Showing Compound Card for 4,4-Dimethylcholesta-8,14,24-trienol (CDB005329)

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Record Information
Version1.0
Created at2020-04-17 19:32:17 UTC
Updated at2020-12-07 19:11:57 UTC
CannabisDB IDCDB005329
Secondary Accession NumbersNot Available
Cannabis Compound 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 lipid molecule. 4,4-Dimethylcholesta-8,14,24-trienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4,4-Dimethylcholesta-8,14,24-trienol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight410.67
Monoisotopic Molecular Weight410.3549
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

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
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4,4-Dimethylcholesta-8,14,24-trienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-1009000000-416b93fbfcc925dc4766Spectrum
Predicted GC-MS4,4-Dimethylcholesta-8,14,24-trienol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-4103900000-a8896cb66364cceda294Spectrum
Predicted GC-MS4,4-Dimethylcholesta-8,14,24-trienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4,4-Dimethylcholesta-8,14,24-trienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0006-1329000000-9b8610b57655e3a41ca12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-3958000000-39386b42d7d020c29bbb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-05o3-4943000000-68305bc3d9c2e79f17bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-067j-4931000000-17ac98d22705a30ac4792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-0aos-4930000000-57d6f877cf0915f132b32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-0aos-5910000000-64fc1bcaeb9b8921df292020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-0aou-5900000000-7ebf0af9fd57cfad63032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 57V, positivesplash10-0ar3-4900000000-2533caeaeb9ebdebc4a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 70V, positivesplash10-054o-4900000000-bbdc94435c78cc8bc3332020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 83V, positivesplash10-056u-4900000000-36892883de61aea8c5442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 102V, positivesplash10-00ou-4900000000-18c114c240680434a0d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-053r-0393000000-0c6dea5c7ec2bee79e1e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-000l-0970000000-b2c5bf7eb779387cd9812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0930000000-e231f282c3639a162ab02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0aor-2900000000-85f247eedd1281442c902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-006t-0950000000-15e1c7c9cb681913720e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0api-0900000000-eb024b4e1b55ee575bb22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 28V, positivesplash10-0a4i-0900000000-6034a459e48936a045eb2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3773f1780255ea8008902016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0005900000-43378c95eaacf13d3cd42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1009000000-1387c3c0fba5a00f56a62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0013900000-62d1d4a75b4aa2cd0a6f2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0019500000-5b93d5ee5e25639470f12016-09-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Delta(14)-sterol reductaseTM7SF211q13O76062 details
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001023
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Delta(14)-sterol reductase
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
Enzyme Details
2. Lanosterol 14-alpha demethylase
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81