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-e0f073ba6b1bddb613bc2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-276fec1a6d98e42e92a12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1009000000-9afa67f4cfe32f1b2acd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009700000-803cd9d3863583645c292021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9527100000-d4f09426d4583ec16d0b2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9743000000-3166c978b6fe24ddec4b2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-1015900000-96469d6e79efcdc91ee92021-09-09View Spectrum
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
FooDB 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
MarkerDB 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