Showing Compound Card for δ 8,14 -Sterol (CDB005334)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:32:47 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005334
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameδ 8,14 -Sterol
DescriptionDelta 8,14 -Sterol, also known as δ8,14 -sterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, Delta 8,14 -sterol is considered to be a sterol lipid molecule. Delta 8,14 -Sterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. δ 8,14 -Sterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
delta8,14 -SterolChEBI
delta8,14-SterolChEBI
Δ8,14 -sterolGenerator
Δ8,14-sterolGenerator
Δ 8,14 -sterolGenerator
4-alpha-Methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-olHMDB
4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-olHMDB
4a-Methylergosta-8,14,24(241)-trien-3b-olHMDB
4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-olHMDB
(3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-olHMDB
(3β,4α,5α)-4-Methylergosta-8,14,24(28)-trien-3-olHMDB
4alpha-Methylergosta-8,14,24(241)-trien-3beta-olHMDB
4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-olHMDB
4α-Methylergosta-8,14,24(241)-trien-3β-olHMDB
Chemical FormulaC29H46O
Average Molecular Weight410.67
Monoisotopic Molecular Weight410.3549
IUPAC Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
CAS Registry Number74635-33-9
SMILES
[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1
InChI KeyHLAWVOWADPNAGN-BAHZUFOISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7ALOGPS
logP6.97ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130 m³·mol⁻¹ChemAxon
Polarizability53.06 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-MSδ 8,14 -Sterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-0009000000-3be06a7a2e1d781b5fa8Spectrum
Predicted GC-MSδ 8,14 -Sterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gb9-2003900000-1ddc0b2fd8c5c5050903Spectrum
Predicted GC-MSδ 8,14 -Sterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1019500000-046d99a719521520a2212016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053u-5239100000-35e12a7ac241ea6b3d5e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-7179000000-157b7d71a0b50a4f6cfa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3112227426dc5f73b5982016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0004900000-6302f767a4949cfeabe02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2009000000-1068ac4ee572fe372b162016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0079400000-909cacfa5264a8b970532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5295000000-8fdfbe980fb0780691312021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9431000000-dd7d0e22284f4ddcce4c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-bf8e63a2888265bea2de2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-7b92331f9804da3440ed2021-09-22View 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 IDHMDB0006928
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011216
KNApSAcK IDC00007523
Chemspider ID391501
KEGG Compound IDC11508
BioCyc IDALPHA-METHYL-5-ALPHA-ERGOSTA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443237
PDB IDNot Available
ChEBI ID30109
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