Showing metabocard for 4,4-Dimethylcholesta-8,14,24-trienol (BMDB0001023)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:02 UTC
Update Date2020-05-21 16:28:43 UTC
BMDB IDBMDB0001023
Secondary Accession Numbers
  • BMDB01023
Metabolite Identification
Common Name4,4-Dimethylcholesta-8,14,24-trienol
Description4,4-Dimethylcholesta-8,14,24-trienol, also known as FF-MAS or follicular fluid meiosis activating sterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4,4-dimethylcholesta-8,14,24-trienol is considered to be a sterol. Based on a literature review very few articles have been published on 4,4-Dimethylcholesta-8,14,24-trienol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,4-Dimechol-8,14,24-trienolChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3beta-olChEBI
4,4-Dimethylcholesta-8(9),14,24-trien-3b-olGenerator
4,4-Dimethylcholesta-8(9),14,24-trien-3β-olGenerator
FF-MASMeSH
Follicular fluid meiosis activating sterolMeSH
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-olMeSH
(3beta,5alpha)-4,4-Dimethyl-cholesta-8,14,24-trien-3-olHMDB
(3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-olHMDB
4,4'-Dimethyl cholesta-8,14,24-triene-3-beta-olHMDB
4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-olHMDB
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-olHMDB, MeSH
4,4-Dimethyl-cholesta-8,14,24-trienolHMDB
Chemical FormulaC29H46O
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
IUPAC Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
CAS Registry Number64284-64-6
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
InChI Identifier
InChI=1S/C29H46O/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/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1
InChI KeyLFQXEZVYNCBVDO-PBJLWWPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ALOGPS
logP7ChemAxon
logS-5.6ALOGPS
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
Refractivity130.92 m³·mol⁻¹ChemAxon
Polarizability52.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1009000000-416b93fbfcc925dc4766View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-4103900000-a8896cb66364cceda294View 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0006-1329000000-9b8610b57655e3a41ca1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-3958000000-39386b42d7d020c29bbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-05o3-4943000000-68305bc3d9c2e79f17bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-067j-4931000000-17ac98d22705a30ac479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0aos-4930000000-57d6f877cf0915f132b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-0aos-5910000000-64fc1bcaeb9b8921df29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-0aou-5900000000-7ebf0af9fd57cfad6303View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 57V, positivesplash10-0ar3-4900000000-2533caeaeb9ebdebc4a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 70V, positivesplash10-054o-4900000000-bbdc94435c78cc8bc333View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 83V, positivesplash10-056u-4900000000-36892883de61aea8c544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 102V, positivesplash10-00ou-4900000000-18c114c240680434a0d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-053r-0393000000-0c6dea5c7ec2bee79e1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-000l-0970000000-b2c5bf7eb779387cd981View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0930000000-e231f282c3639a162ab0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0aor-2900000000-85f247eedd1281442c90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0950000000-15e1c7c9cb681913720eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0api-0900000000-eb024b4e1b55ee575bb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0a4i-0900000000-6034a459e48936a045ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3773f1780255ea800890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0005900000-43378c95eaacf13d3cd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1009000000-1387c3c0fba5a00f56a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd7741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd7741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0013900000-62d1d4a75b4aa2cd0a6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0019500000-5b93d5ee5e25639470f1View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001023
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022376
KNApSAcK IDNot Available
Chemspider ID391478
KEGG Compound IDC11455
BioCyc IDNot Available
BiGG ID1454719
Wikipedia LinkNot Available
METLIN ID5952
PubChem Compound443212
PDB IDNot Available
ChEBI ID17813
References
Synthesis ReferenceRuan B; Wilson W K; Schroepfer G J Jr An alternative synthesis of 4,4-dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol, an intermediate in sterol biosynthesis and a reported activator of meiosis and of nuclear orphan receptor LXR alpha. Bioorganic & medicinal chemistry letters (1998), 8(3), 233-6.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol 14-alpha demethylase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in sterol biosynthesis. Catalyzes 14-alpha demethylation of lanosterol and 24,25-dihydrolanosterol likely through sequential oxidative conversion of 14-alpha methyl group to hydroxymethyl, then to carboxylaldehyde, followed by the formation of the delta 14,15 double bond in the sterol core and concomitant release of formic acid. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP51A1
Uniprot ID:
Q4PJW3
Molecular weight:
56596.0
Reactions
Lanosterin + 3 Oxygen + 3 NADPH → 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid +3 NADP +4 Waterdetails
Enzyme Details
2. Delta(14)-sterol reductase TM7SF2
General function:
Involved in delta14-sterol reductase activity
Specific function:
Catalyzes the reduction of the C14-unsaturated bond of lanosterol, as part of the metabolic pathway leading to cholesterol biosynthesis.
Gene Name:
TM7SF2
Uniprot ID:
Q8WMV1
Molecular weight:
46751.0
Reactions
4,4-Dimethylcholesta-8,14,24-trienol + NADPH → 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPdetails