4,4-Dimethylcholesta-8,14,24-trienol (CHEM035035)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:26:06 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035035
Identification
Common Name4,4-Dimethylcholesta-8,14,24-trienol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass410.675 g/mol
Monoisotopic Mass410.355 g/mol
CAS Registry Number64284-64-6
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
SMILES[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1009000000-416b93fbfcc925dc4766Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-4103900000-a8896cb66364cceda294Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0006-1329000000-9b8610b57655e3a41ca1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-3958000000-39386b42d7d020c29bbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-05o3-4943000000-68305bc3d9c2e79f17bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-067j-4931000000-17ac98d22705a30ac479Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0aos-4930000000-57d6f877cf0915f132b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-0aos-5910000000-64fc1bcaeb9b8921df29Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-0aou-5900000000-7ebf0af9fd57cfad6303Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 57V, positivesplash10-0ar3-4900000000-2533caeaeb9ebdebc4a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 70V, positivesplash10-054o-4900000000-bbdc94435c78cc8bc333Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 83V, positivesplash10-056u-4900000000-36892883de61aea8c544Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 102V, positivesplash10-00ou-4900000000-18c114c240680434a0d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-053r-0393000000-0c6dea5c7ec2bee79e1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-000l-0970000000-b2c5bf7eb779387cd981Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0930000000-e231f282c3639a162ab0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0aor-2900000000-85f247eedd1281442c90Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0950000000-15e1c7c9cb681913720eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0api-0900000000-eb024b4e1b55ee575bb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0a4i-0900000000-6034a459e48936a045ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3773f1780255ea800890Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0005900000-43378c95eaacf13d3cd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1009000000-1387c3c0fba5a00f56a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd7741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd7741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0013900000-62d1d4a75b4aa2cd0a6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0019500000-5b93d5ee5e25639470f1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001023
FooDB IDFDB022376
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1454719
BioCyc IDNot Available
METLIN ID5952
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID391478
ChEBI ID17813
PubChem Compound ID443212
Kegg Compound IDC11455
YMDB IDYMDB00268
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ruan 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.
2. Ruan B, Watanabe S, Eppig JJ, Kwoh C, Dzidic N, Pang J, Wilson WK, Schroepfer GJ Jr: Sterols affecting meiosis: novel chemical syntheses and the biological activity and spectral properties of the synthetic sterols. J Lipid Res. 1998 Oct;39(10):2005-20.